Question

Draw the structures of major products: (a) Chlorobenzene + $CH_3Cl$ / Na, dry ether
(b) p-Hydroxyphenethyl alcohol + HBr

Hint:

Wurtz-Fittig: ArX + RX + 2Na ? Ar-R + 2NaX. In (b), alcoholic $-$OH reacts with HBr but phenolic $-$OH does not under mild conditions.

Answer 1

Step 1: Reaction (a) — Wurtz-Fittig.
Chlorobenzene ($C_6H_5Cl$) + $CH_3Cl$ with Na metal in dry ether. This is the Wurtz-Fittig reaction: the aryl and alkyl halides couple by loss of both halides as NaCl, joining the aryl and methyl groups with a new C-C bond.
Step 2: Product of (a).
$C_6H_5Cl + CH_3Cl \xrightarrow{Na,\text{ dry ether}} C_6H_5-CH_3 + 2NaCl$. Product: Toluene ($C_6H_5CH_3$).
Step 3: Reaction (b) — HBr with p-hydroxyphenethyl alcohol.
Compound: $HO-C_6H_4-CH_2CH_2OH$ (para). HBr preferentially substitutes the primary aliphatic $-OH$ (more reactive than phenolic $-OH$). Product: $HO-C_6H_4-CH_2CH_2Br$ (p-hydroxyphenethyl bromide).
Step 4: Summary of products.
(a) Toluene: $C_6H_5CH_3$; (b) p-Hydroxyphenethyl bromide: $HO-C_6H_4-CH_2CH_2Br$.