Organic Chemistry

Aliphatics are __________

(a) compounds that do not contain a benzene ring (b) and can be saturated or unsaturated

The (a)____________ in Sn1 reaction can attack from any position in the second step because the carbocation has a (b)________ shape, this means that Sn1 mechanism is described as(c) ____________.

(a) nucleophile (b) planar (c) non-stereospecific

A (a) ________ is a measuring (b) ________ that allows the (c) ________ & ________ of such (RF268) a (d) ________ to be (e) m________. It consists of, in order, a (f) ________, (g) ________ ________, (h) ________ ________ in container, and an (i) ________:

(a) polarimeter (b) instrument (c) amount & direction (d) rotation (e) measured (f) polarizer (g) plane-polarized light (h) sample solution (i) analyser

A (a) ________ measures the (b) ________ ________ of a given sample

(a) polarimeter (b) optical activity

(a)____________waves cause molecules to increase their rotational energy. This can information about (b)__________

(a)Microwaves (b)bond lengths

The vertical heights of the steps in the integration trace are proportional to the number of (a)______________ in each enivronment. The horizontal scale on the NMR spectrum is the (b)_________________

(a)hydrogen atoms (b)chemical shift

Suffix in IUPAC name for amine

-anamine

Suffix in IUPAC name for alkene

-ene

Physical properties of alkanes

1. Gas at room temp 2. Does not dissolve in water 3. Colourless 4. Does not react with acids/bases 5. Does not react with oxidising agents

This homologous series has the suffix "al"

Aldehyde

Reflux

Allows heating without pressure build up and traps all reacting species & products in flask.

Draw the condensed structural formula of 2,3-dimethylpentane.

CH3CH(CH3)CH(CH3)CH2CH3

By the condensation reaction known as esterification between and alcohol and a carboxylic acid, _________ are formed.

Esters

Naming carboxylic acids

Functional group always at the end of the chain, therefore no need for numbers. Name will be corresponding stem + '-anoic acid'

Step 3 for naming compounds

Identify each FUNCTIONAL group by its appropriate 'prefix' or 'suffix' and its position by the number of the carbon atom it is attached to.

Tertiary Alcohol

It has three C atoms attached to the C with the -OH group.

This homologous series has the suffix "one"

Ketone

What is the functional group for amines?

NH₂

Use of H^1NMR

NMR is used to determine hydrogen proton environments based on their chemical shift and abundance # of peaks = # of proton environments Relative integral proportions = proportion of hydrogen protons Used to deduce how many hydrogens are there in 1 environment. # of small peaks per large peak = neighbouring protons.

General formula for ketones

R-CO-R'

How does complete oxidation of a primary alcohol occur?

The reaction mixture must be refluxed.

Heterolytic fission

When a covalent bond breaks with both the shared electrons going to one of the products. It produces two oppositely charged ions. X:X→X: negative +Xpositive.

Exam tip:major minor

When asked to predict and explain the major product when a hydrogen halide adds to an alkene, always explain it in terms of the stability of the intermediate carbocation - it is never enough to just say 'Markovnikov's rule'. You must also make sure that you include a comparison - there are more electron-releasing alkyl groups around the positively charged carbon in a secondary carbocation than in a primary carbocation

Electrophilic addition reaction

an addition reaction in which the first species that adds to the reactant is an electrophile.

Benzene rings are very stable because the orbitals overlap, creating __________ electrons in a ring.

delocalised

Double-barbed curly arrow

represents the motion of an electron pair

Fish-hook(a half or only one arrow head) curly arrow

represents the movement of a single electron

Full structural formula

shows all the bonds in the molecule. Eg; for Propane

Suffix in IUPAC name for alkynes

ynes

Primary, secondary and tertiary amines

• primary amines contain the -NH2 functional group • secondary amines contain -NHR (where 'R' represents an alkyl group) • tertiary amines contain -NR2

'E/Z' isomerism is based on the (a) ________ (b) ________ of ________, which are applied to the (c) ________ on (d) e________ e________ of the (e) ________ bond / the (f) ________ points of the (g) c_______ r_______

(a) 'Cahn-Ingold-Prelog' (b) rules of priority (c) groups of atoms (d) each end (e) double (f) relevant (g) cyclic ring

(R220) Mnemonic: 'E' is for (a) ________ ([across' the (b) r_______e p______e]; Thus, not 'E'-cross the (b) ________ ________ is (c) '___'

(a) 'E'-cross (b) reference plane (c) 'Z'

(RF189) The prefixes (a) 'c________ and (b) 't________ come (c) ________ the (d) ________ name of the compound respectively

(a) 'cis-' (b) 'trans-' (c) before (d) IUPAC

(RF272) When drawing the (a) _____ _____, make sure the (b) ________ of ________s the (c) c________ ________ are bonded to are illustrated in their (d) ________ ________ f________ or (e) ________ f________, instead of their (f) ________ ________ f________ for (g) s________, unless the Q^n (h) e________ o________.

(a) 1st enantiomer (b) groups of atoms (c) chiral carbon (d) condensed structural formulae (e) molecular formulae (f) full structural formulae (g) simplicity (h) explicates otherwise

(R207) When a given compound contains (a) ________ different (b) ________ / (c) ________ attached to the double bond / the cyclic ring, these can be (d) ________ to give (e) ________ (f) d________' cis-trans & E/Z' isomers of the same compound.

(a) 2 or more (b) substituents (c) groups of atoms (d) arranged (e) at least 2 (f) different

(a) ________ compounds are (a) i_______ ________ with a (b) m_______ i_______ of themselves. They have (d) a______ l______ ______ (e) ________ p________ of symmetry

(a) Achiral (b) identically superimposable (c) mirror image (d) at least 1 (e) internal plane

(a)________ hydrocarbons consist of one or more chains of connected carbon atoms. Simply,(a)________hydrocarbons do not contain any rings.

(a) Acyclic

Aldehydes and ketones contain the (b)_________ (C=O) functional group

(a) Carbonyl

(a) C________l isomerism: (b)__________rs of the (c) s________ given compound that can be (d) _________ (e) o______ by (f) __________ and (g) r__________ (h) __________ bonds. I.e., there are (i) p_________ different (j) __________ between corresponding (a)__________ isomers which may, subsequently, possess distinct (k) __________.

(a) Configurational (b) stereoisomers (c) same (d) interconverted (e) only (f) breaking (g) reforming (h) covalent (i) permanently (j) geometries (k) properties

(a) C__________l isomerism: (b)__________mers of the (c) s__________ given compound that can (spontaneously) be (d) i__________d via (e) f__________ about (f)__________-bonds. Some (g) c_________s of a compound may be more (h)__________ and, thus, (i)__________ than others.

(a) Conformational (b) stereoisomers (c) same (d) interconverted (e) free rotation (f) 'sigma' (g) conformers (h) stable (i) favored

Unsaturated hydrocarbons

(a) Contains double or triple covalent (b) E.g.: Alkenes, Alkynes, & more

Saturated hydrocarbons

(a) Contains only single covalent bonds (b) E.g.: Alkanes, Cycloalkanes, Alcohols, & more

(a)________ hydrocarbons have at least some of their carbon atoms connected together to form one or more rings.

(a) Cyclic

(RF253) (a) ________ enantiomers of the same compound undergo (a) ________ (c) ________ reactions and have (a) ________ (c) ________ properties in (d) ________ environments

(a) Different (b) same (c) chemical (d) chiral

(a) ________ diastereomers of the (b) ________ compound (c) ________ from each other in their (d) ________ and chemical properties

(a) Different (b) same (c) differ (d) physical

(R253) (a) ________ enantiomers of the (b) ________ given compound (c) ________ the (d) ________ of oscillation of plane-polarized light in (e) ________ d________ by (f) ________ amounts, (g) p_______ that the (h) ________ _______, the (i) ________ of (j) l________ ________, and the (k) ________ ________ ________ are kept (l) c________. (m) S________ ________ of these enantiomers are both called (n) o________ ________.

(a) Different (b) same (c) rotate (d) plane (e) opposite directions (f) equal (g) provided (h) solution concentration (i) wavelength (j) light used (k) sample path length (l) constant (m) Separate solutions (n) optically active

cis-trans and (a) __________ism: (b)__________rs that (c) e__________ (d) o__________ when there is (e) r__________ __________n around (f) __________.

(a) E/Z isomerism (b) configurational isomers (c) exist (d) only (e) restricted rotation (f) atoms

(RF99) (a)__________ have particularly (b)__________ smells, but are (c)__________ and not (d)__________ or aromatic compounds.

