EFN214G Lífræn efnafræði
Benzophenone
A ketone with benzene rings on both sides. (meso)
Polymer
A long molecule consisting of many similar or identical monomers linked together.
Newman projection
A method of visualizing a compound in which the line of sight is down a carbon-carbon bond axis.
optical activity
rotation of the plane of polarized light
chiral molecule
A molecule having at least one pair of enantiomers.
cyclohexanol
same as hydroxycyclohexane.
benzyl
CH2 + benzene ring. When it is considered as a substituent.
Ethyl
CH2CH3
Methyl
CH3
Butyric acid
CH3CH2CH2COOH
Propionic acid
CH3CH2COOH
isoprophyl
CH3CHCH3. A three carbon alkyl group
Acetic acid
CH3COOH.
Lindlar's catalyst
specially prepared form of palladium metal.
Ethylene
systematic name: Ethene. H2C=CH2
Benzyl alcohol
systematic name: phenylmethanol.
Allyl alcohol
systematic name: prop-2-en-1-ol.
Hydrogenation
The process of converting unsaturated fats to saturated fats by adding hydrogen.
Acyl group
When our -COR group is a substituent.
homolytic cleavage
When the bond breaks and each atom gets one electron.
heterolytic cleavage
When the bond breaks, the most electronegative atom gets both electrons.
Reactions of alcohols
dehydration and oxidation
Ortho
prefix for when benzene has two substituents in a 1,2 position.
Meta
prefix for when benzene has two substituents in a 1,3 position.
polar reactions
processes that involve unsymmetrical bond-breaking and bond-making.
Carboxylic acid chloride
Contains an O=C-Cl group attached at the C. -Ethanoyl chloride.
aldol
Contains both aldehyde and alcohol functional groups.
Acrylic acid
H2C=CH-COOH
formic acid
HCOOH.
Succinic acid
HO2CCH2CH2CO2H
Malonic acid
HO2CCH2CO2H
Oxalic acid
HO2CCO2H
Glutaric acid
HOOC-(CH2)3-COOH
Adipic acid
HOOC-(CH2)4-COOH
phenoxide ion
(ArO-) formed when phenols dissociate to a slight extent in dilute aqueous solution by donating a proton to water, generating H3O+.
constitutional isomers
(Byggingarhverfur) differ in the order of attachment of atoms
Conjugate (1,4) nucleophilic addition reaction
(Nucleophilic addition reaction of aldehydes and ketones.)
Reaction with Grignard reagents to yield alcohols
(Nucleophilic addition reaction of aldehydes and ketones.)
Reaction with alcohols to yield acetals
(Nucleophilic addition reaction of aldehydes and ketones.)
Reaction with amines to yield imines
(Nucleophilic addition reaction of aldehydes and ketones.)
Reaction with hydride reagents to yield alcohols
(Nucleophilic addition reaction of aldehydes and ketones.)
Secondary alkyl halide
(R2CHX) SN2 substitution predominates if a weakly basic nucleophile is used; E2 elimination predominates if a strong base is used; and E1cB elimination takes place if the leaving group is two carbons away from a carbonyl group (HO-C-CH-C=O)
Tertiary alkyl halide
(R3CX) E2 elimination occurs when a base is used, but SN1 substitution and E1 elimination occur together under neutral or acidic conditions. E1cB elimination takes place if the leaving group is two carbons away from a carbonyl group (HO-C-CH-C=O)
Primary alkyl halide
(RCH2X) SN2 substitution occurs if a nucleophile such as I-, Br-, RS-, NH3, or CN-, is used; E2 elimination occurs if a strong base such as OH- or an alkoxide ion (RO-) is used; and E1cB elimination occurs if the leaving group is two carbons away from a carbonyl group (HO-C-CH-C=O).
alkoxide ion
(RO-) formed when alcohols dissociate to a slight extent in dilute aqueous solution by donating a proton to water, generating H3O+.
