Question

What products would you obtain from reaction of 1-pentanol with the

following reagents?

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

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

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

(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 ${\mathrm{PBr}}_3$to form 1-bromopentane. The reaction can be given as:

Reaction (a)

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

Reaction (b)

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

Reaction (c)

(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="1663238819716" ${\mathrm{CH}}_2{\mathrm{Cl}}_2$ to form pentanal. The reaction can be given as:

Reaction (d)