Question

Propose a stepwise synthesis for N-propylbutanamide. using 1-proanol and/or carbon dioxide as your only source of carbon and using any other reagents necessary. Detail how the final product could be identified using a spectroscopic method.

Answer 1

This will involve multiple steps

1) first we will generate an amine from given alcohol by reacting it with NH3.

2) Then we will try to increase number of carbon atoms in the given alcohol and will convert it into a sutiable carboxylic acid.

So we will react the alcohol with HCl to give alkyl halide

The alkyl halide will be reacted with Mg in dry ether to give Grignard's reagent

Grignard's reagent will react with CO2 to give butanoic acid

3) finally the butanoic acid will react with the propyl amind to give the corresponding amide

Or we can also convert the butanoic acid to butanoyl chloride by reacting it with SOCl2 so that it may easily react with amine

propan-1-ol propan-1-amine HCl H2C Mg H2C er g Cl 1-chloropropane Propyl magnesium chloride propan-1-amine CH CH H20 Mg CI carbon dioxide он Propyl magnesium chloride butanoic acid CH H3C NH он CH3 butanoic acid propan-1-amine N-propylbutanamide SOC12 NaOH CH CI butanoyl chloride