(a) Esters (b) distinct (c) aliphatics (d) arenes

(RF207) Case 1: -(a) F___________ is not possible about the (b)___________, as it would (c)___________ otherwise. -The (d) ___________ passes (e) ___________ through the double bond

(a) Free rotation (b) 'pi'-bond (c) break (d) reference plane (e) horizontally

(a)__________ have a higher (b)__________ and lower (c)__________ than aldehydes with the same (d)__________. This is because the (e)__________ ('C=O') of (a) __________ are more (f)__________ than those of aldehydes. Thus, the (g)__________ in the 'C=O' groups of ketones are subject to (h) g________r (i)__________ than those faced by (g)__________ in the 'C=O' groups of aldehydes and are, hence, (j) __________

(a) Ketones (b) boiling point (c) volatility (d) molecular formula (e) carbonyl groups (f) polarized (g) carbons (h) greater (i) steric hindrance (j) more stable

Aldehydes have intermolecular __________

(a) London dispersion forces of attraction (b) permanent dipole-dipole interactions

Halogenoalkanes have intermolecular __________

(a) London dispersion forces of attraction (b) permanent dipole-dipole interactions

Ketones have intermolecular __________

(a) London dispersion forces of attraction (b) permanent dipole-dipole interactions

Alcohols have intermolecular __________

(a) London dispersion forces of attraction (b) permanent dipole-dipole interactions (c) hydrogen bonding

Carboxylic acids have intermolecular __________

(a) London dispersion forces of attraction (b) permanent dipole-dipole interactions (c) hydrogen bonding

(a) O__________ __________m: (b) __________rs that (c) e_______ (d) ________ when there is (e) _______ or more (f) __________ (g) c__________ __________ [that have (h) __________ e__________ d__________].

(a) Optical isomerism (b) configurational isomers (c) exist (d) only (e) one (f) asymmetric (g) carbon (h) four electron domains

Enantiomers: (a) __________s of the same compound that have (b) __________ __________ at (c) __________ (d) c__________ c________ & are (e) __________ __________ i__________ of (f) __________ __________r.

(a) Optical isomers (b) opposite configurations (c) all (d) chiral carbons (e) non-superimposable mirror images (f) each other

(RF207) Case 1: -In general: for a given compound (R1-)(R2-)C=C(-R3)(-R4), where R1≠R2, (a)________, [R1,R2,R3, & R4 are all (b)________] and R1 & R3 are on opposite sides of the (c) r________ ________, it is the 'trans-' isomer of the compound and is referred to as ''trans-'+[IUPAC name of compound]' when (d) ________, or (e) ________4

(a) R3≠R4 (b) groups of atoms (c) reference plane (d) R1=R3 (e) R2=R4

(RF207) Case 1: -In general: for a given compound (R1-)(R2-)C=C(-R3)(-R4), where R1≠R2, (a)________, [R1,R2,R3, & R4 are all (b)________] and R1 & R3 are on opposite sides of the (c) ________ ________, it is the 'cis-' isomer of the compound and is referred to as ''cis-'+[IUPAC name of compound]' when (d) ________, or (e) ________3

(a) R3≠R4 (b) groups of atoms (c) reference plane (d) R1=R4 (e) R2=R3

(a) ________: separating (b) ________ enantiomers of the (c) ________ chiral compound from a (d) ________ mixture with respect to (e) ________ other.

(a) Resolution (b) different (c) same (d) racemic (e) each

Stereochemistry: (a) S___________ + (b) __________ --> Isomerism (c) ___________ + (d) D___________ --> (h) ___________ (e) ___________ + (f) ___________ --> (a) S___________ (h) ___________ + (g) ___________ --> (e) C___________

(a) Stereoisomerism (b) Structural isomerism (c) Enantiomers (d) Diastereomers (e) Configurational isomerism (f) Conformational isomerism (g) 'cis-trans & E/Z isomerism' (h) optical isomerism

(a) S________l isomerism: compounds that share the same (b) __________, but have (c) __________ and functional groups (d)__________ in (e)__________ ways.

(a) Structural (b) molecular formula (c) atoms (d) bonded together (e) non-identical / different

Catenation

(a) The ability to form bonds between atoms of the same element. (b) Catenation occurs very readily with carbon

(a) _______ crystal_______ can be used to identify the (b) _______ _______ and (c) _______ _______ of (d) _______ compounds

(a) X-ray crystallography (b) bond lengths (c) bond angles (d) crystalline

Primary Alcohols can be oxidized to carboxylic acids with (a) ___________ or (b) __________ (c) ___________

(a) acidified potassium manganate (VII) (b) acidified (c) potassium dichromate (VI)

Examples of some aliphatic compounds are (a) a__________es, (b) a__________es, and (c) a__________es

(a) alkanes (b) alkenes (c) amines

An (a) ________ is a (b) ________ of polarizer that enables the (c) ________ of plane-polarized light to be (d) ________: the (a) ________ can be (e) ________ until the (f) ________ (g) ________ of light (h) ________ through it, allowing the (i) ________ and (j) ________ [(k) ________ or anti-clockwise] of such a (c) ________ to be (d) ________.

(a) analyser (b) type (c) rotation (d) measured (e) rotated (f) emerging (g) beam (h) passes (i) extent (j) direction (k) clockwise

In a 1HNMR spectrum, the (a) ________ ________ a given (b) p________ indicates the (c) ______ _____ ______ in (d) e_______ _______ with respect to the (e) ________ ________ other peaks of the (f) ________ spectrum

(a) area under (b) peak (c) number of protons (d) each environment (e) areas under (f) same

All (a)__________ are (b)__________ compounds, but (c) __________ aromatic compounds are (a)__________

(a) arenes (b) aromatic (c) not all

'Planar' in the context of (a) __________ potentially refers to the (b) __________ atoms of the (c) __________ being all (d) __________. I.e., if even one (b)__________ atom of the (c)__________ of a given compound is sp3 or sp hybridized, the said compound is not considered (e) __________.

(a) aromaticity (b) carbon (c) cyclic ring (d) sp2 hybridized (e) planar

(RF260) A (a) b________ of (b) ________ l________ consists of (c) ________ w________ that (d) ________ in an (e) ________ n________ of (f) p________ at (g) ________ a________ to the (h) d________ of (i) t________.

(a) beam (b) ordinary light (c) electromagnetic waves (d) oscillate (e) infinite number (f) planes (g) right angles (h) direction (i) travel

When a (a) ________ of (b) ________ light passes through an (c) ________-a________ ________, the plane of (d) ________ of the (e) ________ (b) ________ light is (f) ________ by the sample solution

(a) beam (b) plane-polarized (c) optically-active solution (d) oscillation (e) initial (f) rotated

To note, in cycloalkanes, the (a) b______ ________s are (b) ________ from the (c) ________ angles in the parent alkane. E.g., the (d) ________ ________ in cyclopropane form a (d) ________ with (a) ________s of 60°

(a) bond angle (b) strained (c) tetrahedral (d) carbon atoms (e) triangle

A (a) ________ atom attached to (b) ________ (c) ________ (d) g________ of a________ is called (e) c________, (f) a________, or a (g) s________.

(a) carbon (b) four (c) different (d) groups of atoms (e) chiral (f) asymmetric (g) stereocenter

When the (a) _________ _________ of the double bond are bonded to (b) _____ _____ __ d______t s_______s in (c) t_________, the (d) _________ naming designation cannot be applied, and the more (e) c_________ (f) ____ naming system is (g) a_________ instead.

(a) carbon atoms (b) more than 2 different substituents (c) total (d) 'cis-trans' (e) comprehensive (f) 'E/Z' (g) adopted

(RF133) I.e., the (a)__________ groups of (b)__________ are more (c)__________ than those of aldehydes because of there being (d) ________ (e) __________ from the (f) __________ carbon groups for the carbon in the (k)__________ group in (b)__________ than the (e)__________ from the (g)________ carbon group for the same carbon in the 'C=O' group in aldehydes: (l)__________ have the (k)__________ group (h)__________ to a (i)__________ carbon, whereas (a)__________ have the 'C=O' group (h)__________ to a (j)__________ carbon respectively.

(a) carbonyl (b) ketones (c) polarized (d) greater (e) positive inductive effects (f) two adjacent (g) one adjacent (h) bonded (i) primary (j) secondary (k) 'C=O' (l) aldehydes

'cis-trans & E/Z isomerism' arise when (a) c___________ of a given compound become (b) ___________ relative to (c) ___________, due to some (d) ___________ in the compound that (e) r__________s the (e) ___________ of such groups of atoms.

(a) certain groups of atoms (b) fixed in space (c) each other (d) constraint (e) restricts (f) free rotation

(a) C________ compounds have no (b) ________ ________ of ________

(a) chiral (b) internal planes of symmetry

(RF216) When using 'E/Z' for a given (a) c________ (R1-)(R2-)C=C(-R3)(-R4) or (R1-)(R2-)C-C(sub. n-1)(-R3)(-R4), where R1≠R2, R3≠R4, [R1,R2,R3, & R4 are all (b)________], and R1 & R4 are on (c) o________ s_______ of the (c) r________ _______, neither R1 or R2 need be (d)________ from R3 or R4 (e)_______.

(a) compound (b) groups of atoms (c) opposite sides (c) reference plane (d) different (e) respectively

Isomerism: (a) __________ with the same (b)__________, but different (c)__________

(a) compounds (b) molecular formula (c) arrangements of atoms

Arenes are __________

(a) compounds that contain 1 or more benzene rings (b) and are all unsaturated compounds

(RF207) Case 2: for a given (a) _________ compound (R1-)(R2-)C-C(sub. 'n-1')(-R3)(-R4), where 'n' is the number of carbon atoms in the compound, R1≠R2, (b)________, [R1,R2,R3, & R4 are all (c)________] and R1 & R3 are on opposite sides of the (d) r________ ________, it is the 'trans-' isomer of the compound and is referred to as ''trans-'+[IUPAC name of compound]' when (e) ________, or (f) ________4.

