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Carboxylic Acids Nitriles (CHEM 202), Exercises of Organic Chemistry

Chem 202 Chapter 20 Carboxylic Acids and Nitriles. Naming, Substituent Effects on Acidity & Reactions of Carboxylic Acids. 1. Name the following molecules ...

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Chem 202
Worksheet
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.
b.
c.
d.
2. Rank the following compounds from least acidic to most acidic.
OH
O
OH
O
OH
O
OH
O
HO
O
COOH COOH COOH
ABC
NO2OCH3
pf3
pf4
pf5
pf8

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Chem 202

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.

b.

c.

d.

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

OH

O

OH

O

OH

O

OH

O

HO

O

COOH

COOH COOH

A B

C

NO 2

OCH 3

Chem 202

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

O OH

Cl

O

H

O

HO

OH

HO

H O

HO

OH

O

Chem 202

H 3 C

OH

O

CH

3

O

Ph

OH

O

Chem 202

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.

a.

b.

c.

d.

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

OH

O

In order to name a carboxylic acid,

we substitute -ane with -oic acid

butanoic acid

OH

O

E -4-methyl-hex-3-enoic acid

We start by finding the longest chain and determine

carbon our substituent is on.

Then we determine whether the double has a Z- or E-

configuration

OH

O

benzoic acid

Although we woudl name it using IUPAC rules,

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’

OH

O

HO

O

hexanedioic acid

We determine the longest chain and

since there are two carboxylic groups

we simply add -dioic acid

COOH COOH COOH

A B

C

NO

2 OCH 3

C B A

Acidity of carboxylic acids is determined by how

stable the negative on its oxygen will be. Adding

an electron donating group would destabilize

the charge. On the other hand, an electron

withdrawing group would stabilize the negative

charge as it pulls the negative towards it

via resonance.

Chem 202

NH

2

  1. NBS/ hv
    1. NaCN
    2. LiAlH 4

Br N

Undergoes a Free Radical Substitution

to the most stable radical position.

Br

O

  1. Na
  • — CN

N

2. CH

3

CH

2

MgBr

3. H 3 O

  1. and 3.

MgBr

O

  1. NBS/ hv
  2. NaCN
  3. PhCH 2

MgBr

4. H 3 O

Br

N

BrMg

  1. and 4.

Chem 202

H 3 C

OH

O

CH 3

  1. NBS hv
  2. NaCN

4. H 3 O

Cl AlCl 3

Br C N

2. FRS

  1. Hydrolysis of a

Nitrile group into a

Carboxylic Acid

O

Ph

OH

  1. PhMgBr, ether^ O

2. H 3 O

  1. PBr 3
  2. NaCN

5. H 3 O

O

Ph MgBr

Ph

OH

  1. and 2. Ph

Br

Ph

C

N