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Question of 147

Q.(a) Give one example of the Sandmeyer reaction.

(b) Identify Y: (CH3)2CH–Br --Na, dry ether--> Y (Product).
(c) (CH3)2CH–OH → CHI3 — carry out this conversion.
Tripura TbseHigher Secondary (+2 Stage) Examination 2024Subjective· 3mImportance★★★★★
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Concept understanding — Wurtz Reaction

The Wurtz Reaction: Why Sodium Makes Alkanes Grow

Imagine you have two identical building blocks — say, two methyl groups (CH3−CH_3-) — and you want to join them into a longer chain (CH3−CH3CH_3-CH_3). That's the core idea of the Wurtz reaction. You take an alkyl halide (like bromoethane) and treat it with sodium metal in dry ether. The sodium strips away the halogen atoms, and the two alkyl fragments couple together.

The reaction was discovered by Charles-Adolphe Wurtz in 1855, and it was one of the first methods to make carbon-carbon bonds deliberately.

The precise statement

Two molecules of an alkyl halide react with two atoms of sodium metal in anhydrous (dry) ether to give a symmetrical alkane and sodium halide.

2R−X+2Na→dry etherR−R+2NaX2R-X + 2Na \xrightarrow{\text{dry ether}} R-R + 2NaX

Here RR is an alkyl group (methyl, ethyl, propyl, etc.) and XX is a halogen (usually chlorine, bromine, or iodine). The product R−RR-R is always a symmetrical alkane — meaning both halves of the new molecule are identical.

How it actually works (the mechanism)

The reaction proceeds through a free-radical intermediate. Sodium metal donates one electron to the alkyl halide, breaking the C−XC-X bond and generating an alkyl radical (R∙R\bullet) and a sodium halide. Two such radicals then combine to form the R−RR-R bond.

R−X+Na⟶R∙+NaXR-X + Na \longrightarrow R\bullet + NaX

2R∙⟶R−R2R\bullet \longrightarrow R-R

Note

The solvent must be dry ether because water would react violently with sodium metal, destroying the reagent before it can couple the alkyl halides.

A concrete example

Take bromoethane (ethyl bromide) with sodium:

2CH3CH2Br+2Na→dry etherCH3CH2CH2CH3+2NaBr2CH_3CH_2Br + 2Na \xrightarrow{\text{dry ether}} CH_3CH_2CH_2CH_3 + 2NaBr

The product is butane — a symmetrical alkane with four carbons.

The big limitation: unsymmetrical products are a mess

If you try to couple two different alkyl halides, say CH3BrCH_3Br and CH3CH2BrCH_3CH_2Br, you get a mixture of three alkanes:

  • CH3−CH3CH_3-CH_3 (ethane) — from two methyl radicals
  • CH3CH2−CH2CH3CH_3CH_2-CH_2CH_3 (butane) — from two ethyl radicals
  • CH3−CH2CH3CH_3-CH_2CH_3 (propane) — from one methyl and one ethyl radical

This mixture is hard to separate, so the Wurtz reaction is practically useful only when both alkyl halides are identical.

Watch out

Never use the Wurtz reaction to prepare an unsymmetrical alkane from two different alkyl halides — you'll get a hopeless mixture of three products.

Why dry ether? Why sodium? …

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