(a) cyclic (b) R3≠R4 (c) groups of atoms (d) reference plane (e) R1=R3 (f) R2=R4

(RF207) Case 2: for a given (a) _________ compound (R1-)(R2-)C-C(sub. 'n-1')(-R3)(-R4), where 'n' is the number of carbon atoms in the compound, R1≠R2, (b)________, [R1,R2,R3, & R4 are all (c)________] and R1 & R3 are on opposite sides of the (d) r________ ________, it is the 'cis-' isomer of the compound and is referred to as ''cis-'+[IUPAC name of the (a) _________ compound]' when (e) ________, or (f) ________3.

(a) cyclic (b) R3≠R4 (c) groups of atoms (d) reference plane (e) R1=R4 (f) R2=R3

For (a)__________ compounds, there is (b)__________ rotation about (c)__________ bonds. They can form cis-trans (d)__________

(a) cyclic (b) no free (c) single (d) & E/Z isomerism

'(R1-)(R2-)C-C(sub. 'n-1')(-R3)(-R4)' is a compound with a (a) ______ r______, but is not a (b) ______ isomer when (c) ________ or ________, where R1 and R3 are on (d) o________ sides of the (e) ________ p________, but can be a (f) ________ or ________ depending on the (g) ________ of R1,R2,R3, and R4, which are all (h) g________ ________ of a________.

(a) cyclic ring (b) 'cis-trans & E/Z' (c) R1=R2 or R3=R4 (d) opposite (e) reference plane (f) structural isomer or stereoisomer (g) nature (h) general groups of atoms

Anti-aromatic compounds are __________

(a) cyclic, (b) planar, (c) have an even number of 'pi'-cloud electron pairs, (d) and generally unstable

Aromatic compounds are __________

(a) cyclic, (b) planar, (c) have an odd number of 'pi' cloud electrons pairs, (d) and are generally stable

The (a) ________ of ________ / (IHD) can be used to determine from a given (b) ________ ________ the (c) ________ of ________ or (d) ________ ________ in the same given (e) ________.

(a) degree of unsaturation (b) molecular formula (c) number of rings (d) multiple bonds (e) compound

To draw different (a) ________ of the (b) s_______ c________ c________, swap the (c) ________ of ________ [(d) d________ or ________] of the (e) _____ ______ drawn with another (c) ________ of ________ [(d) d________ or ________] at (h) s_____ _____ _____ a_____ (i) c_______ c________. Note: (j) s_______ formulae are often (k) u______ to show the (l) c________ ________ of the compound when drawing (a) ________:

(a) diastereomers (b) same (c) chiral compound (d) type of line (e) dashed, normal, or wedged (f) 1st diastereomer (g) another (h) some but not all (i) carbons (j) skeletal (k) used (l) carbon backbone

'cis-trans & E/Z' isomers can have (a) d________ (b) p_______ p________ depending on the (c) ________ of the bonded (d) ________ of ________ on (e) ________, the shape, and (f) ________ of a given compound. Generally, the (g) ________ isomer of a given compound has a higher (h) ________ ________ and lower (i) ________ than the corresponding 'trans-' isomer of the (j) ________ compound as the overall (k) ________ of the 'cis-' isomer is less (l) ________ than the corresponding 'trans-' isomer, leading to (m) _______ (n) ________ ______-______ ________ for the 'cis-' isomer than the latter. Thus, the (b) p_______ p_______ [like boiling points, melting points, and (o) _______ ] are reported (p) _______ for each 'cis-trans & E/Z' isomer of a given compound.

(a) different (b) physical properties (c) influence (d) groups of atoms (e) polarity (f) symmetry (g) 'cis-' (h) boiling point (i) volatility (j) same (k) shape (l) symmetric (m) greater (n) permanent dipole-dipole interactions (o) solubility (p) separately

To draw (a) d________ enantiomers of the (b) s________ chiral compound, start with drawing the (c) _____ _____. The (d) ________ ________ of the (c) ________ is the (e) _____ _____ of ________. Use (f) ____ (g) _______ lines ('------'), (h) _____ ______ lines, and (f) ____ (i) _____ _____ line (---<<<) (j) ________ when drawing (k) ________ of the (l) t_____ d_______ t______ of enantiomers as (m) s_______n:

(a) different (b) same (c) 1st enantiomer (d) mirror image (e) 2nd type of enantiomer (f) one (g) dashed (h) two normal (i) solid wedge (j) respectively (k) each (l) two different types (m) shown

'(R1-)(R2-)C=C(-R3)(-R4)' has a (a) ______ b______d, but is not a (b) ________ isomer when (c) ________ or ________, where R1 and R3 are on (d) o________ sides of the (e) ________ p________, but may be a (f) ________ or ________ depending on the (g) ________ of R1,R2,R3, and R4, which are all (h) g________ ________ of a________.

(a) double bond (b) 'cis-trans & E/Z' (c) R1=R2 or R3=R4 (d) opposite (e) reference plane (f) structural isomer or stereoisomer (g) nature (h) general groups of atoms

(RF200) There are only 2 circumstances when cis-trans & E/Z isomerism occurs: 1-for (a)___________ having different (b) ___________ bonded on (c) ___________ side of the (d) ___________ 2-for (e) ___________ compounds that have (f) ___________ different (b) ___________ bonded to the (g)___________, on (h) ___________ carbon atoms.

(a) double-bonded compounds (b) groups of atoms (c) at least 1 (d) double bond (e) cyclic (f) at least 2 (g) main ring (h) different

The (a) _________ groups (b) _________ that help determine 'cis-trans' isomerism (c) d_______ _______ ________ have to be on (d) _________ carbon atoms: it is their (e) _________ relative to the plane of (f) _________ that helps (g) _________ the 'cis-trans' isomer, provided that they are not critically (h) _________ to the (i) ______ (j) ______ atom.

(a) equivalent (b) of atoms (c) do not necessarily (d) adjacent (e) position (f) the ring (g) define (h) bonded (i) same (j) carbon

(RF217) Such priority rules consist of (a) e_______ e_______ of the (b) ________ bonded to (c) ________ ________ of the (d) ________ bond, assigning (e) ________ ________ to the atom with the (f) ________ 'Z' [(g)_______] and (h) r_______ the (i) ________ process with the (j) o_______ ______ of the (d)________ bond. If both (b) ________ are the (i)________, apply the (i)________ rule to the next (k) ________ group of (l) ________ (if there are no such (k) ________ groups/atoms and the (m) ________ bonded to (c) ________ of the (d) _______ bond have the same 'Z' / are the same, the compound being examined c________ f________ ________) until one of the (o) ________ bonded to the (i) ________ side of the (d) ________ bond can be distinguished to be of (e) ________ (Rules 1 and 2). These rules can be applied to (p) ________ as well, where each of the (q) t_____ r_______t p_______ on the (r) ________ is examined for the (s) ________ of ________of (e) ________.

(a) examining each (b) atoms (c) one side (d) double (e) higher priority (f) higher (g) mass number (h) repeating (i) same (j) other side (k) consecutive (l) each atom (m) two atoms (n) cannot form 'cis-trans & E/Z isomerism' (o) two initial atoms (p) cyclic rings (q) two relevant points (r) cyclic ring (s) group of atoms

The (a) ________ ________ substituents of a (b) ________ compound can be arranged in two (d) _______ _______ c_______, which are (e) ________ (f) ________ i________ of (g) ________ other. This entire phenomena is referred to as (h) ________ i_______.

(a) four different (b) substituents (c) chiral (d) different (e) 3D configurations (f) non-superimposable (g) mirror images (h) each (i) optical isomerism

Primary (a)________________ has the C attached to the Cl/Br with (b)_______ C atom attached.

(a) halogenoalkane (b)only one/one

Unlike diastereomers, enantiomers have (a)________ physical and chemical properties with the exceptions of their (1) (b)________ on the (c)________ of oscillation of (d)________ and (2) their (e)________ properties in (f)________ environments

(a) identical (b) effect (c) plane (d) plane-polarized light (e) chemical (f) chiral environments

When calculating the (a) ________ (IHD) from a molecular formula or (b) ________, count (c) e________ _______ in the compound as (d) _____ _____ atom, ignore atoms of (e) ________ e________ [like (f) o________], and remember to (g) ________ (d) ______ ______ every time there is an (h) ________ of G________ [e.g., (i) ________, phosphorus] in the compound, before finally dividing by (j) ______. The IHD is based on the general (k) ________ (l) '________'.

(a) index of hydrogen deficiency (b) otherwise (c) every halogen (d) 1 hydrogen (e) Group 16 elements (f) oxygen (g) subtract (h) atom of Group 15 (i) nitrogen (j) two (k) formula (l) CnH2n+2

The (a) ________ t________ of a given (b) ________ s________m indicates the (c) ________ ________ of ________ in the displayed (d) ________ of ________.

