Kaplan Organic Chem: Chapter 1

Question 1

carbonyl group

Answer 1

carbon double bonded to an oxygen

Question 2

aldehyde structure

Answer 2

carbonyl, R group, and H

Question 3

ketone structure

Answer 3

carbonyl group and 2 R groups

Question 4

alkanes

Answer 4

C_nH_2n+2

hydrocarbons that lack pi bonds

usually end with “ane”

methane, propane, butane

Question 5

steps to nomenclature

Answer 5

1. select parent chain –> longest chain
   
   • for chains with equal lengths, choose the one with more substituents
2. number the parent chain
   
   • give first substituent the lower possible number
   • if tie, choose chain where 2nd sub has the lower number
3. name the subsituents based on where and how many
4. arrange the subs alphabetically
   
   • place the locants in front of each substituent

Question 6

primary carbon

1°

Answer 6

depends on number of carbons directly attached

Question 7

secondary carbon

2°

Answer 7

Question 8

tertiary carbon

3°

Answer 8

Question 9

quarternary carbon

4°

Answer 9

depends on number of carbons directly attached

Question 10

Assessing Stability

Answer 10

1. correct electronegativity
2. size: bigger = more stable
3. more resonance = more stable –> pi bond being spread
4. induction: pull away from neg charged region more acidic –> sigma bonds
5. orbitals: triple bond more acidic
   
   1. lone pair - 25% sp3 less stable

Question 11

nomenclature

n-

Answer 11

“normal”

n-propyl –> straight chain alkane

Question 12

nomenclature

multiple substituents of the same type

Answer 12

di-, tri-, tetra- etc

Question 13

highlight the parent chain

Answer 13

longest chain must include hydroxyl group

Question 14

highlight the parent chain

Answer 14

Question 15

name substituents then name molecule

Answer 15

4-ethyl-2,3-dimethylheptane

Question 16

hydrocarbons

Answer 16

compounds that only contain carbon and hydrogen atoms

Question 17

alcohols

Answer 17

contain at least one OH group

Question 18

alkyl halides

Answer 18

alkanes with halogen subsituents

fluoro-, chloro-, bromo-, iodo-

Question 19

alkene

Answer 19

alkanes with double bonds

Question 20

alkyne

Answer 20

alkanes with triple bonds

Question 21

alkane name

1 carbon

Answer 21

methane

Question 22

alkane name

2 carbons

Answer 22

ethane

Question 23

alkane name

3 carbons

Answer 23

propane

Question 24

alkane name

4 carbons

Answer 24

butane

Question 25

alkane name 5 carbons

Answer 25

pentane

Question 26

alkane name 6 carbons

Answer 26

hexane

Question 27

alkane name 7 carbons

Answer 27

heptane

Question 28

alkane name 8 carbons

Answer 28

octane

Question 29

alchol nomenclature

Answer 29

-ol chain is numbered so C attached to OH gets lowest possible number (even when multiple bonds present) if alc is not highest priority function group --\> hydroxy-

Question 30

common name of ethanol

Answer 30

ethyl alcohol

Question 31

common name of 2-propanol

Answer 31

isopropyl alcohol

Question 32

alcohols with 2 hydroxyl groups are called

Answer 32

diols or glycols -diol must number each OH group for diols

Question 33

geminal diols

Answer 33

aka hydrates diols with OH groups on same carbon

Question 34

vicinal diols

Answer 34

diols with OH groups on adjacent carbons

Question 35

IUPAC name C₉H₂₀

Answer 35

nonane

Question 36

IUPAC name C₁₀H₂₂

Answer 36

decane

Question 37

in a molecule with 2 double bonds adjacent to each other and an alcohol, which functional group would take precedence in naming?

Answer 37

alcohol

Question 38

aldehyde nomenclature

Answer 38

-al when higher priority group takes precedence over carbonyl --\> oxo-

Question 39

common name of methanal

Answer 39

formaldehyde

Question 40

common name of ethanal

Answer 40

acetaldehyde

Question 41

common name of propanal

Answer 41

propionaldehyde

Question 42

ketone nomeclature

Answer 42

-one when higher priority group takes precedence over carbonyl --\> oxo-, keto-

Question 43

common name of propanone

Answer 43

acetone

Question 44

For a molecule with a double bond, an aldehyde, and an alcohol, which functional group would determine the suffix when naming?

Answer 44

Ketones and aldehydes both take precedence over both alcohols and hydrocarbon chains, and the functional group that is the highest priority determines the suffix. Because the aldehyde is chain-terminating and therefore on carbon number 1, the aldehyde would determine the suffix when naming this compound.

Question 45

carboxylic acid structure

Answer 45

carbonyl and hydroxyl group on terminal carbon most oxidized functional group --\> highest priority functional group

Question 46

carboxylic acid nomeclature

Answer 46

-oic acid

Question 47

common name for methanoic acid

Answer 47

formic acid

Question 48

common name for ethanoic acid

Answer 48

acetic acid

Question 49

common name for propanoic acid

Answer 49

propionic acid

Question 50

ester structure

Answer 50

carboxylic acid derivative OH replaced with OR

Question 51

ester nomeclature

Answer 51

-oate

Question 52

amide structure

Answer 52

carboxylic acid derivative OH replaced by amino group

Question 53

amide nomenclature

Answer 53

-amide subs attached to nitrogen atom labeled with a N- --\> indicates that group is bonded to parent molecule via nitrogen atom

Question 54

anhydride structure

Answer 54

derivative of carboxylic acid

Question 55

anhydride nomenclature

Answer 55

replace acid with anhydride

Question 56

Answer 56