Grignard reaction with carbonyl compounds
(Synthesis of alcohols)
diastereomers
(Víxlhverfur/fjölhverfur) stereoisomers that are not mirror images
Friedel-Crafts Alkylation
(of benzene) A reaction that is carried out by treating the aromatic compound with an alkyl chloride, RCl, in the presence of AlCl3 to generate a carbocation electrophile R+. Aluminum chloride catalyzes the reaction by helping the alkyl halide to dissociate in much the same way that FeBr3 catalyzes aromatic brominations by helping Br2 dissociate. Loss of H+ then completes the reaction.
configuration
(of chiral molecules) The four atoms attached to the central carbon must be ranked according to atomic number (E, Z rules). If the ranking of highest to lowest can be counted in a right turn (réttsælis) then we have a R ________, but if it goes to the left (rangsælis) we have an S ________. The number of possible stereoisomers is 2^n where n is the number of stereocenters (chirality centers), minus any meso stereoisomer.
stereocenter
(or chirality center) A carbon atom bonded to four different groups, can be more than one in a single molecule. If n is the number of chirality centers, then the number of stereoisomers is 2^n
Stereoisomers
(rúmhverfur) Compounds with the same structural formula but with a different arrangement of the atoms in space.
Synthesis of sulfides
(sjá mynd)
Synthesis of thiols
(sjá mynd)
Reactions of phenols
(sjá mynd) Quinones Hydroxyquinones Ubiquinone
Reduction of carbonyl compounds
(synthesis of alcohols)
conformation
- Different arrangements of atoms resulting from rotation about a single bond
Claisen Condensation Reaction
- the aldol reaction with an ester. - deprotonation of the α-C of an ester and the addition of the anion to the carbonyl carbon of a second ester. - forms a β-ketoester - has a biological application in fatty acid synthesis
Nucleophilic substitution reaction
-SN1 and SN2 -nucleophile forms a bond with a carbon and a leaving group leaves.
Meso compounds
-have chiral centers -overall molecule is achiral -have internal plane of symmetry -not optically active --> don't rotate plane polarized light -each chiral center rotates light in opposite directions so overall the rotations cancel out
Williamson Ether Synthesis
1. Multiple Possible Reactants 2. SN2; therefore, least substituted alkylhalide is the best. Produces ethers from the reaction of metal alkaloids with primary alkyl halides.
Enolate ion
A carbanion adjacent to a carbonyl group. Typically undergoes protonation on the alpha carbon to give a saturated aldehyde or ketone product.
Allylic carbocation
A carbocation in which the positive charge is adjacent to a carbon-carbon double bond.
acetylide anion
A carbon nucleophile generated by treating 1-alkynes with a very strong base, such as sodium amide.
Aldehyde
A compound containing a -CHO group. Gets the ending -al.
Halide
A compound formed with a halogen. -Chloromethane
Monophosphate
A compound that contains one phosphate and four oxygen atoms. - Methyl phosphate
Amide
A compound that has a carbonyl group (C=O) bonded to nitrogen. They are named by dropping the -oic in the corresponding acid and adding -amide. Substituents attached to the nitrogen are listed following N-. Ethanamide
Ether
A compound that has an oxygen attached to two alkyl groups. -Dimethyl ether. (R-O-R')
Pyridine
A nitrogen containing heterocyclic analog of benzene. Like benzene, it is a flat, aromatic molecule with bond angles approximately 120°. Six pi electrons in a cyclic conjugated pi orbital system. The lone pair electrons are not part of the pi orbital system but instead occupy an sp2 orbital in the plane of the ring and are available for donation to an acid -> Basic compound.
electrophilic aromatic substitution
A reaction in which an electrophile is substituted for a hydrogen on an aromatic ring. Halogenation, Nitration, Sulfonation, Alkylation, Acylation.
radical reaction
A reaction in which bonds are made by donation of one electron from each of two reactants and in which bonds are broken when each fragment leaves with one electron
E,Z system
A system used to specify the configuration of groups about a carbon-carbon double bond. If the higher-ranked groups on each carbon are on opposite sides of the double bond, the alkene is said to have E stereochemistry. If the higher-ranked groups are on the same side, the alkene has Z stereochemistry. 1. Sætistala 2. Samskonar atóm -> næsta atóm. 3. Fjöltengi.
