Chapter 11, Problem 11.27P

Interpretation Introduction

(a)

Interpretation:

The reaction and complete, detailed mechanism for the reaction is to be drawn.

Concept introduction:

Alkyl halide is the product of the electrophilic addition reaction of the alkene with a strong Bronsted acid such as $\text{HCl}$ or $\text{HBr}$.

A strong Bronsted acid such as $\text{HCl}$ or $\text{HBr}$ has an electron poor proton, which is an electrophile. These acids can therefore react with the nonpolar $\text{π}$ bond of an alkene, which is relatively electron rich. An electrophilic addition reaction takes place, in which the Bronsted acid adds across a C=C double bond in two steps. In the first step, the proton adds to one carbon followed by the coordination of halide anion.

Answer to Problem 11.27P

The overall reaction for the given compound is

The complete mechanism for the above reaction is

Explanation of Solution

The structure for the given compound $\text{4-chloro-1, 2-dimethylcyclohexane}$ is

The compound shown above is the alkyl halide compound. This compound is formed by an electrophilic addition reaction of alkene with a strong Bronsted acid $\text{HCl}$, followed by the coordination of halide anion.

The overall reaction for the given compound is

The above reaction completes in two steps. In the first step, the electrophilic addition step, the proton is added to one carbon with C=C bond, forming the carbocation intermediate. The second step is the coordination step in which the nucleophile attacks the carbocation to yield the product.

The complete mechanism for the above reaction is

Conclusion

The reaction and complete, detailed mechanism for the reaction is drawn on the basis of the mechanism of electrophilic addition reaction of alkenes with strong acid.

Interpretation Introduction

(b)

Interpretation:

The reaction and complete, detailed mechanism for the reaction is to be drawn.

Concept introduction:

Alkyl halide is the product of the electrophilic addition reaction of the alkene with a strong Bronsted acid such as $\text{HCl}$ or $\text{HBr}$.

A strong Bronsted acid such as $\text{HCl}$ or $\text{HBr}$ has an electron poor proton, which is an electrophile. These acids can therefore react with the nonpolar $\text{π}$ bond of an alkene, which is relatively electron rich. An electrophilic addition reaction takes place, in which the Bronsted acid adds across a C=C double bond in two steps. In the first step, the proton adds to one carbon followed by the coordination of halide anion.

Answer to Problem 11.27P

The overall reaction for the given compound is

The complete mechanism for the above reaction is

Explanation of Solution

The structure for the given compound $\text{1-chloro-1, 2-dimethylcyclohexane}$ is

The compound shown above is the alkyl halide compound. This compound is formed by an electrophilic addition reaction of an alkene with a strong Bronsted acid $\text{HCl}$ followed by the coordination of halide anion.

The overall reaction for the given compound is

The above reaction completes in two steps. In the first step, the electrophilic addition step, the proton is added to one carbon with C=C bond, forming the carbocation intermediate. The second step is the coordination step in which the nucleophile attacks the carbocation to yield the product.

The complete mechanism for the above reaction is

Conclusion

The reaction and complete, detailed mechanism for the reaction is drawn on the basis of the mechanism of electrophilic addition reaction of alkenes with strong acid.

Interpretation Introduction

(c)

Interpretation:

The reaction and complete, detailed mechanism for the reaction is to be drawn.

Concept introduction:

Alkyl halide is the product of the electrophilic addition reaction of the alkene with a strong Bronsted acid such as $\text{HCl}$ or $\text{HBr}$.

A strong Bronsted acid such as $\text{HCl}$ or $\text{HBr}$ has an electron poor proton, which is an electrophile. These acids can therefore react with the nonpolar $\text{π}$ bond of an alkene, which is relatively electron rich. An electrophilic addition reaction takes place, in which the Bronsted acid adds across a C=C double bond in two steps. In the first step, the proton adds to one carbon followed by the coordination of halide anion.

Answer to Problem 11.27P

The overall reaction for the given compound is

The complete mechanism for the above reaction is

Explanation of Solution

The structure for the given compound $\text{1-bromo-1, 1-diphenylbutane}$ is

The compound shown above is the alkyl halide compound. This compound is formed by an electrophilic addition reaction of alkene with a strong Bronsted acid $\text{HCl}$, followed by the coordination of halide anion.

The overall reaction for the given compound is

The above reaction completes in two steps. In the first step, the electrophilic addition step, the proton added to the internal carbon, forming the the more stable carbocation intermediate, which is tertiary and resonance stabilized. The second step is the coordination step in which the nucleophile attacks the carbocation to yield the product.

The complete mechanism for the above reaction is

Conclusion

The reaction and complete, detailed mechanism for the reaction is drawn on the basis of the mechanism of electrophilic addition reaction of alkenes with strong acid.

Interpretation Introduction

(d)

Interpretation:

The reaction and complete, detailed mechanism for the reaction is to be drawn.

Concept introduction:

Alkyl halide is the product of the electrophilic addition reaction of the alkene with a strong Bronsted acid such as $\text{HCl}$ or $\text{HBr}$.

A strong Bronsted acid such as $\text{HCl}$ or $\text{HBr}$ has an electron poor proton, which is an electrophile. These acids can therefore react with the nonpolar $\text{π}$ bond of an alkene, which is relatively electron rich. An electrophilic addition reaction takes place, in which the Bronsted acid adds across a C=C double bond in two steps. In the first step, the proton adds to one carbon followed by the coordination of halide anion.

Answer to Problem 11.27P

The overall reaction for the given compound is

The complete mechanism for the above reaction is

Explanation of Solution

The structure for the given compound $\text{2, 2-dichloropentane}$ is

The compound shown above is the alkyl halide compound. This compound is formed by an electrophilic addition reaction of alkene with a strong Bronsted acid $\text{HCl}$, followed by the coordination of halide anion.

The overall reaction for the given compound is

The above reaction completes in two steps. In the first step, the electrophilic addition step, the proton is added to the internal carbon, forming the the more stable carbocation intermediate, which is tertiary. The second step is the coordination step in which the nucleophile attacks the carbocation to yield the product.

The complete mechanism for the above reaction is

Conclusion

The reaction and complete, detailed mechanism for the reaction is drawn on the basis of the mechanism of electrophilic addition reaction of alkenes with strong acid.