24.

E: Amines and Heterocycles (Exercises)

1.
2. Last updated
Jun 3, 2019
3.
o 23.E: Carbonyl Condensation Reactions (Exercises)
 
o 25.E: Biomolecules: Carbohydrates (Exercises)
4. picture_as_pdf
Readability
Cite this page
Donate

These are the homework exercises to accompany the Textmap for McMurry's Organic Chemistry
textbook.

24.0 Unit Preview & Unit Objectives

24.1 Naming Amines
24.2 Structure and Properties of Amines
24.3 Basicity of Amines
24.3 Exercises

Questions

Q24.3.1

Select the more basic amine from each of the following pairs of compounds.

(a)
(b)

(c)

Q24.3.2

The 4-methylbenzylammonium ion has a pKa of 9.51, and the butylammonium ion has a pKa of
10.59. Which is more basic? What's the pKb for each compound?

Solutions

S24.3.1

(a)

(b)

(c)
S24.3.2

The butylammonium is more basic. The pKb for butylammonium is 3.41, the pKb for 4-
methylbenzylammonium is 4.49.

24.4 Basicity of Arylamines

24.5 Biological Amines and the Henderson-
Hasselbalch Equation
24.6 Synthesis of Amines
24.7 Reactions of Amines
24.7 Exercises

Questions

Q24.7.1

Draw the product for a Hoffman elimination for each of the following molecules.

(a)

(b)
(c)

(d)

Q24.7.2

Draw the product of a Hoffman elimination for the following molecule.

Solutions

S24.7.1

(a)
(b)

(c)

(d)

S24.7.2

24.8 Reactions of Arylamines

24.8 Exercises

Questions

Q24.8.1

Propose a synthesis for the following compound via benzene and any amine you may require.
Q24.8.2

Proposes synthesis for each of the following compounds via benzene.

(a) N,N-Diethylaniline

(b) p-Bromoaniline

(c) m-Bromoaniline

(d) 2,4-Diethylaniline

Q24.8.3

Propose a synthesis for each of the following molecules from benzene via the diazonium ion.

(a) p-Chlorobenzoic acid

(b) m-Chlorobenzoic acid

(c) m-Dichlorobenzene

(d) p-Ethylbenzoic acid

(e) 1,2,4-Trichlorobenzene

Solutions
S24.8.1

S24.8.2

(a) 1. HNO3, H2SO4; 2. Zn(Hg), HCl; 3. EtBr

(b) 1. HNO3, H2SO4; 2. Zn(Hg), HCl; 3. (CH3CO)O2; 4. Br2, FeBr3; 5. H2O, NaOH

(c) 1. HNO3, H2SO4; 2. Br2, FeBr3; 3. Zn(Hg), HCl

(d) 1. HNO3, H2SO4; 2. Zn(Hg), HCl; 3. (CH3CO)O2; 4. EtCl, AlCl3; 5. H2O, NaOH

S24.8.3

(a) 1. CH3CH2Cl, AlCl3; 2. HNO3, H2SO4; 3. SnCl2; 4. NaNO2, H2SO4; 5. CuBr; 6. KMnO4, H2O

(b) 1. HNO3, H2SO4; 2. Cl2, FeCl3; 3. SnCl2, H3O+; 4. NaNO2, H2SO4; 5. CuCN; 6. H3O+

(c) 1. HNO3, H2SO4; 2. Cl2, FeCl3; 3. SnCl2; 4. NaNO2, H2SO4; 5. CuCl

(d) 1. CH3CH2Cl, AlCl3: 2. HNO3, H2SO4; 3. SnCl2; 4. NaNO2, H2SO4; 5. CuCN; 6. H3O+

(e) 1. HNO3, H2SO4; 2. H2/PtO2; 3. (CH3CO)2O; 4. 2 Cl2; 5. H2O, NaOH; 6. NaNO2, H2SO4; 7.
CuCl