Chapter 1: Nomenclature

Question 1

5 steps of IUPAC naming:

Answer 1

1. identify the parent chain
2. number the parent chain
3. name the substituents
4. number the substituents
5. complete the name

Question 2

Rules for choosing parent chain

Answer 2

most number of carbons

if tie: choose chain with MORE substituents

Question 3

Rules for numbering the IUPAC parent chain:

Answer 3

always number the chain so that the highest-priority functional group has the lowest possible number

if all substituents have the same priority, number so that they have the lowest possible numbers

Question 4

how is priority determined

Answer 4

the higher the atomic number, the higher the priority

Question 5

How are numbers separated from each other and from words in a compound’s names?

Answer 5

numbers are separated by commas (no spaces)

numbers are separated from words within the compound by hyphens (-)

ex. 3,4-dipropryl-1,3-hexadien-5-yne

Question 6

How are substituents ordered in an IUPAC name?

Answer 6

alphabetical order

do NOT include hyphenated prefixes (di-, tri-, tetra-, n-, tert-) while alphabetizing

DO include non-hyphenated prefixes (iso-, neo-, cyclo-) while alphabetizing

Question 7

hydrocarbons

Answer 7

compounds that contain only carbon and hydrogen atoms

Question 8

Carbon chains w/ single bonds only

Answer 8

alkanes

Question 9

carbon chains w/ double bonds

Answer 9

alkenes

Question 10

carbon chains w/ triple bonds

Answer 10

alkynes

Question 11

Names the first 10 alkanes in order (1-10):

Answer 11

methane, ethane, propane, butane, pentane

hexane, heptane, octane, nonane, decane

Question 12

What is the functional group of an alcohol?

Answer 12

-OH

(hydroxyl)

Question 13

What is the suffix for an alcohol?

Answer 13

• ol
  ex. ethanol

Question 14

Diol

Answer 14

alcohols with 2 hydroxyl groups

Question 15

geminal diols

Answer 15

diols with the two OH groups on the same carbon

(rare - they spontaneously lose a water molecule)

Question 16

vicinal diols

Answer 16

diols with OH groups on adjacent carbons

Question 17

a common name for ethanol:

Answer 17

ethyl alcohol

Question 18

a common name for 2-propanol

Answer 18

isopropyl alcohol

Question 19

carbonyl group

Answer 19

a carbon double bonded to an oxygen

Question 20

aldehydes

Answer 20

the carbonyl is on a terminal carbon that is also attached to a hydrogen

Question 21

aldehyde suffix

Answer 21

• al
  ex. butanal

Question 22

methanal common name + structure

Answer 22

formaldehyde

Question 23

ethanal common name + structure

Answer 23

acetaldehyde

Question 24

propanal common name + structure

Answer 24

propionaldehyde

Question 25

ketones

Answer 25

have a carbonyl group somewhere in the middle of the carbon chain

Question 26

ketone suffix

Answer 26

• one
  ex. 2-propanone

Question 27

the smallest ketone

Answer 27

acetone

Question 28

acetone IUPAC name

Answer 28

2-propanone

Question 29

alpha carbon

Answer 29

the alpha carbon is the carbon adjacent to the carbonyl carbon

Question 30

carboxylic acid

Answer 30

contain both a carbonyl group and a hydroxyl group on a terminal carbon

Question 31

what is the highest-priority (most oxidized) functional group test on the MCAT?

Answer 31

carboxylic acids

note: ONLY CO2 (bonded to 4 O’s) has a more oxidized carbon

Question 32

carboxylic acid suffix

Answer 32

-oic acid

Question 33

methanoic acid common name + structure

Answer 33

formic acid

Question 34

ethanoic acid common name + structure

Answer 34

acetic acid

Question 35

propanoic acid common name + structure

Answer 35

propionic acid

Question 36

carboxylic acid derivatives (3)

Answer 36

esters, amides, anhydrides

Question 37

alkoxy group

Answer 37

Question 38

esters

Answer 38

the -OH group of a carboxylic acid is replaced with an alkoxy group (-OR); R is a hydrocarbon chain

Question 39

ester nomenclature

Answer 39

the first term is the alkyl name of the added R group

the second term is the name of the (original) parent chain with -oate replacing -oic acid

Question 40

amides

Answer 40

the -OH of a carboxylic acid is replaced by an amino group (any Nitrogen containing group)

Question 41

amide suffix

Answer 41

-amide

Question 42

amide nomenclature

Answer 42

substituents attached to the nitrogen atom are prefixes labelled with N- (not numbered)

Question 43

anhydrides

Answer 43

form from 2 carboxylic acid molecules

1 water molecule is removed

many are cyclic

Question 44

anhydride nomenclature

Answer 44

-oic anhydride

if formed from 2 of the same carboxylic acids: the “acid” is replaced with “anhydride”

if formed from 2 different carboxylic acids: both carboxylic acids are named (without “acid”) and anhydride is added to the end

Question 45

list the 10 functional groups in order of decreasing priority:

Answer 45

carboxylic acid, anhydride, ester, amide, aldehyde

ketone, alcohol, alkene, alkyne, alkane

Question 46

carboxylic acid prefix and suffix

Answer 46

prefix: carboxy-
suffix: -oic acid

Question 47

anhydride prefix and suffix

Answer 47

prefix: alkanoyloxycarbonyl-
suffix: anhydride

Question 48

ester prefix and suffix

Answer 48

prefix: alkoxycarbonyl-
suffix: -oate

Question 49

amide prefix and suffix

Answer 49

prefix: carbamoyl- or amido-
suffix: -amide

Question 50

aldehyde prefix and suffix

Answer 50

prefix: oxo-
suffix: -al

Question 51

ketone prefix and suffix

Answer 51

prefix: oxo- or keto-
suffix: -one

Question 52

alcohol prefix and suffix

Answer 52

prefix: hydroxy-
suffix: -ol

Question 53

alkene prefix and suffix

Answer 53

prefix: alkenyl-
suffix: -ene

Question 54

alkyne prefix and suffix

Answer 54

prefix: alkynyl-
suffix: -yne

Question 55

alkane prefix and suffix

Answer 55

prefix: -alkyl
suffix: -ane