Chem 2 test 1

What are the rules for naming alkenes?

1. replace -ane suffix with -ene 2.Make sure the parent chain contains the double bond 3.Number the carbon atoms in the parent chain -start with side nearest to the double bond 4.Give the position of the double bond as a number -use the lowest numbered carbon in the double bond -place the number directly before the parent name 5. Use the suffixes --diene (2 double bonds), --tiene (3 double bonds), and --tetrene (4 double bonds) when more than one bond is present

dec-

10 carbons

eth-

2 carbons

shows us how the atoms in a molecule are bonded

2-D representation

saturated hydrocarbons

alkanes

-acyclic unsaturated hydrocarbon that contains one or more carbon-carbon double bonds -C=C functional group -use the -ene suffix (signifies presence of double bond)

alkenes

carbon-carbon double bonds

alkenes

alcohols are classified by how many _____________ are directly bonded to the carbon containing the hydroxyl group -determines how alcohol will react

alkyl groups

specific type of substituent; group of atoms obtained by the removal of 1 hydrogen atom from methane

alkyl groups

substitution of an alkyl group for a hydrogen requires a catalyst

alkylation

Cis-trans isomerism is not possible in ____________.

alkynes

acyclic unsaturated hydrocarbon that contains one or more carbon-carbon triple bonds

alkynes

carbon-carbon triple bonds

alkynes

What is a dehydrogenation reaction?

an alkene synthesis

What are the IUPAC rules for naming alcohols with multiple hydroxyl groups?

1. Follow original IUPAC rules 2. For more than one hydroxyl group, use the greek prefixes with the suffix -ol -diol-> 2 hydroxyl groups -triol-> 3 hydroxyl groups 3. Do not drop the 'e' from the parent chain

Match the following structural formula with compound types in the response list: CH3-S-CH3 A. disulfide B. thioether C. diol D. thiol

B.

A general method for preparing alcohols is the A. combustion of ethers B. hydrogenation of alkenes C. hydration of alkenes D. combustion of alkanes

C

which of the following could not be the molecular formula for an alkane molecule? -C4H10 -C24H50 -CH4 -C5H14

C5H14

prop-

3 carbons

but-

4 carbons

pent-

5 carbons

hex-

6 carbons

hept-

7 carbons

oct-

8 carbons

non-

9 carbons

For the following pair of compounds, select a correct structural characterization from the response list: 1-butanol and 2-butanol A. are constitutional isomers B. have the same number of carbon atoms but a different number of oxygen atoms C. have the same number of carbon atoms and the same number of oxygen atoms but are not constitutional isomers D. have the same number of oxygen atoms but a different number of carbon atoms

A

In chemical reactivity, ethers resemble A. alkanes B. alkenes C. phenols D. alcohols

A

Alcohols have higher boiling points than alkanes of similar molecular mass because A. hydrogen bonding occurs between alcohol molecules but not between alkane molecules B. alcohols are acidic and alkanes are not C. alkane molecules are polar and alcohol molecules are not D. alcohols are ionic compounds and alkanes are covalent compounds

A.

The sulfhydryl functional group is found in A. Neither thiols nor disulfides B. thiols C. disulfides D. both thiols and disulfides

B

naturally occurring phenol protects other substances from being oxidized

antioxidants

naturally occurring phenol mouth wash and throat lozenges

antiseptics

Unsaturated cyclic hydrocarbons that do not readily undergo addition reactions. -bonding differs from alkenes and alkynes -experimentally proven that all carbons are identical -double bonds are free to move around the ring

aromatic hydrocarbons

highly unsaturated carbon ring that contains both localized and delocalized bonds

aromatic ring system

delocalized bonding of 6 membered carbon rings

aromatics

saturated hydrocarbons in which all carbons are connected in cyclic arrangement

cycloalkanes

cyclic unsaturated hydrocarbon that contains one or more carbon-carbon double bonds within the ring system -C=C functional group -ene suffix

cycloalkenes

What are the three ways to depict alkanes?

dash-wedge-line structure ball and stick model space filling model

chemical reaction where water is formed from the removal of H and OH from a single reactant

dehydration reaction

chemical reaction where a hydrogen atom is lost from each of the 2 adjacent carbons and are replaced with a double bond

dehydrogenation reaction

-covalent bond where electrons are shared between more than two atoms -circle represents this

delocalized bond

What is the boiling point of alkanes and cycloalkanes?

