Chapter 27, Problem 7E

Interpretation Introduction

(a)

Interpretation:

Equation for the substitution reaction of $\text{1-bromobutane}$ with $\text{NaOH}$ should be written.

Concept introduction:

Nucleophilic substitution reaction $\left({\text{S}}_{\text{N}}1\right)$ is a two-step substitution reaction. In the first step removal of the leaving group and formation of the carbocation intermediate occurs. The second step involves the formation of the product by the attack of the incoming nucleophile on the carbocation intermediate. It is a unimolecular substitution reaction. A mixture of both retention and inversion product is obtained as the incoming nucleophile can attack from either side of the carbocation.

Nucleophilic substitution reaction $\left({\text{S}}_{\text{N}}2\right)$ is a single step substitution reaction in which electron rich species substitute leaving group. The attack takes place from the back side of the electrophilic center thus an inversion of the configuration takes place. Also, there is a single transition state because bond breaking and bond making occurs simultaneously.

The order of alkyl halide reactivity towards ${\text{S}}_{\text{N}}2$ is as follows:

$1°>2°>3°$

Primary alkyl halide prefers to undergo ${\text{S}}_{\text{N}}2$ substitution reaction and tertiary alkyl halides essentially prefer ${\text{S}}_{\text{N}}1$ substitution reaction.

Interpretation Introduction

(b)

Interpretation:

Equation for the substitution reaction of $\text{1-bromobutane}$ with ${\text{NH}}_3$ should be written.

Concept introduction:

Nucleophilic substitution reaction $\left({\text{S}}_{\text{N}}1\right)$ is a two-step substitution reaction. In the first step removal of the leaving group and formation of the carbocation intermediate occurs. The second step involves the formation of the product by the attack of the incoming nucleophile on the carbocation intermediate. It is a unimolecular substitution reaction. A mixture of both retention and inversion product is obtained as the incoming nucleophile can attack from either side of the carbocation.

Nucleophilic substitution reaction $\left({\text{S}}_{\text{N}}2\right)$ is a single step substitution reaction in which electron rich species substitute leaving group. The attack takes place from the back side of the electrophilic center thus an inversion of the configuration takes place. Also, there is a single transition state because bond breaking and bond making occurs simultaneously.

The order of alkyl halide reactivity towards ${\text{S}}_{\text{N}}2$ is as follows:

$1°>2°>3°$

Primary alkyl halide prefers to undergo ${\text{S}}_{\text{N}}2$ substitution reaction and tertiary alkyl halides essentially prefer ${\text{S}}_{\text{N}}1$ substitution reaction.

Interpretation Introduction

(c)

Interpretation:

Equation for the substitution reaction of $\text{1-bromobutane}$ with $\text{NaCN}$ should be written.

Concept introduction:

Nucleophilic substitution reaction $\left({\text{S}}_{\text{N}}1\right)$ is a two-step substitution reaction. In the first step removal of the leaving group and formation of the carbocation intermediate occurs. The second step involves the formation of the product by the attack of the incoming nucleophile on the carbocation intermediate. It is a unimolecular substitution reaction. A mixture of both retention and inversion product is obtained as the incoming nucleophile can attack from either side of the carbocation.

Nucleophilic substitution reaction $\left({\text{S}}_{\text{N}}2\right)$ is a single step substitution reaction in which electron rich species substitute leaving group. The attack takes place from the back side of the electrophilic center thus an inversion of the configuration takes place. Also, there is a single transition state because bond breaking and bond making occurs simultaneously.

The order of alkyl halide reactivity towards ${\text{S}}_{\text{N}}2$ is as follows:

$1°>2°>3°$

Primary alkyl halide prefers to undergo ${\text{S}}_{\text{N}}2$ substitution reaction and tertiary alkyl halides essentially prefer ${\text{S}}_{\text{N}}1$ substitution reaction.

Interpretation Introduction

(d)

Interpretation:

Equation for the substitution reaction of $\text{1-bromobutane}$ with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{ONa}$ should be written.

Concept introduction:

Nucleophilic substitution reaction $\left({\text{S}}_{\text{N}}1\right)$ is a two-step substitution reaction. In the first step removal of the leaving group and formation of the carbocation intermediate occurs. The second step involves the formation of the product by the attack of the incoming nucleophile on the carbocation intermediate. It is a unimolecular substitution reaction. A mixture of both retention and inversion product is obtained as the incoming nucleophile can attack from either side of the carbocation.

Nucleophilic substitution reaction $\left({\text{S}}_{\text{N}}2\right)$ is a single step substitution reaction in which electron rich species substitute leaving group. The attack takes place from the back side of the electrophilic center thus an inversion of the configuration takes place. Also, there is a single transition state because bond breaking and bond making occurs simultaneously.

The order of alkyl halide reactivity towards ${\text{S}}_{\text{N}}2$ is as follows:

$1°>2°>3°$

Primary alkyl halide prefers to undergo ${\text{S}}_{\text{N}}2$ substitution reaction and tertiary alkyl halides essentially prefer ${\text{S}}_{\text{N}}1$ substitution reaction.