Chapter 16, Problem 64P

a.

Interpretation Introduction

Interpretation:

Thiols can be prepared from the reaction of thiourea with an alkyl halide , followed by hydroxide –io-promoted hydrolysis.  Propose a mechanism for the reaction

Concept introduction:

Organosulfur compound that contains a carbon –bonded sulfhydry group are called thiols. It has strong odour. The –SH froup is called a mercapto group. Named by adding the suffix –thiol to the alkane name. They are commonly prepared by an ${\text{S}}_{\text{N}}\text{2}$ reaction.

For example, the structure of 2-methyl propane 2-thiol.

b.

Interpretation Introduction

Interpretation:

Thiols can be prepared from the reaction of thiourea with an alkyl halide , followed by hydroxide –io-promoted hydrolysis.  What will be formed if the alkyl halide employed is pentyl bromide.

            

Concept introduction:

Organosulfur compound that contains a carbon –bonded sulfhydry group are called thiols. It has strong odour. The –SH froup is called a mercapto group. Named by adding the suffix –thiol to the alkane name. They are commonly prepared by an ${\text{S}}_{\text{N}}\text{2}$ reaction.

For example, the structure of 2-methyl propane 2-thiol.