(a) integrated trace (b) 1HMNR spectrum (c) relative number of protons (d) number of environments

(RF207) In these cases, different 'cis-trans & E/Z' (a) ___________ of the same compound can be (b) ___________ between by (c) ___________ the (d) ___________ of such key (e) ___________ with respect to a ___________.

(a) isomers (b) distinguished (c) describing (d) position (e) groups of atoms (f) reference plane

Stereoisomerism: compounds with the same (a)__________ formula and (b) __________, but with different (c)__________ of (d)_________

(a) molecular (b) bond multiplicity (c) spatial arrangements (d) atoms

(RF217) Utilize these principles / rules alongside the given (a) ________ to (b) ________ (c) ______ structures of (d) ________ exhibiting (e) ________ accordingly [E/Z isomerism is a more (f) ________ (g) e________ of the (h) ________].

(a) molecular formula (b) draw (c) 3D (d) compounds (e) cis-trans and/or E/Z isomerism (f) comprehensive (g) extension (g) cis-trans naming system

The (a) ________ ________: if a proton has n protons as nearest (b)___________, its NMR peak is split into a group of (c)_______ peaks.

(a) multiplicity rule (b) neighbors (c) (n+1)

(RF324) When (a) ______, the (b) ________ is a 'singlet'; when n = 1, the (b) ________ is a (c) ________; when n = 2, the (b) ________ is a (d) ________; when n = 3, the (b) ________ is a (e) ________, and when n = (f) ________, the splitting pattern is a (g) ________ / (h) ________ or likewise progressively

(a) n = 0 (b) splitting pattern (c) doublet (d) triplet (e) quartet (f) 5 or more (g) multiplet (h) quintet

In order to compare the (a) ________ a_______ of (b) ________ solutions, the (c) ________ c________, the (d) ________ of the (e) ________ u________, and the ________ ________ ________ must all be kept c_______.

(a) optical activity (b) different (c) solution concentration (d) wavelength (e) light used (f) sample path length (g) constant

Diastereomers: (a) __________s of the same compound that have (b) __________ __________ at (c) s__________ (d) c__________ c__________ & are (e) ________ __________ i_________ of (f) __________ __________r.

(a) optical isomers (b) opposite configurations (c) some but not all (d) chiral carbons (e) not mirror images (f) each other

The '-O-H' bond is (a) _______ and (b) i_______ the (c) _______ of alcohols. However, alcohol (c) _______ (d) d_______ as you move along the chain and (e) _______ _______ as progressively (f) _______ _______ of the alcohol are (g) ______-______.

(a) polar (b) increases (c) solubility (d) decreases (e) homologous series (f) larger proportions (g) non-polar

(RF266) A (a) ________ converts a (b) b________ of (c) ________ light to (d) p________ ________

(a) polarizer (b) beam (c) ordinary (d) plane-polarized

After Rules 1 and 2, the (a) p________ of the previously-assigned (b) ________ (c) ________ p_______ (d) ________ of ______ on (e) e________ s________ of the (e) ________ bond / (f) ________ ________ are compared: -If the (b) ________ (c) ________ p_______ (g) g______ chosen [1 from each side of the (e) ________ bond / (f) ________] are on the (h) ________ ________ of the (i) r________ p_______, then the given isomer is a (j) '____-[n______ of ________]' -If the (b) ________ (c) ________ p_______ (g) g______ chosen [1 from each side of the (e) ________ bond / (f) ________]) are on (k) ________ sides of the (i) r_______ p_______, then the given (l) ________ is 'E-[name of compound]'

(a) positions (b) 2 (c) highest priority (d) groups of atoms (e) double (f) cyclic ring (g) groups (h) same side (i) reference plane (j) 'Z-[name of compound]' (k) different (l) isomer

(a)__________ solvents contain-OH or -NH and are able to form (b)___________ bonds

(a) protic (b) hydrogen

(RF255) When a (a) ________ mixture is reacted with a (b) ________ enantiomer of (c) ________ (d) ________ compound, the two (e) ________ components of the mixture (the '(+)' and '(-)' enantiomers) (f) r________ to produce (g) ________ products. These products have (h) ________ chemical and physical properties and so can be (i) ________ from each other relatively easily. This process is, thus, a means of (j) ________.

(a) racemic (b) single (c) another (d) chiral (e) initial (f) react (g) different (h) distinct (i) separated (j) resolution

A (a) ________ ________ [additionally called a (b) ________] is a mixture that contains (c) e________ amounts of the two (d) ________ enantiomers of a given (e) ________ compound and, subsequently, has no (f) ________ ________ on the (g) ________ of oscillation of (h) p________ ________. Thus, (i) ________s are said to be (j) o________ ________

(a) racemic mixture (b) racemate (c) equal (d) different (e) chiral (f) overall effect (g) plane (h) plane-polarized light (i) racemic mixtures (j) optically inactive

Relative rate of reactivity, in descending order of reactivity rate, for analogous halogenoalkanes undergoing nucleophilic substitution, in general, for a polar protic environment, whilst keeping other factors constant: (e) _______ [(f) _____ mechanism _____] > Secondary carbon [(g) __________] > (h) ______ carbon [(i) _____ mechanism _____]

(a) reactivity rate (b) nucleophilic substitution (c) polar protic (d) constant (e) tertiary (f) SN1 mechanism only (g) SN1 or SN2 mechanism (h) primary (i) SN1 mechanism only

The (a) ________ plane of a given (b) c_______c r______g (c) p______s ________ through the (b) c_______c r______g

(a) reference (b) cyclic ring (c) passes horizontally

Non-superimposable mirror images are (a) _______ about a (b) f_______, _______ plane that do not (c) ______ ______ with (d) ______ other when (e) a________ on the (f) ________ (g) ________ and (h) v________ (i) p________ as each other.

(a) reflections (b) flat, upright (c) line up (d) each (e) aligned (f) same (g) horizontal (h) vertical (i) planes

Cycloalkanes consist of a (a) ________ of (b) ________ atoms that (c) ________ ________ (d) a________ the (e) ________ bonds of key carbons.

(a) ring (b) carbon (c) restricts rotation (d) about (e) 'sigma'

(R189) I.e., the 'cis-' isomer of any given compound has the (a) ________ (b) ________ on the (a) ________ side of the double bond / (c) ________, whilst the 'trans-' isomer of any given compound has the (a) ________ (b) ________ across the (d) _________

(a) same (b) groups of atoms (c) cyclic ring (d) reference plane

molecular formula

(a) shows the exact number of atoms of each type (b) in a given compound

empirical formula

(a) shows the simplest whole-number ratio of atoms (b) in a compound

The manufacture of a specific (a) ________ enantiomer of a given chiral compound using a (b) c________ ________ is called (c) a________ ________

(a) single (b) chiral catalyst (c) asymmetric synthesis

(R) The nature of the carbon (a) _______n affects the rate of (b) _______ _______. A (c) _______ i_______ in the (d) _______ _______m is normally (e) m_______ s_______ than an analogous (f) _______ _______ in the (g) _______ _______. Thus, (d) _______ _______ reactions are generally faster than comparable (g) _______ _______ reactions, provided the (h) _______ _______ is sufficiently (i) _______ _______ and more.

(a) skeleton (b) nucleophilic substitution (c) carbocation intermediate (d) SN1 mechanism (e) more stable (f) transition state (g) SN2 mechanism (h) surrounding environment (i) polar protic

The (a)__________ of a compound does (b)__________ determine its (c)__________ / whether the compound is aromatic or (d) __________

(a) smell (b) not necessarily (c) aromaticity (d) not

A sample of (a) ________ that notably (b) ________ the (c) ________ of oscillation of (d) p________-________ ________ is called (e) ________ ________ and may contain (f) ________ enantiomers of a given chiral compound

(a) solution (b) rotates (c) plane (d) plane-polarized light (e) optically active (f) identical

What does SN1 stand for and why?

(a) unimolecular nucleophilic substitution (b) The reaction rate depends exclusively on the leaving group.

Esters are (a)___________ and (b)________ and have (c)____ boiling points. Esters of (d)__________ molecular size have a (e)______ boiling point and have less (f)___________.

(a) volatile (c) smelly (d) low (e) larger (f) higher (g) volatility

Only one isomer exists for compounds such as (a)____________________ As it is (b)_______________ all adjacent positions in the ring are (c)_______

(a)1,2 dibromobenzene. (b)symmetrical (c)equal

The second stage of electrophilic substitution for nitration of Benzene starts with a collision between a (a)____________ molecule and the (b)_______________.

(a)Benzene (b)electrophile

The radicals then react with methane molecules. In the process, a methyl radical is produced. The methyl radical reacts quickly with a Cl₂ molecule. eg. Cl∙(g)+(a)______→(UV)→(b)______+HCl(g) or (c)________+Cl₂(g)→(d)___→CH₃Cl(g)+(e)_______This is a chain reaction

(a)CH₄(g) (b)CH₃∙(g (c)CH₃∙(g) (d)(UV) (e)Cl∙(g)

A tertiary halogenoalkane has the (a)______ attached to the Cl with (b)_______ other C atoms attached

(a)Carbon(C) (b)three

(a)__________________and (b)___________ can produce electronic transitions and give information about the (c)____________________________ within the atom or molecule.