Cyclohexanecarbaldehyde
Aldehyde.
Crotonaldehyde
Aldehyde. Systematic name: But-2-enal. Structure: CH3CH=CHCHO
Acetaldehyde
Aldehyde. Systematic name: Ethanal. Structure: CH3CHO
Formaldehyde
Aldehyde. Systematic name: Methanal. Structure: HCHO
Acrolein
Aldehyde. Systematic name: Propenal. Structure: H2C=CHCHO
Alkylamines
Alkyl-substituted amines
nucleophile
An atom (or group of atoms) that is attracted to an electron- deficient (positive) centre or atom, where it donates a pair of electrons to form a new covalent bond.
electrophile
An atom (or group of atoms) that is attracted to an electron-rich (negative) centre or atom, where it accepts a pair of electrons to form a new covalent bond.
organohalide
An organic compound containing at least one halogen.
Ketone
An organic compound containing the -CO- group where the C is connected to other molecules. -Propanone. Gets the ending -one.
E2 reaction
C-H and C-X bonds break simultaneously, giving the alkene in a single step without intermediates. The reaction takes place when an alkyl halide is treated with a strong base, such as hydroxide ion or alkoxide ion.
E1 reaction
C-X bond breaks first to give a carbocation intermediate, followed by base removal of a proton to yield the alkene. Neutral or acidic conditions.
prophane
C3H8
butane
C4H10
phenyl
C6H5 group. When the benzene ring is considered as a substituent.
benzene
C6H6
Carbonyl compounds
Compounds that contain the functional group C=O where the C is connected to two other atoms. Two categories: -Aldehydes and ketones -Carboxylic acids and their derivatives.
primary alcohol
Eingreint alkóhól. Ef við oxum það einusinni fáum við aldehyde og ef við oxum það svo fáum við carboxylic acid.
Bromination
Electrophilic aromatic substitution, + Br2 and FeBr3.
Chlorination
Electrophilic aromatic substitution. Cl2, FeCl3
unsaturated
Fat with less than the maximum number of hydrogens in one or more of its fatty acid chains. When carbon chains contain double or triple bonds.
saturated
Fats with the maximum number of hydrogens.
Hydrogenation of aromatic rings
H2 og PtO2 catalyst
Alkenes
Hydrocarbons with one or more carbon-carbon double bonds.
Markovnikov's Rule
In the addition of HX to an alkene, the H attaches to the carbon with fewer alkyl substituents and the X attaches to the carbon with more alkyl substituents.
Zaitsev's Rule
In the elimination of HX from an alkyl halide, the more highly substituted alkene product predominates.
tautomers
Isomers that can interconvert by exchanging the location of a proton.
Oxidation of aromatic side chains
KMnO4 og H2O
Acetone
Ketone. Structure: CH3COCH3
Reactivity of carboxyl acid derivatives
More reactive carboxylic acids can be converted into less reactive ones, but not the other way around.
Alpha substitution reaction
Occurs at the position next to the carbonyl group - the alpha position - and results in the substitution of an alpha hydrogen atom by an electrophile (E) through either an enol or enolate ion intermediate.
Friedel-Crafts Acylation
Occurs when an aromatic compound is treated with a carboxylic acid chloride (RCOCl) in the presence of AlCl3, an acyl group (R-C=O) is introduced onto the ring. For example, reaction of benzene with acetyl chloride yields the ketone acetophenone.
Amides
RCONH2. Those with an unsubstituted -NH2 group are named by replacing the -oic acid or -ic acid ending with -amide, or by replacing the -carboxylic acid ending with -carboxamide. If the nitrogen atom is substituted, it is named by first identifying the substituent groups and then the parent chain. The substituents are preceded by the letter N to identify them as being directly attached to nitrogen.
Thioester
RCOSR'.
pent-
Prefix - 5 carbons.
hex-
Prefix - 6 carbons.
hept-
Prefix - 7 carbons.
Para
Prefix for when benzene has two substituents in a 1,4 position.
