Chapter 1: Nomenclature

Question 1

What is Step 1 of IUPAC naming?

Answer 1

Identify the longest carbon chain with the highest-order functional group

This longest carbon chain will be known as the parent chain

Question 2

If there are 2+ chains of equal length, which chain gets higher priority?

Answer 2

The more substituted chain.

Question 3

What is Step 2 of IUPAC naming?

Answer 3

Number the chain

The carbon marked as #1 is the one closest to the high-priority functional group

If all functional groups have the same priority, the most substituted carbons should get the lowest numbers

Question 4

What is Step 3 of IUPAC naming?

Answer 4

Name the substituents

Functional groups that are NOT part of the parent chain

Question 5

What is the suffix for carbon chain substituents?

Answer 5

“-yl”

Question 6

Draw

t-butyl

common alkyl substituent

Answer 6

Question 7

Draw

isopropyl

common alkyl substituent

Answer 7

Question 8

Draw

isobutyl

common alkyl substituent

Answer 8

Question 9

Draw

sec-butyl

common alkyl substituent

Answer 9

Question 10

What is Step 4 of IUPAC naming?

Answer 10

Assign a number to each substituent

Pair substituents that you have named to the corresponding numbers in the parent chain.

Substituents also get a carbon # designation.
Use di-, tri-, tetra-, etc. to indicate multiple substituents of the same type

Question 11

What is Step 5 of IUPAC naming?

Answer 11

Complete the name

Names of substituents are listed in alphabetical order, with each substituent preceded by its number

Prefixes are ignored while alphabetizing, with the acception of nonhyphenated roots like iso-, neo-, cyclo-, etc.

Question 12

Heteroatom

Answer 12

Atoms besides carbon and hydrogen, e.g. oxygen, nitrogen, phosphorus, or halogens

Question 13

What does it mean to be in a “lower oxidation state”?

Answer 13

Lots of carbon-hydrogen bonds = lower oxidation state, or a more reduced state

Question 14

What does it mean to be in a higher oxidation state?

Answer 14

If it contains a lot of carbon-heteroatom bonds

Question 15

Alkanes

Answer 15

Simple hydrocarbon molecuels with the formula C_nH2n+2

Question 16

What are common substituents on alkanes?

Answer 16

Halogens, e.g. fluoro-, chloro-, bromo-, iodo-

Question 17

Alkenes and alkynes

Answer 17

Alkene = double bond
Alkyne = triple bond

named like substituents

not usually tested on MCAT except for unsaturated fatty acids

Question 18

Which substituent gets the lowest numbered carbon?

Answer 18

The highest priority substituent

Question 19

What is the suffix and functional group called?

Alcohol

Answer 19

suffix “-ol”
-OH = hydroxyl group

Question 20

Which takes priority, alcohol or multiple bonds?

Answer 20

Alcohol, because they are more oxidized.

Question 21

How do you denote an alcohol if it is the highest priority?

Answer 21

“-ol”

Question 22

How do you denote an alcohol if it is NOT the highest priority?

Answer 22

“hydroxy-“

Question 23

Diols

aka “glycol”

Answer 23

Alcohol with 2 hydroxyl groups

Question 24

Geminal diols

Answer 24

2 alcohols on the SAME carbon, aka hydrates

Not very common because they spontaneously dehydrate to produce carbonyl compounds

Question 25

Vicinal Diols

Answer 25

2 alcohols on **ADJACENT** carbons

Question 26

What type of group do aldehydes and ketones contain? ## Footnote C

Answer 26

A carbonyl group (C=O)

Question 27

What is the difference between aldehydes and ketones?

