JEE Advanced · 2008 · 13 Apr 2008 · Paper 1 · Haloalkanes and Haloarenes

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In the following reaction sequence, products I, J and L are formed. K represents a reagent.

The structures of compounds and , respectively, are
  1. (A)(see structure) and
    ✓ Correct
  2. (B)(see structure) and
  3. (C)(see structure) and
  4. (D)(see structure) and

Answer: (A)

Solution

Compound I (6-bromohex-3-yne) undergoes Grignard reaction:
  1. Formation of Grignard reagent with Mg/ether
  2. Reaction with
  3. Hydrolysis with

This produces hex-3-ynoic acid, which is compound J.

To convert the carboxylic acid to an acid chloride (for the next step), thionyl chloride () is used as reagent K.

Therefore, option (A) is correct.

JEE Advanced · 2008 · 13 Apr 2008 · Paper 1 · Single correct option

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