Question

Show how you would convert butan-1-ol to the following compounds using tosylate intermediates. You may use whatever additional reagents are needed.

(a)1-bromobutane (b)butan-1-amine, CH₃CH₂CH₂CH₂NH₂

(c)butyl ethyl ether, CH₃CH₂CH₂CH₂OCH₂CH₃ (d)pentannitrile, CH₃CH₂CH₂CH₂CN

Short answer

The hydroxyl group of a specific alcohol makes them polar. These groups can create hydrogen bonds with one another and with several other compounds.

1. 
2. 
3. 
4. 

Step-by-step solution

Alcohols

The hydroxyl group of a specific alcohol makes them polar. These groups can create hydrogen bonds with one another and with several other compounds.

Conversion of alcohols to other compounds

Alcohols can be transformed into tosylates using reagents like tosyl chloride and pyridine. The C-O bond of the particular alcohol is not broken during this transformation. This reaction happens with a retention of configuration.

Converting butan-1-ol to various compounds using tosylate intermediates

(a)The reaction of butan-1-ol with TsCl and pyridine leads to butyl tosylate. The butyl tosylate further reacts with NaBr to generate 1-bromobutane.The reaction can be given as:

Conversion of butan-1-ol to 1-bromobutane

(b) The reaction of butan-1-ol with TsCl and pyridine leads to butyl tosylate. The butyl tosylate further reacts with excess ammonia to generate butan-1-amine.The reaction can be given as:

Conversion of butan-1-ol to butan-1-amine

(c) The reaction of butan-1-ol with TsCl and pyridine leads to butyl tosylate. The butyl tosylate further reacts with NaOCH₂CH₃ generate butyl ethyl ether.The reaction can be given as:

Conversion of butan-1-ol to butyl ethyl ether

(d) The reaction of butan-1-ol with TsCl and pyridine leads to butyl tosylate. The butyl tosylate further reacts with KCN to generate pentannitrile. The reaction can be given as:

Conversion of butan-1-ol to pentannitrile