Question

What products would you obtain from reaction of 1-pentanol with thefollowing reagents?

(a)${\mathbf{PBr}}_{\mathbf{3}}$

(b) ${\mathbf{SOCl}}_{\mathbf{2}}$

(c) ${\mathbf{CrO}}_{\mathbf{3}}\mathbf{}\mathbf{,}\mathbf{}{\mathbf{H}}_{\mathbf{2}}\mathbf{O}\mathbf{}\mathbf{,}\mathbf{}{\mathbf{H}}_{\mathbf{2}}{\mathbf{SO}}_{\mathbf{4}}$

(d) Dess- Martin periodinane

Short answer

(a)

(b)

(c)

(d)

Step-by-step solution

Reaction of alcohols with PBr3 , SOCl2, CrO3and Dess-Martim periodinate

The reaction of alcohols with ${\mathbf{PBr}}_{\mathbf{3}}$produces the corresponding bromides. Alcohols produce the corresponding chlorides when reacted with ${\mathbf{SOCl}}_{\mathbf{2}}$.Primary alcohols are oxidized into carboxylic acids and secondary alcohols are oxidized into ketones in the presence of ${\mathbf{CrO}}_{\mathbf{3}}$.

Product obtained by the reaction of pentanol with several reagents

(a)The reaction of alcohol with ${\mathrm{PBr}}_3$generates the corresponding bromide. The compound 1-pentanol reacts with localid="1656411988612" ${\mathrm{PBr}}_3$ to form 1-bromopentane. The reaction can be given as:

Reaction (a)

(b)The reaction of alcohol with localid="1656412005713" ${\mathrm{SOCl}}_2$ produces the corresponding chloride. The compound, 1-pentanol reacts with localid="1656412013553" ${\mathrm{SOCl}}_2$ to form 1-chloropentane. The reaction can be given as:

Reaction (b)

(c)The reaction of alcohol with localid="1656412020250" ${\mathrm{CrO}}_3$ and gives carboxylic acids or ketones. The compound, 1-pentanol reacts with localid="1656412026663" ${\mathrm{CrO}}_3$and localid="1656412033864" ${\mathrm{H}}_3{\mathrm{O}}^{+}$ to form pentanoic acid. The reaction can be given as:

(d)The reaction of alcohol with Dess-Martin periodinate produces aldehydes or ketones depending on the alcohol. The compound, 1-pentanol reacts with periodinane and localid="1656412052398" ${\mathrm{CH}}_2{\mathrm{Cl}}_2$ to form pentanal. The reaction can be given as:

Reaction (d)