(a)Visible light (b)UV light (c)electronic energy levels

Benzene resists (a)_________ reactions: because it would involve disrupting the entire delocalized electron cloud so is (b)_________ not favored as the product formed would be (c)_______ stable.

(a)addition (b)energetically (c)less

(a)________ are more reactive than (b)_________ because C=C bonds have bond enthalpy that is less than twice the average value of that of C-C bonds.

(a)alkenes (b)alkanes

When a covalent bond (a)________ by (b)_______ the shared pair of electrons between the two products. It produces two free radicals, each with an (c)__________ electron. X:X→X°+X°. It is a type of (d)___________ fission

(a)breaks (b)splitting (c)unpaired (d)homolytic fission

An electron-rich species which is therefore attracted to parts of the molecule which are electron (a)____________,Have _____ __________ of electrons and may also have a negative charge. They are called ___________

(a)deficient (b)lone pairs (c)Nucleophiles.

A primary amine is when the NH₂ group is on the (a)_________of a chain, the naming goes the stem goes first followed by amine. A secondary amine is when the NH₂ group is a (b)____________on the chain, the naming goes the (c)_________, then (d)_________, then the stem. A tertiary amine is when there is a methyl group in the compound, the naming goes the number, then amino, then methyl, then the stem.

(a)end (b)branch (c)number (d)amino

The rate of nucleophilic substitution reactions in halogenoalkanes is (a)______________ with tertiary halogenoalkanes and (b) with primary halogenoalkanes.

(a)fastest (b)slowest

Alcohols have (a)______________ boiling points than ethers and are more soluble in water because alcohol molecules can form hydrogen bonds to each other and also to water molecules. Ethers have no (b)______________ ______bonded to oxygen atoms and so cannot form hydrogen bonds.

(a)higher (b)hydrogen atoms

TMS(Tetramethylsilane) is used as a reference in the NMR spectroscopy and is advantageous because: -The (a)___________ nuclei are all in the (b)____ environment and (c)______signal is recorded. -(d)_________has a lower electronegativity than carbon so TMS absorbs radio waves in a different region from that absorbed by hydrogen nuclei attached only to carbon and this ensures that the standard signal does not (e)__________with any signals under investigation. -Additionally, TMS is chemically (f)________ and is (g)__________ in most organic solvents. -It can easily be removed from the sample as it has (h)______ boiling point.

(a)hydrogen (b)same (c)signal (d)Silicon (e)overlap (f)inert (g)soluble (h)low

As the number of carbon atoms in a molecule in any homologous series increases, the boiling point (a)________________ The boiling point of straight-chain alkanes (b)________________when a methylene (-CH2-) group is added, because the strength of the London forces between molecules increases as the relative molecular mass (number of electrons in the molecule) of the alkanes (c)______________. A similar trend is seen in the boiling points of other homologous series.

(a)increases (b)increases (c)increases

Common reducing agents are (a)____________________ (a)___________) and _(b)____________((b)__________). (c)_______________ is the stronger reducing agent and can be used to reduce carboxylic acids, aldehydes and ketones but (d)__________ is only strong enough to reduce aldehydes and ketones. However, (e)_______________ is much easier to use than(f)______________ and so is usually preferred for the reduction of aldehydes and ketones.

(a)lithium aluminium hydride,(LiAlH4) (b)Sodium borohydride(NaBH4) (c)LiAlH4 (d)NaBH4 (e)NaBH4 (f)LiAlH4

By identifying the peaks from the spectrum, we can identify the (a)______ or (b)__________ of (c)__________ by referring to section 28 of the data booklet.

(a)loss/presence (b)presence/loss (c)specific ions

The x-axis in the mass spectrometry graph shows the (a)_____________ and the y-axis shows the relative abundance in terms of the number of (b)__________. The peak on the right-most side of the graph corresponds to the (c)_______________ of the parent ion. The ratio of the molecular formula can be deduced by dividing the (c)________________ of the parent ion with that if the (d)_________________

(a)mass/charge (b)peaks (c)relative mass (d)empirical formula

SN1 is (a)__________ favourable for tertiary halogenoalkanes because of the (b)_________ of the intermediate carbocation. Methyl groups (and alkyl groups in general) have an electron-releasing effect (also called a positive inductive effect) so that they are able to stabilise a (c)___________ charged carbon atom to which they are bonded.

(a)more (b)stability (c)positively

The double bond has a high electron density and forms a (a)___________ region The pi bond forms an (b)__________ p orbital - not as strong as twice a single bond (c)___________ reactions mean adding something to the compound so (d)_________ adds across the double bond.

(a)negative (b)unhybridized (c)Addition (d)water

gives the minimum information to describe the molecule (a)_______________ Eg. Propane C3H8, would be CH3CH2CH3. They are examples of (b) ___________________ formulas.

(a)non-ambiguously (b)condensed structural

The orange to green color change is only seen if an (a)___________ occurs, not seen in (b)___________ alcohols; it is seen consistently throughout the oxidation of primary alcohols to aldehydes, aldehydes to carboxylic acids, the oxidation of primary alcohols to aldehydes to carboxylic acids, and the oxidation of secondary alcohols to ketones.

(a)oxidation (b)tertiary

Benzene has a delocalized (a)_____ system, containing six electrons and the system represents a region of (b)_________ electron density and therefore Benzene is susceptible to attack by electrophiles.

(a)pi (b)high

*The two enantiomers of a chiral compound rotate (a)___________________ light in (b)__________ and _(c)___________ directions.

(a)plane-polarised (b)equal (c)opposite

A secondary carbocation is more stable than a primary carbocation because of the electron-releasing effect of alkyl groups ,also called a (a)____________________Because the secondary carbocation is more stable, it is (b)__________ likely to be formed.

(a)positive inductive effect (b)more

A (a)_____________ carbocation has one carbon atom attached to the C with the (b)___________ charge. • A secondary carbocation has (c)________ carbon atoms attached to the C with the_(d)____________ charge

(a)primary (b)positive (c)two (d)positive

SN2 reactions are favoured by (a)________, (b)_______ solvents

(a)protic (b)polar

Splitting of the signal of a particular group of protons is due to the (a)_________ on (b)_____________ atoms.

(a)protons (b)adjacent (carbon)

Energy in the (a)_______________ range of the electromagnetic spectrum can be used to cause a hydrogen nucleus to change its (b)_____________ relative to the applied magnetic field.

(a)radio frequency (b)orientation

''Rules' for spin-spin coupling •Protons on the (a)______ atom do not split each other -they are chemically (b)_______ and behave as a group. •Splitting generally only occurs with protons on (c)___________ atoms •Protons attached to (d)_________ atoms do not usually show or cause splitting - this is because the protons exchange with each other and with the solvent and experience an 'average' environment.

(a)same (b)equivalent (c)adjacent (d)oxygen

The C attached to the Br has two other C atoms attached. It is a type of (a)_______________(b)_________________.

(a)secondary (b) halogenoalkane

The carbons of alkanes are all(a)____ hybridized and are stable. They are saturated with strong, non-polar C-C and C-H bonds. Only react in the presence of (b)__________ strong enough to break bonds. Alkanes are(c)___________ under most conditions - can be stored, transported, compressed safely. Undergo (d)_______________ reactions.

(a)sp3 (b)energy source (c)stable (d)free-radical substitution

Infrared radiation is absorbed by certain bonds causing them to (a)_______ or (b)_____________This gives information about the (c)__________ in a molecule.

(a)stretch/bend (b)bend/stretch (c)bonds

Halogenation of alkanes is a type of (a)_____________________ reaction whereas halogenation of alkenes is a type of (b)____________________ reaction.

(a)substitution (b)addition

Benzene can partake in (a)_____________ reactions: because (a)______________ preserves the ring structure of Benzene and is (b)_________ energetically favored.

(a)substitution (b)more

Cl∙+Cl∙→(UV)→CL₂ is an example of (a)______________ in the (b)_____________ substitution mechanism.

(a)termination (b)free-radical

To determine the ratio between the number of hydrogen atoms(protons) in each environment measure the (a)_______________ height of each step in the (b)_____________________ using a ruler and find the ratio between the heights - this is the same as the ratio between the numbers of (c)______________ in each environment.

(a)vertical (b)integration trace (c)protons

The bromine water changes from orange to colorless, indicating that it is an (a)alkane (b)alkene (c)alkyl (d)alcohol

(b)alkene

An alkene reacts with steam to form an alcohol, the type of reaction that occurs is: (a)an electrophilic substitution reaction (b)nucleophilic addition reaction (c)electrophilic addition reaction (d)free-radical substitution reaction

(c)electrophilic addition reaction

Products of incomplete combustion are* (a)Carbon dioxide, water and soot (b)Oxygen, Carbon dioxide and water (c)Oxygen, carbon monoxide and water (d)Carbon monoxide and water

(d)Carbon monoxide and water. May also form soot.

