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← JEE Advanced 2026 · Paper 1
ChemistryNumerical+4Question 44 of 48

JEE Advanced 2026 · Paper 1, Chemistry question 12

Treatment of buta-1,3-diyne with NaNHX2\ce{NaNH2} (2 equivalents), followed by reaction with excess of trans-CHX3−CH=CH−CHX2−Br\ce{CH3-CH=CH-CH2-Br} gives X as the major product. The maximum number of carbon atoms that are collinear (in a straight line) in X is ____.

Answer and worked solution

Official answer: 6

Product. Two equivalents of NaNHX2\ce{NaNH2} remove both terminal protons of HC≡C−C≡CH\ce{HC#C-C#CH}. The dianion is then alkylated twice by crotyl bromide:
CHX3CH=CHCHX2−C≡C−C≡C−CHX2CH=CHCHX3\ce{CH3CH=CHCH2-C#C-C#C-CH2CH=CHCH3}

Collinear carbons. The four sp carbons lie on a line. Each sp carbon has bond angle 180°, so the two CHX2\ce{CH2} carbons bonded to the ends also lie on that line. The next carbons (=CH\ce{=CH}) are attached at the tetrahedral CHX2\ce{CH2} and leave the line.

Maximum =6=6.