increases with increasing number of carbons in the chain decreases with branching

compounds that contain elements besides carbon and hydrogen

inorganic compounds

Are alkanes and cycloalkanes soluble or insoluble in water?

insoluble

what are physical properties of aromatic hydrocarbons?

insoluble in water density less than water mostly liquid at room temperature

does the following meet the bonding requirement for carbon atoms? -3 single bonds and one double bond -2 double bonds

no yes

Tertiary alcohol produces _____________.

no reaction

What is the solubility of alkanes?

nonpolar molecules insoluble in water

compounds that have the same molecular formula but different in the way atoms are arranged; different compounds with different properties

isomers when you change the way that atoms are bound to one another, you change the properties

rubbing alcohol, ingestion causes vomiting

isopropyl alcohol (2-propanol)

Oxidation of a secondary alcohol produces ______________.

ketone

means it is in the plane

line

lines represent carbon-carbon bonds point of every line represents a carbon atom end of every line represents a carbon atom

line angle structural formula

volatile---primary constituents of gasoline skin irritant---causes drying can cause lung tissue damage if swallowed 5 to 8 carbons

liquid

ingestion can cause blindness and acidosis

methanol

the study of hydrocarbons and their derivatives

organic chemsitry

increase in C-O bonds or decrease in C-H bonds

organic oxidation

decrease in C-O bonds or increase in C-H bonds

organic reduction

-OH group is attached to a carbon atom that is part of an aromatic ring system. -aryl group (Ar)-aromatic ring system -general formula Ar-OH

phenols

flammable (like alcohols) halogenation reactions similar to alcohols can be oxidized, but occurs differently than alcohols cannot be dehydrated (unlike alcohols) chemical properties of ________________?

phenols

slightly soluble in water low melting solids or oily liquids at room temperature antiseptic and disinfectant properties Physical properties of ___________?

phenols

secreted or excreted by insects, animals, and plants triggers response within the same species

pheromones

What is the density of alkanes and cycloalkanes?

range from 0.6-0.8 g/mL layers on top when mixed with water

gives you an idea of how far the orbitals extend

space filling models

isomers that have the same molecular and structural formula but have different orientations in space

stereoisomers

an atom or group of atoms that are attached to a carbon chain

substituent

Aromatic hydrocarbons undergo two types of ______________ reactions known as ________________ and __________________.

substitution halogenation alkylation

when a small molecule replaces an atom or groups of atoms on a hydrocarbon usually results in a mixture of products

substitution reaction

organic compound that contains two or more 5-carbon isoprene units

terpenes

What are naturally occurring alkenes?

terpenes and pheromones

organic compound that contains a sulfur atom attached to two. carbon atoms by single bonds sulfur analogs of ethers

thioethers

organic compound that contains a sulfhydryl group attached to a saturated carbon atom sulfhydryl functional group sulfur analogs of alcohols

thiols

True or False carbons in double bond must have different groups attached for cis trans isomerism to be possible

true

True or false: More isomers for alkenes than alkanes because of double bonds

true

true or false Alcohols have higher boiling points and increased solubility when compared to alkanes

true

hydrocarbon in which the carbon chain contains at least one carbon-carbon double bond or one carbon-carbon triple bond -physical properties similar to saturated hydrocarbons -chemically more reactive

unsaturated hydrocarbons

compound that contains carbon- carbon multiple bonds double or triple bonds

unsaturated hydrocarbons the more double/ triple bonds, the less hydrogen

addition of an unsymmetrical small molecule

unsymmetrical addition reaction

What is the boiling point of alkenes/ cycloalkenes?

usually lower than an alkane with the same number of carbons

means carbon is coming out of a plane towards you

wedge

constitutional isomers that possess the same carbon-atom arrangement and that have differing locations for functional groups present

positional isomers

compound that contains only carbon and hydrogen single bonds

saturated hydrocarbons

constitutional isomers that possess different carbon atom arrangements and that contain identical functional groups if functional groups are present

skeletal isomers

semi solid used as a skin skin protectant ex:vaseline 18 to 30 carbons

solid

addition of a symmetrical small molecule

symmetrical addition reaction

substituents are "across from" one another

trans

isomer that has the substituents "across from" one another

trans prefix

Secondary alcohol produces ___________.

ketone

Primary alcohol produces __________.

aldehyde

what is hydrogen bonding alcohols?

-alcohols are able to participate in hydrogen bonding -hydrogen that is attached to a an electronegative atom interacts with the lone pairs on an electronegative atom in a different molecule -needs extra energy to break the bond

What is the boiling point of alcohol?