Properties of structural isomers

- have unique physical and chemical properties. -Number increases with the size of the chain. -Structural isomers can be split again into three main subgroups: Chain, positional and functional isomers.

High resolution H^1NMR spectrum

-Allows us to determine splitting pattern -splitting=n+1, where n is the number of Hs on an adjacent carbon Quartet:4lines together Triplet:3lines together Singlet:one line

*Alkenes to Alkanes Addition reaction with hydrogen(Hydrogenation)

-An alkene reacts with hydrogen to form an alkane -The double C=C bond is broken and converted to a C-C single bond. The H2 then breaks open and attaches itself as two individual H atoms to the carbon in the question *catalyst: Finely divided nickel -Electrophilic addition.

*Alkenes to alcohols Addition reaction with water(Hydration)

-An alkene reacts with steam to form an alcohol -The double C=C bond is broken and is converted into a C-C single bond -H2O then breaks open and attaches itself as H and OH to the carbon atoms that are now open *Reaction conditions; -Heat with H2O *catalyst: concentrated H2SO4

What are the conditions for polymerisation reaction to occur?

-High temperature and pressure -A suitable catalyst:(for example,Al of Ti)

How can you distinguish between alkanes and alkenes?

-One mode is the bromine water test; Upon shaking bromine water with each -Alkanes do not decolorize bromine water in the absence of UV light and relatively cold conditions, whereas ... -Alkenes decolorize bromine water under normal conditions

Properties of homologous series

-Share the same general formula. -contains the same functional group. -successive compounds differ by a CH2 group in each family. -Have similar chemical properties. -Gradation in physical properties.

Naming ether (P1)

-The common method: the two alkyl groups (i.e. carbon chains) are alphabetized in the name, - the officially sanctioned IUPAC method (as an alkoxyalkane) wherein the smaller carbon chain and the O-atom are collectively named as an alkoxy branch (e.g. -O-CH3 is methoxy) on the larger carbon chain.

The oxidation of any primary alcohol is a two-step process that first produces an ________ which is then further oxidized to a ______________ _______

-aldehyde -carboxylic acid

Suffix in IUPAC name for alkane

-ane

Suffix in IUPAC name for alcohol

-anol

What is the IHD of C6H12Br2?

-for 6 C-atoms, 2(6)+2 = 14 H-atoms -there are 12 H-atoms and 2 halogens = 14 "H-atoms" IHD = 0

The oxidation of any secondary alcohol is a ______ -step process that produces a _______.

-one -ketone

Suffix in IUPAC name for ethers

-oxyalkane

Other polymer names for each.

-polyethene/polythene -Polyvinylchloride/chloroethene -tetrafluoroethene respectively.

Name three common addition polymers.

-polyethylene -PVC -Teflon

When reducing carboxylic acids to primary alcohols, use a very strong ________ ________ like _______

-reducing agent -LiAlH4

What are the conditions for the esterification reactions?

-reversible reaction -catalyst:concentrated H2SO4

Counting the hydrogen environments

1) Think like a hydrogen atom, how many different points are there in terms of perspective. 2) Count up the number of H environments ->number of peaks on a low resolution spectrum.

Steps of Electrophilic substitution

1. A pair of electrons from the π -system attacks the NO2+ electrophile forming a coordinate bond and destroying the delocalization 2. The HSO4− ion acts as a base, pulling off a hydrogen atom and reforming sulfuric acid 3. The C−H bond breaks and the two electrons reform the delocalized π -system 4. The C−H bond breaks and the two electrons reform the delocalized π -system.

Naming Alkanes

1. Find the longest continuous carbon chain. 2. Choose the prefix corresponding to the number of carbon atoms in the longest continuous carbon chain 3. Add the ending 'ane' to indicate an alkane. 4. Look for substituent groups (alkyl groups). 5.Number the positions of the substituent groups using the combination that has the lowest individual numbers (not the sum). 6. Choose a prefix to indicate the number of each substituent present. 7.Arrange the names of the substituent groups in alphabetical order (ignoring the prefix used in step 6).

When naming organic compounds remember to

1. Identify the longest backbone of carbon atoms 2. Side chains are numbered with the lowest number

Additional rules when naming organic compounds are:

1. Numbers are separated by a coma 2. Numbers and names are separated by a dash 3. Words/names have no spaces between them 4. If there is more than one side branch or group, then they are listen alphabetically

Primary, secondary and tertiary halogenoalkanes

1. Primary: The C attached to the Cl has only one C atom attached - one C attached='primary'. 2. Secondary:The C attached to the Br has two other C atoms attached - two Cs attached='secondary'. 3. Tertiary: The C attached to the Cl has three other C atoms attached - three Cs attached='tertiary.

Why are members of the alkane series unreactive?

1. The relative bond enthalpies between C-C and C-H bonds. Strong bonds =large amount of energy required to break. 2. The polarity of the C-C and C-H bonds. C-C non-polar covalent tends to be left alone by other molecules. C-H polar covalent, however C can leave H for another halogen.

Incomplete combustion reaction of alkanes(CH4 and C3H8)

2CH4+3O2→2CO+4H2O or CH4+O2→C+H2O C3H8(g) + 41⁄2 O2(g) 2 CO2(g) + CO(g) + 4 H2O(l) C3H8(g) + 31⁄2 O2(g) 3 CO(g) + 4 H2O(l) C3H8(g) + 3 O2(g) 2 CO(g) + C(s) + 4 H2O(l)

Complete combustion reaction of alkanes(CH4 and C3H8)

2CH4+4O2→2CO2+4H2O C3H8(g) + 5 O2(g) 3 CO2(g) + 4 H2O(l)

General Eq^n for the oxidation of an aldehyde to a carboxylic acid using acidified potassium dichromate (VI):

2RCHO + (Cr2O7)^2− + 8H^+ → 3RCOOH + 2Cr^3+ + 4H2O

General Eq^n for the oxidation of a given primary alcohol → its corresponding aldehyde with acidified K2Cr2O7:

3HRCHOH + (Cr2O7)^-2 + 8H^+ → 3RCHO + 2Cr^3+ + 7H2O, where 'R' is a general group of atoms

General Eq^n for the oxidation of a secondary alcohol to a ketone using acidified potassium dichromate (VI):

3R'RCHOH + (Cr2O7)^2- + 8H^+ → 3R'COR + 2Cr^3+ + 7H2O

General Eq^n for the oxidation of a primary alcohol to a carboxylic acid using acidified potassium dichromate (VI):

3RCH2OH + 2(Cr2O7)^2- + 16H^+ →3RCOOH + 4Cr^3+ + 11H2O

General Eq^n for the oxidation of a given primary alcohol → its corresponding aldehyde with acidified KMnO4:

5HRCHOH + 2(MnO4)^- + 6H^+ → 5RCHO + 2Mn^2+ + 8H2O, where 'R' is a general group of atoms

General Eq^n for the oxidation of a given secondary alcohol → its corresponding ketone with acidified KMnO4:

5R'RCHOH + 2(MnO4)^- + 6H^+ → 5R'COR + 2Mn^2+ + 8H2O, where 'R' is a general group of atoms

General Eq^n for the oxidation of a given aldehyde → its corresponding carboxylic acid with acidified KMnO4:

5RCHO + 2(MnO4)^- + 6H^+ → 5RCOOH + 2Mn^2+ + 3H2O, where 'R' is a general group of atoms

General Eq^n for the oxidation of a given primary alcohol → its corresponding carboxylic acid with acidified KMnO4:

5RHCHOH + 4(MnO4)^- + 12H^+ → 5RCOOH + 4Mn^2+ + 11H2O, where 'R' is a general group of atoms

Homologous series

A series of compounds of similar structure in which each member differs from the next by a common repeating unit, CH2 . The members of the series are called homologues.

Which of the following contribute significantly to the low reactivity of alkanes? I. The relatively strong C-H bond II. The very low polarity / zero polarity of the C-H and C-C bonds respectively III. The tetrahedral shape of the molecules A. I and II only B. I and III only C. II and III only D. I, II and III

A. I and II only

How many structural isomers are there with the molecular formula C4H10? A.2 B.3 C.4 D.5

A.2

What does the peak at 15 with the peak of the parent ion being 60 infer?

According to the data booklet, presence of CH3+ and loss of COOH from molecule(60-45)

Alcohol reactions

Alcohols undergo nucleophilic substitution reactions with acids (esterification / condensation) and some undergo oxidation reactions

Alcohol complete combustion reactions

Alcohols will combust in the presence of a strong oxidizing agent such as oxygen gas, O2: methane: CH4(g) + 2 O2(g) CO2(g) + 2 H2O(l) methanol: CH3OH(l) + 3/2 O2(g) CO2(g) + 2 H2O(l)

Are esters aliphatics, arenes, or aromatic compounds?

