Chapter 11.SE, Problem 45AP

Interpretation Introduction

a)

Interpretation:

The given molecule has to be prepared by using nucleophilic substitution reaction.

Concept introduction:

S_N1 reaction:

The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergo S_N1substitution reaction.

S_N2 reaction:

The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid, the bromine atom attacks back side of the carbon atoms in simultaneous manner and which is bearing alcohol group which yield the corresponding product.

Example:

Alcohol is reaction with tosyl chloride in pyridine which provides retention of configuration of tosylated compound. This tosylated compound is further reaction with sodium methoxide which undergoes again S_N2 type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below,

S_N2 reaction is second order reaction, the rate of the reaction is depending on the both substrate and nucleophiles.

Answer to Problem 45AP

The reaction is given below,

Explanation of Solution

Given information:

The product of the reaction is given below,

The reaction is given below,

The sodium amide is acts as a base and it abstract the highly acidic proton from propylene gives carbanion, this carbanion react with 2-bromo propane gives the corresponding product.

Conclusion

The given molecule is prepared by using nucleophilic substitution reaction.

Interpretation Introduction

b)

Interpretation:

The given molecule has to be prepared by using nucleophilic substitution reaction.

Concept introduction:

S_N1 reaction:

The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergo S_N1substitution reaction.

S_N2 reaction:

The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid, the bromine atom attacks back side of the carbon atoms in simultaneous manner and which is bearing alcohol group which yield the corresponding product.

Example:

Alcohol is reaction with tosyl chloride in pyridine which provides retention of configuration of tosylated compound. This tosylated compound is further reaction with sodium methoxide which undergoes again S_N2 type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below,

S_N2 reaction is second order reaction, the rate of the reaction is depending on the both substrate and nucleophiles.

Answer to Problem 45AP

The reaction is given below,

Explanation of Solution

Given information:

The product of the reaction is given below,

The reaction is given below,

The sodium tertiary butoxide is acts as a base and it react with methyl bromide gives the corresponding ether product.

Conclusion

The given molecule is prepared by using nucleophilic substitution reaction.

Interpretation Introduction

c)

Interpretation:

The given molecule has to be prepared by using nucleophilic substitution reaction.

Concept introduction:

S_N1 reaction:

The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergo S_N1substitution reaction.

S_N2 reaction:

The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid, the bromine atom attacks back side of the carbon atoms in simultaneous manner and which is bearing alcohol group which yield the corresponding product.

Example:

Alcohol is reaction with tosyl chloride in pyridine which provides retention of configuration of tosylated compound. This tosylated compound is further reaction with sodium methoxide which undergoes again S_N2 type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below,

S_N2 reaction is second order reaction, the rate of the reaction is depending on the both substrate and nucleophiles.

Answer to Problem 45AP

The reaction is given below,

Explanation of Solution

Given information:

The product of the reaction is given below,

The reaction is given below,

n-butyl bromide undergoes nucleophilic substitution reaction with cyanide (sodium cyanide) gives the corresponding cyanide product.

Conclusion

The given molecule is prepared by using nucleophilic substitution reaction.

Interpretation Introduction

d)

Interpretation:

The given molecule has to be prepared by using nucleophilic substitution reaction.

Concept introduction:

S_N1 reaction:

The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergo S_N1substitution reaction.

S_N2 reaction:

The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid, the bromine atom attacks back side of the carbon atoms in simultaneous manner and which is bearing alcohol group which yield the corresponding product.

Example:

Alcohol is reaction with tosyl chloride in pyridine which provides retention of configuration of tosylated compound. This tosylated compound is further reaction with sodium methoxide which undergoes again S_N2 type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below,

S_N2 reaction is second order reaction, the rate of the reaction is depending on the both substrate and nucleophiles.

Answer to Problem 45AP

The reaction is given below,

Explanation of Solution

Given information:

The reaction is given below,

The reaction is given below,

Ethyl bromide undergoes nucleophilic substitution reaction with cyanide (sodium cyanide) gives the corresponding cyanide product, this cyanide undergoes catalytic reduction using Pt (metal reduction) gives amine compound.

Conclusion

The given molecule is prepared by using nucleophilic substitution reaction.