-boiling point of alcohol in water increases with increasing number of carbons -additional hydroxyl group will increase the boiling point -caused by an increase in hydrogen bonding

What ways can carbon bond?

-four single bonds -two single bonds and one double bond -two double bonds -one triple bond and one single bond NEED TO ADD UP TO 4 BONDS

What are the physical properties of alkynes?

-insoluble in water -density less than water -boiling point increases with MW

What is the solubility of alcohol?

-solubility of alcohol in water decreases with an increasing number of carbons -alcohol molecules are both polar and non polar -additional hydroxyl groups will increase polarity and therefore solubility

What are the chemical properties of alkynes?

-undergoes combustion reactions -addition reactions similar to alkenes -alkenes form an alkane -alkynes form as alkene

What are the chemical properties of aromatic hydrocarbons?

-unresponsive to addition reactions because of delocalized bond -undergoes substitution reactions -similar alkanes -alkylation -halogenation

meth-

1 carbon

What are the rules for cycloalkenes?

1. For substituted cycloalkenes with one double bond: do not need to number the double bond when the compound contains just one double bond 2. For unsubstituted cycloalkenes with one double bond: the carbon atoms are numbered so that the substituent will have the lowest numbered carbon 3. For cycloalkenes with more than one double bond: assign one double bond the numbers 1 and 2 and then assign the other double bond the lowest numbers possible.

What are IUPAC rules for naming ethers?

1. For unsymmetrical ethers, name both alkyl groups -name in alphabetical order -add ether to end of name -separate all words with a space 2. For symmetrical ethers, name the alkyl group and use the prefix di- -add ether to end of name separate all words with a space

What are the IUPAc rules for naming alcohols?

1. Identify and name the longest parent chain with that has the hydroxyl group -drop the 'e' and add the -ol 2. Number the carbon atoms in the parent chain -start with the side nearest to the hydroxyl group -takes precedent over double/triple bonds 3. Locate and name any substituents 4. When the -OH group is attached to a carbon ring, start numbering at the hydroxyl group -count clockwise or counter clockwise to give any substituents the next lowest number

What are the rules for naming branch chain alkanes?

1. Identify the longest continuous chain and name it 2. Number the carbons in the parent chain 3. If only one alkyl group is present, locate and name it 4. If two or more of the same alkyl groups are present, use greek prefixes 5. If two or more different alkyl groups are present, identify their location and name -list the names of the alkyl groups in alphabetical order 6.Follow IUPAC punctuation

What are the cycloalkane rules when dealing with IUPAC?

1. If there is only one ring substituent, it does not need to be numbered 2. When 2 ring substituents are present, the carbons are numbered starting with the substituent that has the highest alphabetical priority 3. When 3 or more ring substituents are present, the ring is numbered so that the substituent numbers are the lowest

What are the rules for common naming systems of alcohols?

1. Name all the carbon atoms as a single group 2. Add the word alcohol, separated by space

What is the general molecular formula of an alkane?

CnH2n+2

Match the following structural formula with compound types in the response list: HO-CH2-CH2-OH A. thiol B. disulfide C. thioether D. diol

D

What are hydrocarbons?

Hydrocarbons are organic compounds

systematic naming of compounds necessary as the number known compounds increased

IUPAC nomenclature

What is the nomenclature of alkynes?

IUPAC rules stay the same as alkenes uses the -yne suffix

What is the nomenclature of phenols?

IUPAC rules the same as benzene parent name is phenol start counting at -OH group

What does IUPAC stand for?

International Union of Pure and Applied Chemistry

Why are there so many organic compounds?

One reason why so many organic compounds exist is because of the ability for isomers to form.

organic compound that contains an -OH group bound to a saturated carbon atom

alcohol

hydrocarbons can be ___________ or ______________

acyclic (linear) or cyclic

chemical reaction where atoms or groups of atoms are added to each carbon atom that is in a carbon-carbon double bond. unsymmetrical and symmetrical

additional reactions

each model is represented as a ball and the sticks represent the bonds to the other atoms

ball and stick models

what is the simplest aromatic hydrocarbon?

benzene

substituents are "on the same side" of the double bond.

cis

isomer that has the substituents "on the same side"

cis prefix

reaction between a substance and oxygen that produces heat and light products are carbon dioxide and water

combustion reaction

reaction between a substance and oxygen that produces heat and light products are carbon dioxide and water exothermic

combustion reaction

reaction between a substance and oxygen that produces heat and light. Products are carbon dioxide and water

combustion reaction

When naming branch chain alkanes....