Aliphatics

Arrange the following in terms of boiling point in order of increasing boiling point, using the '>' symbol as needed: halogenoalkanes, aldehydes, ketones, alkanes, carboxylic acids, and alcohols

Alkanes > Halogenoalkanes > Aldehydes > Ketones > Alcohols > Carboxylic Acids

Arrange the following in terms of strength of intermolecular forces of attraction in ascending order, using the '>' symbol as needed: halogenoalkanes, aldehydes, ketones, alkanes, carboxylic acids, and alcohols

Alkanes > Halogenoalkanes > Aldehydes > Ketones > Alcohols > Carboxylic Acids

Arrange the following in terms of volatility in order of decreasing volatility, using the '>' symbol as needed: halogenoalkanes, aldehydes, ketones, alkanes, carboxylic acids, and alcohols

Alkanes > halogenoalkanes > aldehydes > ketones > alcohols > carboxylic acids

Distinguishing alkane and alkenes.

Alkene: bromine water - orange to colourless Alkane: bromine water - no colour change

What reaction does alkenes undergo?

Alkenes are more reactive than alkanes and undergo addition reactions with water to produce alcohols.

*Alkenes to Halogenoalkanes Addition reactions with Hydrogen Halides(Hydrohalogenation)

Alkenes react with hydrogen halides, such as hydrogen bromide, by *bubbling the alkene through a concentrated solution of the hydrogen halide at 100 °C. -Electrophilic addition. *Reaction conditions: -In solution at room temperature: occurs rapidly.

Evidence for Bond length

All C-C bond lengths in Benzene are equal and intermediate in length between single and double bonds. From X-ray crystallography.

Step 5 for naming compounds

All other groups are then named using the PREFIX form, being arranged in alphabetical order.

Electrophile

An atom (or group of atoms) that is attracted to an electron-rich centre or atom, where it accepts a pair of electrons to form a new covalent bond.

_________ are a class of compounds that are derived from benzene C₆H₆. They form a class of compounds known as aromatics, which have properties distinct from other organic compounds.

Arenes

What is the functional group for an arene?

Arenes contain the phenyl funtional group C₆H₅.

Which products are most likely to be formed if excess butane is burned in a limited supply of air? A. hydrogen and carbon B. water and carbon monoxide C. hydrogen and carbon dioxide D. hydrogen and carbon monoxide

B. water and carbon monoxide

What is Benzene's IHD?

Benzene (C6H6) has an IHD of 4 because it contains one ring and the equivalent of three double bonds.

Thermochemical evidence

Benzene is more stable than predicted from the Kekulé structure by ~152kJ/mol

Type of reactivity-evidence

Benzene resists addition reactions: because it would involve disrupting the entire delocalized electron cloud so is energetically not favored as the product formed would be less stable. Benzene can partake in substitution reactions: because substitution preserves the ring structure of Benzene and is more energetically favored.

Naming aldehydes

CHO is always at the end, so no numbers. Simply write stem and add -anal-

A compound has the molecular formula C7H8. What is its IHD? What are three options for structural components of the molecule that would cause it to have this IHD?

CNH2N+2 = C7H2x7+2 = C7H16 but this compound is C7H8 IHD = ((2×7+2) - (8))/2 = (16-8)/2 = 8/2 = 4 (i) The compound could have 2 triple bonds. (ii) The compound could contain 2 rings and have 2 double bonds. (iii) The compound could have 1 ring and 3 double bonds. Note that this is what resonance structures of benzene have. As benzene rings are fairly common in organic chemistry, an IHD ≥ 4 often indicates the presence of a benzene ring in the compound.

What is the functional group for an ester?

COO (both an aldehyde and ketone)

The functional group for carboxylic acids is ________

COOH

This homologous series has a COOH bond at the end of the carbon chain.

Carboxylic acid

Esters are isomers of __________ ______

Carboxylic acids.

The reaction between an alkene and water is called __________ __________ It is used in the industrial production of ethanol, an important solvent

Catalytic hydration.

General formula for aldehydes

Cn(H2n+1)CHO

General Formula for Alkenes

CnH2n

General formula for alcohols

CnH2n+1OH

General Formula for Alkanes

CnH2n+2

General Formula for Alkynes

CnH2n-2

Low resolution H^1NMR spectrum

Compare peaks and their shift values against the data booklet. Integration trace(dotted lines):tells us the ratio of the areas under the graph and are is the number of hydrogen atoms in the H environment.

The oxidation state changes of Cr throughout when using K2Cr2)7 is

Cr(VI) to Cr(III)

General Eq^n for the incomplete combustion of alcohols:

CxH(y-1)OH + ((y+2x-2)/4)O2 → xCO + (y/2)H2O, where 'x' and 'y' are the number of moles of carbon atoms and hydrogen atoms respectively

General equation for the complete combustion of alcohols

CxH(y-1)OH + [(y+4x-2)/4]O2 → XCO2 + (y/2)H2O, where 'x' and 'y' are the number of moles of carbon atoms and hydrogen atoms respectively

General Eq^n for the incomplete combustion of hydrocarbons:

CxHy + ((y+2x)/4)O2 → xCO + (y/2)H2O, where 'x' and 'y' are the number of moles of carbon atoms and hydrogen atoms respectively

General Eq^n for the complete combustion of hydrocarbons:

CxHy + ((y+4x)/4)O2 → xCO2 + (y/2)H2O, where 'x' and 'y' are the number of moles of carbon atoms and hydrogen atoms respectively

How do you draw a benzene ring?

Draw a hexagon and every second line draw another line inside the hexagon.

How is a benzene ring formed?

Each carbon is bonded to two other carbons and one hydrogen, leaving one delocalised electron in a p orbital. The orbitals overlap creating delocalised electrons in a ring. This causes the benzene ring to be very stable.

Isomers

Each of two or more compounds with the same formula but a different arrangement of atoms in the molecule and different properties.

An electron-deficient species which is therefore attracted to parts of a molecule that is electron-rich is called ____________________

Electrophile

How are esters formed?

Esters are formed when carboxylic acids react with alcohols in the presence of concentrated sulfuric acid as a catalyst and applied heat

Naming esters

First, with the alkanol, take away the anol and replace with yl. Second, with the carboxylic acid, replace to ate with ic.eg. Methanol Propanoic acid → Methyl Propanoate

pentan-2-ol and but-2-ene

Give the IUPAC name for the compounds below.

Reactivity

H-I>H-Br>H-Cl Increasing reactivity due to the decreasing stregth of the hydrogen halide bond down Group 17.

Ester in real life

Have a sweet, fruity smell and are used in the natural and synthetic flavors and smells in ice-creams, lilies, flowers, and fruits. Controversial use: as plasticizers

Step 1 for naming compounds

Identify the longest continuous chain of carbon atoms in the compound.

(R-Kesang's Table) Step 4 for naming compounds

If the compound has more than one functional group, the group nearest to the top of the list is the PRINCIPAL group in the compound and is named using the SUFFIX form.

Equation to find IHD

In a molecule with the formula CcHhNnOoXx, where X is a halogen atom, the IHD is given by: IHD=1 2×[2c+2−h−x+n]

Process of initiation.

In the presence of UV-light sufficient energy is available to break the Cl-Cl bond to produce two chlorine radicals. eg. Cl₂→(Uv-light)→2Cl∙

Infrared spectroscopy (IR)

Infrared (IR) spectroscopy is a technique that identifies compounds and determines structure.

____________ _________________can be used to determine the type of bonds in a compound based on their % absorption of infrared rays

Infrared spectroscopy

Summary of free-radical substitution

Initiation: increase in the number of free radicals. • Propagation: no change in the number of free radicals. • Termination: decrease in the number of free radical

Primary alcohol

It has one carbon atom attached to the C with the -OH group

Naming ketones

Ketones require at least three carbons. The functional group will NOT be at the end of the chain. A number is required if there is more than one possibility (from pentane onwards). The ending is -one-

Alkanes have intermolecular __________

London dispersion forces of attraction

Markovnivov's rule

Markovnikov's rule helps to determine which atoms in an electrophile join to which of the two carbon atoms in a C=C -The hydrogen and bromine can be bonded to two different spots (as shown by major and minor) *In other words, the carbon with the more hydrogen will gain more hydrogen -Major is used to describe the more likely structure -Markovnikov's rule only applies to asymmetrical alkenes where two products are possible (does not apply to ethene)

_____ __________________ determines relative atomic and molecular masses

Mass spectrometry

___________________ __________________ is used to determine relative atomic and molecular masses.

Mass spectrometry

Mass Spectrometry

Mass spectrometry (MS) is a techniques that identify compounds and determine structure.

List first six alkanes

Methane, Ethane, Propane, Butane, Pentane, Hexane

The number of smaller peaks a peak is split into, is called _______________

Multiplicity

When reducing aldehydes or ketones to primary or secondary alcohols respectively, use relatively good reducing agent like ______

NaBH4

_________________are electron-rich species containing a lone pair that is donated to an electron-deficient carbon

Nucleophiles

Step 2 for naming compounds

Number the carbon atoms in the PARENT chain from one end to the other so that the FUNCTIONAL groups are attached to atoms with the lowest possible numbers.

Step 7 for naming compounds

Numbers show which carbon atoms in the PARENT chain the functional groups are attached to, with the suffix group having the lowest possible number.

The color change observed throughout an oxidation reaction of alcohols when using acidified K2Cr2O7 is from _______

Orange to green

What type of substitution reactions does Alkanes undergo?