Answer 27

Aldehydes are chain-terminating; ketones are in the middle of the carbon chain

Question 28

# What is the suffix and functional group called? Draw. Aldehydes

Answer 28

Suffix "-al" if at position 1 (which it usually is, so you don't need to number)

Question 29

Draw methanal Common name? ## Footnote common aldehyde

Answer 29

| formal = 1 carbon formaldehyde

Question 30

acetaldehyde | ethanal ## Footnote common aldehyde

Answer 30

| acet = 2 carbons

Question 31

propionaldehyde | propanal ## Footnote common aldehyde

Answer 31

| propion = 3 carbons

Question 32

# What is the suffix and functional group called? Draw. Ketones

Answer 32

suffix "-one" Always have to assign a # to these, since they are always in the middle of a carbone chain

Question 33

What do you call ketones when there is a higher priority group than a carbonyl present in the molecule?

Answer 33

Use the prefix "oxo-"

Question 34

How do you name carbons relative to the carbonyl?

Answer 34

The carbon adjacent to the carbonyl is the "alpha" carbon

Question 35

# What is the suffix and functional group called? Draw. Carboxylic Acids

Answer 35

carbonyl (C=O) + hydroxyl (-OH) on terminal carbon

Question 36

What is more oxidized than a carboxylic acid?

Answer 36

CO_{2, since it has 4 bonds to oxygen}

Question 37

# Draw methanoic acid Common name? ## Footnote common carboxylic acid

Answer 37

| formal = 1 carbon formic acid

Question 38

# Draw ethanoic acid | Common name? ## Footnote common carboxylic acid

Answer 38

| acet = 2 carbons acetic acid

Question 39

# Draw propanoic acid | propionic acid ## Footnote common carboxylic acid

Answer 39

| propion = 3 carbons

Question 40

# How do you name? What is the functional group called? Draw. Esters

Answer 40

Suffix = "-oate" hydroxyl (-OH) is replaced with alkoxy (-OR) group 1st term = alkyl name of esterifying group 2nd term = parent acid

Question 41

# What is the suffix? What is the functional group called? Draw. Amide

Answer 41

hydroxyl replaced by **amino**, the N can be bonded to 0, 1, or 2 alkyl groups Suffix "-amide" Substituents attached to the N are labeled with the prefix "N-"

Question 42

# How do you name? What is the functional group called? Draw. Anhydride

Answer 42

Forms from 2 carboxylic acid molecules, removes 1 H2O Many are cyclic -- > formed from intramolecular dehydration "________ anhydride"

Question 43

# Order by priority, from highest to lowest ketone alkene anhydride carboxylic acid ester alkane amide alkene alcohol aldehyde

Answer 43

carboxylic acid anhydride ester amide aldehyde ketone alcohol alkene = alkyne alkane

Question 44

# What is the prefix and suffix for this functional group? carboxylic acid

Answer 44

Prefix: carboxyl- Suffix: -oic acid

Question 45

# What is the prefix and suffix for this functional group? anhydride

Answer 45

Prefix: alkanoyloxycarbonyl- Suffix: anhydride

Question 46

# What is the prefix and suffix for this functional group? ester

Answer 46

Prefix: alkoxycarbonyl- Suffix: -oate

Question 47

# What is the prefix and suffix for this functional group? amide

Answer 47

Prefix: carbamoyl- or amido- Suffix: -amide

Question 48

# What is the prefix and suffix for this functional group? aldehyde

Answer 48

Prefix: oxo- Suffix: -al

Question 49

# What is the prefix and suffix for this functional group? ketone

Answer 49

Prefix: oxo- or keto- Suffix: -one

Question 50

# What is the prefix and suffix for this functional group? alcohol

Answer 50

Prefix: hydroxyl- Suffix: -ol

Question 51

# What is the prefix and suffix for this functional group? alkene

Answer 51

Prefix: alkenyl- Suffix: -ene

Question 52

# What is the prefix and suffix for this functional group? alkyne

Answer 52

Prefix: alkynl- Suffix: -yne

Question 53

# What is the prefix and suffix for this functional group? alkane

Answer 53

Prefix: alkyl- Suffix: -ane