Engineering
Chemistry
Test of Alkenes and alkynes
Question

Neopentyl bromide, undergoes dehydrohalogenaton to give alkenes even though it has no hydrogen. This is due to :

E1 mechanism

Rearrangement of carbocations by E1 mechanism

E1CB mechanism

E1 mechanism

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Solution
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Neopentyl bromide gives a carbocation as an intermediate which undergoes for rearrangement and shows a E1 mechanism (even has no β-H atom).
Thus rearrangement of carbocations by E1 mechanism is the correct option.

Reactions happening under E1 mechanism will yield rearranged products due to shift of atoms or groups leading to more stable carbocations. Neopentyl bromide in a solvent ethanol or formic acid (ionizing solvent) undergoes E1 reaction producing

(CH3)2C = CHCH3

The Mechanism is

Wherever possible, rearrangements happen due to higher stability of secondary or tertiary carbocations. Methyl shift takes place in this example.

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