Nitriles
R-C triple bond N. Simple ones are named by adding -nitrile as a suffix to the alkane name, with the nitrile carbon numbered C1. More complex ones are named as derivatives of carboxylic acids by replacing the -ic acid or -oic acid ending with -onitrile, or by replacing the -carboxylic acid ending with -carbonitrile. In this system, the nitrile carbon atom is attached to C1 but is not itself numbered.
carboxylic acid
R-COOH. Simple open chained ones are named by replacing the terminal -e of the corresponding alkane name with -oic acid. The -COOH carbon is numbered C1. If referred to as a group it gets the ending -yl, t.d. formic acid becomes a formyl group.
imines
R2C=NR'. Are formed when ammonia and primary amines (R'NH2) add to aldehydes and ketones. The reaction occurs by nucleophilic addition of the amine to the carbonyl group, followed by loss of water from the amino alcohol addition product.
Acid anhydrides
RCO2COR'. Symmetrical ones from simple carboxylic acids and cyclic ones from dicarboxylic acids are named by replacing the word acid with anhydride. Unsymmetrical ones (prepared from two different carboxylic acids) are named by citing the two acids alphabetically and then adding anhydride.
Acyl phosphate
RCO2PO3(2-) or RCO2PO3R'(-). A carboxylic acid derivative with a phosphate leaving group.
Acid halides
RCOX. Named by identifying first the acyl group and then the halide. Those carboxylic acids that take a -carboxylic acid ending use -carbonyl for the name ending of the corresponding acyl group.
Grignard reagent
RMgX, compounds that are examples of organometallic compounds because they contain a carbon-metal bond. X: Cl, Br, I. R: 1°alkyl, 2°alkyl, 3°alkyl, alkenyl, aryl. Mjög skautuð sameind, getum hugsað hana sem tvær skautaðar sameindir, -CH3 og +MgI. Hvörf: -við formaldehyde --> 1° alcohol -við aldehyde --> 2°alcohol -við ketone --> 3° alcohol -við ester --> 4° alcohol (tveir af nýju hópunum koma frá Grignard efninu.
Sulfonation
Replacement of a hydrogen atom by a sulfonic acid group (-SO3H) on a benzene ring. Catalyst: H2SO4
Cycloalkanes
Saturated hydrocarbons with carbon atoms joined in a ring.
Isoprene
Systematic name: 2-Methylbuta-1,3-diene. H2C=C2H3-CH=CH2
Isobutylene
Systematic name: 2-Methylpropene. C3H6=CH2
tert-Butyl alcohol
Systematic name: 2-methylpropan-2-ol.
Propylene
Systematic name: Propene. CH3CH=CH2
Ethylene glycol
Systematic name: ethane-1,2-diol.
Glycerol
Systematic name: propane-1,2,3-triol
Carbonyl condensation reactions
Take place between two carbonyl partners and involve a combination of alpha substitution and nucleophilic addition steps. One partner is converted into its enolate ion and undergoes an alpha-substitution reaction when it carries out a nucleophilic addition to the second partner. The product is a beta-hydroxy carbonyl compound.
SN2
Takes place in a single step without intermediates when the entering nucleophile approaches the surface from a direction 180° away from the leaving group. Bimolecular: the rate of the reaction depends on the concentrations of *two* substances, alkyl halide and nucleophile. Reactivity decreases with more substitution groups.
SN1
Takes place only on tertiary substrates and only under neutral or acidic conditions in a hydroxylic solvent such as water or alcohol. Occurs by spontaneous loss of the leaving group before the incoming nucleophile approaches. Forms a carbocation intermediate, reactivity is higher for a more stable carbocation. Unimolecular because the rate of the reaction depends on the concentration of only *one* substance
E1cB reaction
Takes place through a carbanion intermediate. Base induced abstraction of a proton gives an anion, which immediately expels a leaving group on the adjacent carbon. This reaction is particularly common in substrates that have a poor leaving group, such as -OH, two carbons away from a carbonyl group, HO-C-CH-C=O.
Hydroxylation
The addition of hydroxyl groups to each of the two double bond carbons.
Leaving groups
The best ones are those that give the most stable anions.
chiral environment
The chiral surroundings or conditions in which a molecule resides.
