Why are NH₃ and CH₃NH₂ no longer nucleophiles when they are protonated?

Explain the difference in reactivity between CH₃O⁺H₂ and CH₃OH in a nucleophilic substitution reaction. (The pK_a of H₃O⁺ is −1.7.)

Explain how 1-butanol can be converted into the following compounds:

a.

Explain how 1-butanol can be converted into the following compounds:

b.

What is the major product of each of the following reactions?

a.

What is the major product of each of the following reactions?

b.

What is the major product of each of the following reactions?

c.

What is the major product of each of the following reactions?

d.

What stereoisomers does the following reaction form?

What stereoisomers do the following reactions form?

a.

b.

What stereoisomers do the following reactions form?

c.

d.

What stereoisomers do the following reactions form?

a.

What stereoisomers do the following reactions form?

b.

What stereoisomers do the following reactions form?

c.

What stereoisomers do the following reactions form?

d.

Show how 1-propanol can be converted into the following compounds by means of a sulfonate ester:

a. CH₃CH₂CH₂SCH₂CH₃

Show how 1-propanol can be converted into the following compounds by means of a sulfonate ester:

b.

Which of the following alcohols dehydrates the fastest when heated with acid?

What is the major product obtained when each of the following alcohols is heated in the presence of H₂SO₄?

a.

What is the major product obtained when each of the following alcohols is heated in the presence of H₂SO₄?

b.

Heating an alcohol with sulfuric acid is a good way to prepare a symmetrical ether such as diethyl ether.

a. Explain why it is not a good way to prepare an unsymmetrical ether such as ethyl propyl ether.

Heating an alcohol with sulfuric acid is a good way to prepare a symmetrical ether such as diethyl ether.

b. How would you synthesize ethyl propyl ether?

Propose a mechanism for each of the following reactions:

a.

Explain why the following alcohols, when heated with acid, form the same alkene.

What stereoisomers are formed in the following reactions? Which stereoisomer is the major product?

a. the acid-catalyzed dehydration of 1-pentanol to 2-pentene

What stereoisomers are formed in the following reactions? Which stereoisomer is the major product?

b. the acid-catalyzed dehydration of 3,4-dimethyl-3-hexanol to 3,4-dimethyl-3-hexene

If the compound shown in the margin is heated in the presence of H₂SO₄,

a. what constitutional isomer would be formed in greatest yield?

b. what stereoisomer would be formed in greater yield?

What alcohol would you treat with phosphorus oxychloride and pyridine to form each of the following alkenes?

a.

b.

What product is obtained from the reaction of each of the following alcohols with

a. H₂CrO₄?

1. 3-pentanol

2. 1-pentanol

3. 2-methyl-2-pentanol