comma between the numbers hyphen between number and alkyl group no space between alkyl group name and parent chain

reaction where two molecules combine to form a larger one and water is formed. Mostly primary alcohols (secondary and tertiary alcohols most often dehydrated)

condensation

uses groupings of atoms and only shows the bonds on the central atoms

condensed structural formula

specific 3-D arrangement of atoms in a molecule -result from being able to rotate the carbon-carbon bond -carbon carbon triple bonds cannot be rotated

conformation

isomers that differ in the order in which the atoms are attached to eachother

constitutional isomers

Which of the following is true concerning organic compounds is correct? a. organic compounds are always soluble in water b. organic compounds are only found in nonliving systems c. organic compounds cannot be found in nature; they must be synthesized in a laboratory d. organic compounds always contain the element carbon

d.

means that an atom is coming behind the plane away from you

dash

What are three dimensional structural representations?

dash wedge line structure ball and stick model space filling model

naturally occurring phenol lysol sprays and wipes

disinfectants

How many carbons are present in the alkane whose IUPAC name is 2,2,4-trimethylpentane?

eight

alcoholic beverages, gas acetaldehyde responsible for hangover symptoms

ethanol

flammable (like alcohols) react slowly with oxygen in the air to form unstable hydroperoxides and peroxides unreactive to acids, bases, and oxidizing agents (like alkanes) combustion and halogenation reactions possible

ether chemical properties

boiling point similar to alkanes (much lower than alcohols) more soluble in water than alkanes (similar solubility to alcohols) antiseptic and disinfectant properties

ether physical properties

organic compound where an oxygen is bound to two carbon atoms by single bonds

ethers

major ingredient in antifreeze and deicer products; extremely toxic oxalic acid can crystallize in kidneys

ethylene glycol (1,2-ethanediol)

shows all atoms and bonds

expanded structural formula

What are two dimensional structural representations?

expanded structural formula condensed structural formula skeletal structural formula line angle structural formula

True or false primary, secondary, and tertiary will not tell us how alcohol will react

false

naturally occurring phenol found in plants

flavoring/ antibacterial agents

constitutional isomerism is possible in alkanes only if the number of carbon atoms present is ______________.

four or more

structural feature that is directly involved in most chemical reactions the molecules participate in (reactive part of molecule)

functional group

constitutional isomers that contain different functional groups

functional group isomers

structural feature that is directly involved in most chemical reactions the molecule participates in -consists of the carbon-carbon double and/or triple bonds within unsaturated hydrocarbons

functional groups

odorless, colorless, and nontoxic can cause suffocation due to lack of oxygen 1-4 carbons

gas

What are the physical states of alkenes/cycloalkenes? Carbons?

gas-> 2-4 carbons liquid-> 5-17 carbons solid-> 18 or carbons

lotion, soap, shaving cream, candy, and icing. naturally occurring in body --product of fat metabolism

glycerol (1,2,3-propanetriol)

substitution of a halogen atom for a hydrogen requires a catalyst

halogenation

substitution where the hydroxyl group was located. No catalyst needed, but heat is required. Forms an alkyl halide

halogenation

addition of two halogen atoms, added at the double bond, no catalyst needed

halogenation reaction

reaction between a substance and a halogen where 1 or more halogen atoms are added

halogenation reaction

addition of water molecule across the double bond catalyst required

hydration of alkenes

addition of a water molecule, added at the double bond, catalyst required

hydration reaction

compound that contains carbon and hydrogen atoms plus as additional atom *always organic

hydrocarbon derivatives

compounds that contain only hydrogen and carbon atoms

hydrocarbons

What are 2 symmetrical addition reactions?

hydrogenation and halogenation

addition of an H2 molecule, added at a double bond, catalyst required.

hydrogenation reaction

what are 2 unsymmetrical addition reactions?

hydrohalogenation and hydration reactions

addition of a hydrogen halide molecule, added at a double bond, no catalyst needed.

hydrohalogenation reaction

specific name for the OH functional group

hydroxyl group

the study of all other compounds

inorganic chemistry

What is the solubility of alkenes and cycloalkenes?

insoluble in water

Why is it important to know the physical properties of alkanes and cycloalkanes?

is it important to know the physical properties of alkanes and cycloalkanes because the effects of alkanes on the human body depend on the physical state of the alkane

compounds that have the same molecular formula but different in the way the atoms are arranged

isomers