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NEET 2026
Exam
NEET
Year
2026
Subject
Chemistry
Chapter
Hydrocarbons

NEET 2026 · Chemistry · Hydrocarbons

Consider the following reaction sequences and choose the correct...

Consider the following reaction sequences and choose the correct option.
Consider the following reaction sequences and choose the correct option.

Options

  1. AM\text{M} and N\text{N} are stereoisomers
  2. BK\text{K} and L\text{L} are geometrical isomers
  3. CK\text{K} and L\text{L} are enantiomers
  4. DM\text{M} and N\text{N} are geometrical isomers

Correct answer

B. K\text{K} and L\text{L} are geometrical isomers

Step-by-step solution

The given starting material is 1-phenylpropyne, Ph−C≡C−Me\text{Ph}-\text{C}\equiv\text{C}-\text{Me}.

Reduction of the alkyne with H2\text{H}_2 in the presence of Lindlar's catalyst (Pd/C\text{Pd/C} poisoned with BaSO4\text{BaSO}_4 or quinoline) proceeds via syn-addition. This yields the cis-alkene. Therefore, K\text{K} is cis-1-phenylpropene.

Reduction of the alkyne with Na\text{Na} in liquid NH3\text{NH}_3 (Birch reduction conditions) proceeds via anti-addition. This yields the trans-alkene. Therefore, L\text{L} is trans-1-phenylpropene.

Since K\text{K} is the cis-isomer and L\text{L} is the trans-isomer of the same compound, they are geometrical isomers.

Further reactions:
Addition of HBr\text{HBr} to K\text{K} is an electrophilic addition that proceeds via the more stable benzylic carbocation (Ph−C+H−CH2−Me\text{Ph}-\text{C}^+\text{H}-\text{CH}_2-\text{Me}). This gives 1-bromo-1-phenylpropane as product M\text{M}.

Addition of HBr\text{HBr} to L\text{L} in the presence of benzoyl peroxide is a free radical addition (anti-Markovnikov). The bromine radical adds to form the more stable benzylic radical (Ph−C∙H−CH(Br)−Me\text{Ph}-\text{C}^\bullet\text{H}-\text{CH}(\text{Br})-\text{Me}). This gives 2-bromo-1-phenylpropane as product N\text{N}.

M\text{M} and N\text{N} are positional isomers (constitutional isomers), not stereoisomers.

Thus, the only correct statement is that K\text{K} and L\text{L} are geometrical isomers.

Answer: K\text{K} and L\text{L} are geometrical isomers
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