Question

Product formed in the reaction is:

Answer 1

The given compound is a primary alcohol, it is reacting with $\text{PC}{{\text{l}}_{\text{3}}}$. Phosphorus trichloride ($\text{PC}{{\text{l}}_{\text{3}}}$) is a colourless liquid. In this reaction the $\text{(-OH)}$ group of alcohol is replaced by the $\text{(-Cl)}$ group of phosphorus trichloride.
- On reacting with the chlorine derivative of alcohol gives substitution reaction with the sodium methoxide.
- Lesser the steric hindrance faster will be the rate of bimolecular substitution reaction $\text{(}{{\text{S}}_{\text{N}}}\text{2)}$. $\text{(}{{\text{S}}_{\text{N}}}\text{2)}$ Prefers the less hindered side to attack. So ease of $\text{(}{{\text{S}}_{\text{N}}}\text{2)}$ reaction is $\text{(}{{\text{1}}^{\circ }}\text{}\,{{\text{2}}^{\circ }}\text{}\,{{\text{3}}^{\circ }}\text{)}$.
$\text{(}{{\text{S}}_{\text{N}}}\text{2)}$ Reactions involve inversion of configuration of compound stereochemically. So ${{1}^{\circ }}$ alkyl halide is preferred to $\text{(}{{\text{S}}_{\text{N}}}\text{2)}$ reaction.

Complete step by step answer:
This reaction is completed in two steps-
$\text{PC}{{\text{l}}_{\text{3}}}$ (Phosphorus trichloride) is good chlorinating agent; it reacts quickly with alcohols and performs substitution reaction.
- In the first step chlorination of substrate takes place in which hydroxyl group of substrate compound is replaced by chlorine atom. This reaction is represented through following chemical reaction-

In the second step the chlorinated product of alcohol treated with sodium methoxide in the strong basic medium $\text{(NaOH)}$ . Since chlorine is a poor leaving group, in the presence of polar solvent it gives bimolecular substitution reaction and forms ether. This reaction is represented through the following chemical equation.

Note: - Sterically unhindered primary alkyl haloalkane mainly gives nucleophilic substitution reaction, while sterically hindered (branched primary, secondary and tertiary haloalkane mainly gives elimination reaction.
- Sterically unhindered nucleophiles mainly give substitution reactions. Branched or bulky substrate mainly gives a unimolecular substitution reaction $\text{(}{{\text{S}}_{\text{N}}}\text{1)}$.