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JEE Advanced 2026Paper 1
Exam
JEE Advanced
Year
2026
Paper
Paper 1
Subject
Chemistry
Chapter
Hydrocarbons

JEE Advanced 2026 · Paper 1 · Chemistry · Hydrocarbons

Treatment of buta-1,3-diyne with NaNH_2 ( 2 equivalents), followed...

Treatment of buta-1,3-diyne with NaNH2\text{NaNH}_2 (22 equivalents), followed by reaction with excess of transtrans-CH3-CH=CH-CH2-Br\text{CH}_3\text{-CH=CH-CH}_2\text{-Br} gives X\textbf{X} as the major product. The maximum number of carbon atoms that are collinear (in a straight line) in X\textbf{X} is ____.

Correct answer

0

Step-by-step solution

Buta-1,3-diyne (HC≡C−C≡CHHC \equiv C - C \equiv CH) reacts with 22 equivalents of NaNH2\text{NaNH}_2 to undergo double deprotonation, forming the acetylide dianion:

HC≡C−C≡CH+2NaNH2→ ⊖C≡C−C≡C⊖+2NH3HC \equiv C - C \equiv CH + 2\text{NaNH}_2 \rightarrow \ ^\ominus C \equiv C - C \equiv C ^\ominus + 2\text{NH}_3

This dianion acts as a strong nucleophile and undergoes an SN2S_N2 reaction with the primary allylic halide, transtrans-CH3-CH=CH-CH2-Br\text{CH}_3\text{-CH=CH-CH}_2\text{-Br} (excess ensures both sides react):

⊖C≡C−C≡C⊖+2CH3-CH=CH-CH2-Br→CH3-CH=CH-CH2−C≡C−C≡C−CH2-CH=CH-CH3^\ominus C \equiv C - C \equiv C ^\ominus + 2 \text{CH}_3\text{-CH=CH-CH}_2\text{-Br} \rightarrow \text{CH}_3\text{-CH=CH-CH}_2 - C \equiv C - C \equiv C - \text{CH}_2\text{-CH=CH-CH}_3

In the major product X\textbf{X}, the central diyne unit consists of four spsp hybridized carbon atoms. The geometry around spsp hybridized carbons is linear (bond angle 180∘180^\circ).

The two sp3sp^3 hybridized −CH2−-\text{CH}_2- carbons attached directly to the spsp carbons also lie on this same linear axis. Thus, the sequence of collinear carbon atoms is:

−CH2−C≡C−C≡C−CH2−-\text{CH}_2 - C \equiv C - C \equiv C - \text{CH}_2-

The carbon atoms beyond the −CH2−-\text{CH}_2- groups are attached at a tetrahedral angle (∼109.5∘\sim 109.5^\circ) and are not collinear with the central axis.

Therefore, the maximum number of collinear carbon atoms in X\textbf{X} is 66.

Answer: 66
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