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What is the product obtained when neopentyl bromide undergoes the Wurtz reaction?

1. 2,2,4,4-tetramethylhexane
2. 2,2,4,4-tetramethylpentane
3. 2,2,5,5-tetramethylhexane
4. 2,2,3,3-tetramethylhexane

Correct answer: 2,2,5,5-tetramethylhexane

Solution

Wurtz coupling of neopentyl bromide (CH3)3CCH2Br gives (CH3)3C-CH2-CH2-C(CH3)3 = 2,2,5,5-tetramethylhexane, not 2,2,4,4-tetramethylpentane.

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