Termination of polymerization
The end of the process, a reaction that consumes the radical. Combination of two growing chains is one possible chain-terminating reaction.
syn stereochemistry
The opposite of anti. A syn addition reaction is one in which the two ends of the double bond react from the same side. A syn elimination is one in which the two groups leave from the same side of the molecule.
anti stereochemistry
The opposite of syn. An anti addition reaction is one in which the two ends of the double bond are attacked from different sides. An anti elimination reaction is one in which the two groups leave from opposite sides of the molecule.
Secondary alcohol
Tvígreint alkóhól. Aðeins hægt að oxa það einusinni og fá ketón. Verður til við hvarf aldehydes og Grignard efnis.
Isomers
Two molecules that have the same chemical formula but different structures.
resonance structure
Two or more equally valid electron dot structures. Leads to stability, more structures, more stable substance. Structures differ only in the placement of the pi bond and nonbonding electrons.
Initiation of polymerization
When a few radicals are generated on heating a small amount of benzoyl peroxide catalyst to break the weak O-O bond. The benzoyloxy radical then adds to the C=C bond of ethylene to generate a carbon radical. One electron from the C=C bond pairs up with the odd electron on the benzoyloxy radical to form a C-O bond, and the other electron remains on the carbon.
Elimination reaction
When a single organic reactant splits into two products.
aldol reaction
When an aldehyde and ketone with an alpha hydrogen atom undergo a base-catalyzed carbonyl condensation reaction.
Propagation of polymerization
When the carbon radical formed in the initiation step adds to another ethylene molecule to yield another radical. Repetition of the process lengthens the chain.
Acetal
a carbon atom bonded to two -OR groups, one alkyl group and one hydrogen. Can serve as protecting groups for aldehydes and ketones.
Addition reaction
a chemical reaction in which two or more substances combine to form a new compound with no atoms "left over".
Disulfide
a compound containing an -S-S- group. -Dimethyl disulfide.
Carboxylic acid
a compound containing the -COOH functional group. -Ethanoic acid Derivatives of this compound can be: Acid halide, Ester, Thioester, Amide, Acid anhydride and Acyl phosphate.
Amine
a compound derived from ammonia by replacing hydrogen atoms by univalent hydrocarbon radicals. -Methylamine. They can be primary, secondary, tertiary (and quaternary) and it depends on the degree of substitution on the nitrogen atom. Basicity: Ammonia > Primary alkylamine > secondary alkylamine > tertiary alkylamine > Arylamine (aniline) > Heterocyclic amine (pyridine)
Alcohol
a compound formed with OH. -Methanol. Hydroxyl group bonded to a saturated sp3-hybridized carbon atom. (R-OH). Have unusually high boiling points due to hydrogen bonds.
Nitro
a compound that contains NO2. -Nitromethane
Thiol
a compound that contains an -SH group, R-SH. -Methenethiol
Sulfide
a compound that contains one sulfur atom. -Dimethyl sulfide.
aromatic compound
a compound that contains the ring structure of benzene.
Ester
a compound with the general formula RCOOR' (where R is a hydrocarbon group or a hydrogen and R' is a hydrocarbon group). It is formed from an alcohol and organic (or carboxylic) acid by removal of water (dehydration). -Methyl ethanoate. Named by first giving the name of the alkyl group attracted to oxygen and then identifying the carboxylic acid, with -ic acid replaced by -ate.
ring flip
a conformational change in which one chair conformation is converted into the other
Pyrrole
a five atom ring with one nitrogen atom and two double bonds. Aromatic. Has six pi electrons that are shared in the aromatic ring and therefore not available for donation to an acid -> Nonbasic.
uropygial gland
a gland near the upper base of the tail that secretes oils that a bird distributes across its feathers via preening
Alkanes
a hydrocarbon containing only single covalent bonds. - Ethene.