Photochemical free-radical substitution reaction. Halogenation.

Physical and chemical evidence for the structure of benzene

Physical - 1.look at carbon-carbon bond lengths and enthalpies. Chemical - Thermochemical evidence Only likes to undergo substitute reactions. Does not like to undergo addition reactions. Further-Isomers from C4H4Cl2

H^1NMR

Proton Nuclear Magnetic Resonance Spectroscopy; 1H NMR is a technique that identifies compounds and determines structure

What is the functional group for aldehydes?

RCHO, where 'R' is a general group of atoms

General formula of amines

RNH₂ where 'R' is the alkyl group

What is the functional group for ethers?

ROR

Functional groups

Reactive parts of molecules.

what does the basic reaction: carboxylic acid ⎯⎯⎯⎯⎯⎯⎯→ primary alcohol with (i) LiAlH4 in ethoxyethane (ii) H+/H2O show?

Reduction of carboxylic acids.

A two step reaction that involves the formation of a carbocation intermediate

SN1: Nucleophilic unimolecular substitution reaction

Why is SN2 called bimolecular nucleophilic substitution.

SN2 is called bimolecular nucleophilic substitution as 2 molecules are involved in the key(rate-determining) step.

_________________is a one step reaction that involves the formation of an unstable transition state

SN2: Nucleophilic biomolecular substitution reaction

Addition reaction of alkenes with halogens(Halogenation)

Same mechanism as with water; Alkenes react with halogens to produce dihalogen compounds

______________ alcohol has two carbon atoms attached to the C with the -OH group

Secondary

Step 6 for naming compounds

Several groups of the same type are identified by "di, tri, etc". Placed in front of the "prefix" or "suffix"

Predominant mechanism for tertiary halogenoalkanes

Sn1

Predominant mechanism for secondary halogenoalkanes

Sn1 & Sn2

Predominant mechanism for primary halogenoalkanes

Sn2

How do primary alcohols undergo oxidation?

The alcohol is heated under reflux with an excess of the oxidizing (put heat under arrow in equation) and using K2Cr2O7.

Exam tip (Electrophilic substitution, second stage)

The curly arrow in the first step in Figure 10.76 must come from the delocalised ring; and the partial ring in the second step must extend over five carbon atoms.

Process of Termination

The process is terminated when two radicals react eg. Cl∙+Cl∙→(UV)→CL₂ or CH₃∙+CL∙→(UV)→CH₃Cl or CH₃∙+CH₃∙→(UV)→C₂H₆ or

Naming ether (P2)

The shortest chain (when cut by oxygen) is said first with the ending of th or t (pent or meth) or otherwise, then 'oxy', then the longest chain is written as an alkane

Why is SN1 more favourable for tertiary halogenoalkanes?

This is because of the stability of the intermediate carbocation. Methyl groups (and alkyl groups in general) have an electron-releasing effect (also called a positive inductive effect) so that they are able to stabilise a positively charged carbon atom to which they are bonded.

How do tertiary alcohols undergo oxidation?

Trick question! Tertiary alcohols can't be oxidized since the carbon atom that holds the alcohol group has zero hydrogens attached to it.

How does partial oxidation of a primary alcohol occur?

Use acidified potassium dichromate (VI) or acidified potassium manganate (VII), under distillation.

Matching wave numbers with bonds(IR spectroscopy)

Using section 26 of the data booklet, we can determine the type of bond by referring to the wavelengths/number of the troughs that are in the IR spectrum.

When do we use the distillation method? What happens?

We use this only if we want an aldehyde. As the aldehyde has a lower boiling point than the alcohol, it evaporates, hence they move through a liebig condenser at the adjacent side

Alcohol incomplete combustion reactions

With less oxygen, methanol will undergo incomplete combustion: methanol: CH3OH(l) + O2(g) CO(g) + 2 H2O(l)

___________ are produced when electrons make transitions between inner energy levels.

X-rays

Hydrogenation of alkenes is a type of ____________ reaction.

addition

Basic reaction of reduction of aldehydes

aldehyde ⎯⎯⎯ primary alcohol with NaBH4 as catalyst and methanol

If there is no color change with the bromine water test, it indicates that it is an ________

alkane

An NMR spectometer can also work out the area under each peak to produce _________________

an integration trace

Suffix in IUPAC name for nitrile

anenitrile

___________ solvents are those that are not able to form hydrogen bonds

aprotic

Suffix in IUPAC name for arene

benzene

A ___________ is a positive ion with the charge centered on a carbon atom.

carbocation

In places where the waves are in phase, with the peaks still aligned, the waves are said to be in _______________ interference.

constructive

_______________ interference occurs at places where the waves are out of phase by 180°.

destructive

When the reaction is complete, the carboxylic acid is __________off

distilled

____________ is an electron- deficient species that is attracted to regions of relatively high electron density and accepts a pair of electrons to form a covalent bond.

electrophile

The nitration of Benzene occurs via _________ ____________

electrophilic substitution.

list from the most to least vulnerable species to a nucleophilic attack. bromoalkane, chloroalkane, iodoalkane, fluoroalkane.

fluoroalkane>chloroalkane>bromoalkane>iodoalkane

What happens in the first stage of electrophilic susbstitution(nitration of Benzene)?

formation of the electrophile: this is the nitronium ion, NO2 +, which is formed when concentrated sulfuric acid reacts with concentrated nitric acid: HNO3+H2SO4 → NO2 + +H2O+HSO4 −

Esters have low melting and boiling points because there are no _____ _________ _________, hence cannot form H- bonds and are insoluble in protic solvents.

free hydroxyl groups

The breaking of a covalent bond with both of the bonded electrons going to one of the atoms, forming a cation and an anion is called _____________ fission

heterolytic

If seeking to produce carboxylic acids from (primary) alcohols, the oxidising agent needs to be added in _______

high amounts/excess

Show the free-radical substitution process between Ethane and Bromine

initiation:Br2 ⎯→ 2Br• propagation: C2H6+Br• → •CH2CH3+HBr propagation: •CH2CH3+Br2 → CH3CH2Br+Br• termination: Br•+Br• → Br2 termination: Br•+•CH2CH3 → CH3CH2Br termination:•CH2CH3+•CH2CH3 → CH3CH2CH2CH3

The relative rate of reaction(from highest to lowest) of the different halogens in halogenoalkanes effected by the strength of the carbon-halogen bond for these alkanes when other variables are constant bromoalkane,iodoalkane,fluoroalkane,chloroalkane is

iodoalkane>bromoalkanes>chloralkanes>fluroalkanes because; the ease of breaking the bonds are C-I>C-Br>C-Cl>C-F

Basic reaction of reduction of ketones.

ketone ⎯⎯⎯ secondary alcohol with NaBH4 as catalyst and methanol.

The number of hydrogen atoms on adjacent carbons=?

multiplicity-1

When benzene is heated with a mixture of concentrated nitric and sulfuric acids, _____________ is formed:

nitrobenzene

The condensation/esterification reaction is a type of ______________ substitution reaction.

nucleophilic

Peaks in an H^1NMR spectrum correspond the _________________ in different chemical environments.

number/groups of hydrogen atoms /groups of protons

When calculating IHD from a molecular formula: Ignore ____________in the formula.

oxygen; e.g. C6H12O2 -based on CNH2N+2: for 6 C-atoms, 2(6)+2 = 14 H-atoms - ignoring O-atoms, there are 12 H-atoms IHD = 1 (i.e. a deficiency of 2 H-atoms)

Nitrobenzene can be reduced to______________ (aniline) by heating with a reducing agent such as a mixture of tin and concentrated hydrochloric acid.

phenylamine

SN1 reactions are favoured by _______, polar solvents.

protic

___________ waves are used in NMR and can give information about the environment of certain atoms.

radiowaves

The peak in the spectrum at the highest mass (m/z value) corresponds to the molecular ion and indicates the _______________ _____________ _______of the molecule

relative molecular mass

Stereochemical structural formula

shows the 3-D arrangement of atoms.

The SN2 mechanism is described as ______________because the 3-D arrangements of the reactants determines the 3-D configuration of the products.

stereospecific

Why is SN2 more favourable for primary halogenoalkanes than for tertiary halogenoalkanes?

steric effects: The alkyl groups surrounding the central carbon in a tertiary halogenoalkane make it much more difficult for the nucleophile to get in to attack the central carbon atom.

Chemicals/compounds with the same formula but different arrangements of atoms are called __________________

structural isomers

In a _________________ reaction, the halogen atom is replaced by an -OH group to give an alcohol

substitution

_____________ halogenoalkanes undergo SN1 reactions

tertiary

After ketone is produced, why is no further oxidation possible?

the carbon atom of the ketone has no more hydrogen attached to it

Oxidation

the process or result of oxidizing or being oxidized.

What is the IHD for C5H8NOCl?

• The general formula 'CnH2n+2': 2(5)+2 = 12 • ignore O but add another H due to N, so molecule has 9 H-atoms • However, there is 1 Cl, so subtract 1 from 9 to get 8 "H-atoms" ∴ (12 - 8)/2 = 4/2 = 2 = IHD