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Chem 202 Chapter 20 Carboxylic Acids and Nitriles

Naming, Substituent Effects on Acidity & Reactions of Carboxylic Acids

1. Name the following molecules using IUPAC rules.

a. OH

OH
b.

OH

c.

O
HO
OH
d. O

2. Rank the following compounds from least acidic to most acidic.

COOH
COOH COOH

NO2
OCH3
A B C

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Propose a synthesis for the following transformation using any reagents you have learned.
3.
Cl O OH

OH H O
O O
HO HO
H HO

4.

OH

O
5.

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NH2

6.

O
Br
7.

O
8.

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H 3C CH3
O

OH
9.

Ph
O O

10. OH

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Chem 202 Chapter 20 Carboxylic Acids and Nitriles KEY
Naming, Substituent Effects on Acidity & Preparing Carboxylic Acids Worksheet

1. Name the following molecules using IUPAC rules.

O
In order to name a carboxylic acid,
OH we substitute -ane with -oic acid

a. butanoic acid

O
5 3 We start by finding the longest chain and determine
6 4 carbon our substituent is on.
1 OH Then we determine whether the double has a Z- or E-
2
configuration
b. E-4-methyl-hex-3-enoic acid

O
Although we woudl name it using IUPAC rules,
OH such as adding carboxylic acid as the parent name,
this compound is an exception as it is more commonly
refered to as its ‘special name’
c. benzoic acid

O
HO We determine the longest chain and
OH since there are two carboxylic groups
O we simply add -dioic acid

d. hexanedioic acid

2. Rank the following compounds from least acidic to most acidic.

COOH COOH COOH

Acidity of carboxylic acids is determined by how

stable the negative on its oxygen will be. Adding
an electron donating group would destabilize
NO2 OCH3 the charge. On the other hand, an electron
withdrawing group would stabilize the negative
A B C charge as it pulls the negative towards it
via resonance.

C B A

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Propose a synthesis for the following transformation using any reagents you have learned.
3.

Cl O OH

1. Na+ —CN

2. H3O+
N
1.
2.
Via hydrolysis of H3O+
the nitrile group is formed
into a carboxylic acid

4.
OH H O
O O
HO HO
H HO
1. Ag2O/ H3O+
2. PCC
3. Ethylene glycol 4.
1.
4. NaBH4/ H3O+
OH O O
O O
HO O
HO H
H O
O
2. O
H 3. The aldehyde is more reactive
therefore the protecting group favors
the aldehyde and not the ketone group

5.

OH
1. NBS/ hv
2. CO2 O
3. H3O+
1. 2. and 3.
Br

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6.

NH2
1. NBS/ hv
2. NaCN
3. LiAlH4 3.
1.
Br N

2.

Undergoes a Free Radical Substitution

to the most stable radical position.

7.

1. Na+ —CN O
Br
2. CH3CH2MgBr
3. H3O+
1. 2. and 3.

MgBr

8.

1. NBS/ hv
2. NaCN O
3. PhCH2MgBr
4. H3O+
1. 3. and 4.
N
Br
BrMg
2.

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9.
H 3C CH3
1. Cl AlCl3 O

2. NBS hv OH
3. NaCN
1. 4. H3O+

4. Hydrolysis of a
Nitrile group into a
Carboxylic Acid

2. FRS

Br 3. C
N

10.
Ph
O 1. PhMgBr, ether O

2. H3O+ OH
3. PBr3
4. NaCN 5.
5. H3O+
Ph
C N
O

Ph MgBr
4.
1. and 2.
Ph Ph
3.
OH Br

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