Chapter 17, Problem 17.69EP

(a)

Interpretation Introduction

Interpretation:

Structure of amine or quaternary ammonium salt that is obtained when trimethylamine and ethyl bromide is reacted in presence of strong base has to be drawn.

Concept Introduction:

Alkylation reaction is a reaction in which the transfer of alkyl group from one molecule to another molecule takes place.  While considering amines, the alkylating agent that is used is alkyl halides.  Alkylation is done under basic conditions.  The general equations for amines alkylation process is,

  $\begin{array}{l}\text{Ammonia}\text{+}\text{Alkyl}\text{halide}\stackrel{\text{Base}}{\to }\text{1°}\text{amine}\\ \text{1°}\text{amine}\text{+}\text{Alkyl}\text{halide}\stackrel{\text{Base}}{\to }\text{2°}\text{amine}\\ \text{2°}\text{amine}\text{+}\text{Alkyl}\text{halide}\stackrel{\text{Base}}{\to }\text{3°}\text{amine}\\ \text{3°}\text{amine}\text{+}\text{Alkyl}\text{halide}\stackrel{\text{Base}}{\to }\text{quaternary ammonium salt}\end{array}$

Answer to Problem 17.69EP

The structure of product obtained is,

Explanation of Solution

Given reactants are trimethylamine and ethyl bromide.  In this, the amine given is a tertiary amine.  When tertiary amine is treated with an alkyl halide, the product obtained is a quaternary ammonium salt.  The complete reaction and the structure of the product formed is given as,

Conclusion

Structure of the product formed is drawn.

(b)

Interpretation Introduction

Interpretation:

Structure of amine or quaternary ammonium salt that is obtained when diisopropylamine and methyl bromide is reacted in presence of strong base has to be drawn.

Concept Introduction:

Alkylation reaction is a reaction in which the transfer of alkyl group from one molecule to another molecule takes place.  While considering amines, the alkylating agent that is used is alkyl halides.  Alkylation is done under basic conditions.  The general equations for amines alkylation process is,

  $\begin{array}{l}\text{Ammonia}\text{+}\text{Alkyl}\text{halide}\stackrel{\text{Base}}{\to }\text{1°}\text{amine}\\ \text{1°}\text{amine}\text{+}\text{Alkyl}\text{halide}\stackrel{\text{Base}}{\to }\text{2°}\text{amine}\\ \text{2°}\text{amine}\text{+}\text{Alkyl}\text{halide}\stackrel{\text{Base}}{\to }\text{3°}\text{amine}\\ \text{3°}\text{amine}\text{+}\text{Alkyl}\text{halide}\stackrel{\text{Base}}{\to }\text{quaternary ammonium salt}\end{array}$

Answer to Problem 17.69EP

The structure of product obtained is,

Explanation of Solution

Given reactants are diisopropylamine and methyl bromide.  In this, the amine given is a secondary amine.  When secondary amine is treated with an alkyl halide, the product obtained is a tertiary amine.  The complete reaction and the structure of the product formed is given as,

Conclusion

Structure of the product formed is drawn.

(c)

Interpretation Introduction

Interpretation:

Structure of amine or quaternary ammonium salt that is obtained when ethylmethylpropylamine and methyl chloride is reacted in presence of strong base has to be drawn.

Concept Introduction:

Alkylation reaction is a reaction in which the transfer of alkyl group from one molecule to another molecule takes place.  While considering amines, the alkylating agent that is used is alkyl halides.  Alkylation is done under basic conditions.  The general equations for amines alkylation process is,

  $\begin{array}{l}\text{Ammonia}\text{+}\text{Alkyl}\text{halide}\stackrel{\text{Base}}{\to }\text{1°}\text{amine}\\ \text{1°}\text{amine}\text{+}\text{Alkyl}\text{halide}\stackrel{\text{Base}}{\to }\text{2°}\text{amine}\\ \text{2°}\text{amine}\text{+}\text{Alkyl}\text{halide}\stackrel{\text{Base}}{\to }\text{3°}\text{amine}\\ \text{3°}\text{amine}\text{+}\text{Alkyl}\text{halide}\stackrel{\text{Base}}{\to }\text{quaternary ammonium salt}\end{array}$

Answer to Problem 17.69EP

The structure of product obtained is,

Explanation of Solution

Given reactants are ethylmethylpropylamine and methyl chloride.  In this, the amine given is a tertiary amine.  When tertiary amine is treated with an alkyl halide, the product obtained is a quaternary ammonium salt.  The complete reaction and the structure of the product formed is given as,

Conclusion

Structure of the product formed is drawn.

(d)

Interpretation Introduction

Interpretation:

Structure of amine or quaternary ammonium salt that is obtained when ethylamine and ethyl chloride is reacted in presence of strong base has to be drawn.

Concept Introduction:

Alkylation reaction is a reaction in which the transfer of alkyl group from one molecule to another molecule takes place.  While considering amines, the alkylating agent that is used is alkyl halides.  Alkylation is done under basic conditions.  The general equations for amines alkylation process is,

  $\begin{array}{l}\text{Ammonia}\text{+}\text{Alkyl}\text{halide}\stackrel{\text{Base}}{\to }\text{1°}\text{amine}\\ \text{1°}\text{amine}\text{+}\text{Alkyl}\text{halide}\stackrel{\text{Base}}{\to }\text{2°}\text{amine}\\ \text{2°}\text{amine}\text{+}\text{Alkyl}\text{halide}\stackrel{\text{Base}}{\to }\text{3°}\text{amine}\\ \text{3°}\text{amine}\text{+}\text{Alkyl}\text{halide}\stackrel{\text{Base}}{\to }\text{quaternary ammonium salt}\end{array}$

Answer to Problem 17.69EP

The structure of product obtained is,

Explanation of Solution

Given reactants are ethylamine and ethyl chloride.  In this, the amine given is a primary amine.  When primary amine is treated with an alkyl halide, the product obtained is a secondary amine.  The complete reaction and the structure of the product formed is given as,

Conclusion

Structure of the product formed is drawn.