Malonic Ester Synthesis
a method for preparing a carboxylic acid from an alkyl halide while lengthening the carbon chain by two atoms
racemate
a mixture containing equal amounts of two enantiomers
rearrangement reaction
a molecule undergoes bond reorganization to yield an isomer.
achiral molecule
a molecule whose mirror images are superimposable, usually have a plane of symmetry through them.
skeletal structure
a representation of organic compounds that shows only the bonding of the carbon framework.
oxidation
addition of oxygen
mercapto group
an SH group
Hydration reaction
an addition reaction in which a hydrogen atom and a hydroxyl group from a water molecule add to a double or triple bond
Epoxide
an ether in which the oxygen is incorporated into a three-membered ring
benzylic position
any carbon atom attached directly to a benzene ring.
Arene
aromatic ring. -Benzene
arylamines
aryl-substituted amines
Phenol
benzene ring bonded to OH. Have unusually high boiling points because of hydrogen bonds.
Xylene
benzene with 2 methyl groups
Toluene
benzene with CH3
Aniline
benzene with NH2
Benzaldehyde
benzene with aldehyde. Systematic name: Benzenecarbaldehyde. Structure: C6H5CHO.
Benzoic acid
benzene with carboxylic acid
Styrene
benzene with ethene
Acetophenone
benzene with ketone.
Nitrile
carbon triple bonded to nitrogen. -Ethanenitrile.
ketones
carbonyl group is within a carbon skeleton.
Maleic acid
cis-HO2CH=CHCO2H
Imine
compound w/ a N atom double-bonded to a carbon atom. -Acetone imine
conjugated compounds
compounds that have alternating single and double bonds. Have distinctive characteristics.
alkyl halide
compounds with a halogen atom bonded to a saturated, sp3-hybridized carbon atom
enynes
compounds with both double and triple bonds. Named by giving the first multiple bond the lowest number, if possible, give the double bond a lower number than the triple bond. Give cis alkenes when reduced.
polycyclic aromatic compounds
contain two or more fused benzene rings and are often known to be carcinogenic.
-ane
ending for alkines, for a ring of atoms we add the prefix Cyclo-. The middle part of the name depends on how many carbon atoms are in the molecule.
preening
feather maintenance behaviour in which a bird tends to its feathers with its bill.
functional group
group of atoms within a molecule that interacts in predictable ways with other molecules.
cis-trans isomers
have the same covalent bonds but differ in spatial arrangements
enantiomers
isomers that are mirror images of each other (handhverfur) occurs whenever a tetrahedral carbon is bonded to four different substituents
levorotatory
refers to a substance that rotates the plane of polarized light to the left
dextrorotatory
refers to a substance that rotates the plane of polarized light to the right.
angle strain
results when bond angles deviate from their ideal values by being stretched or compressed
Heterocycles
ring structures that contain at least two different elements in the ring.
meta-Chloroperoxybenzoic acid
mCPBA
alkaloids
naturally occurring amines derived from plant sources, were once known as "vegetable alkali" because their aqueous solutions are slightly basic.
Alkyne
one or more triple bonds. -Ethyne
ectoparasites
parasites such as lice, ticks, flies and mites that inhabit the exterior of their host's body.
Cellulose
polysaccharide consisting of glucose monomers that reinforces plant-cell walls
pro-
prefix for 3 carbons
but-
prefix for 4 carbons
Fischer esterification
the formation of an ester from a carboxylic acid and an alcohol in acidic conditions
Iodination
the incorporation or addition of iodine in a compound by oxidation with H2O2.
Nitration
the substitution of a nitro group (-NO2) for a hydrogen on an aromatic ring. Catalyst: H2SO4
Fumaric acid
trans-HO2CH=CHCO2H
sawhorse representation
views the carbon-carbon bond from an oblique angle and indicates spatial orientation by showing all C-H bonds
substitution reaction
when two reactants exchange parts to give two new products.
oxidative cleavage
Þegar tvítengi er rofið og súrefni kemur í staðin á báðum "brotnu" endunum, ef tvítengdu kolefnin eru tengd við vetni þá fer súrefni inná milli og býr til OH hóp þar sem H var fyrir.
Tertiary alcohol
Þrígreint alkóhól. Ekki hægt að oxa það. Ef allir hóparnir eru mismunandi hefur það verið búið til úr ketóni og Grignard efni. Ef tveir af hópunum eru eins hefur það verið búið til úr ketóni eða ester, og Grignard efni.