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Draw a mechanism (with arrow pushing) of the reaction of 1-Bromohexane with Potassium Tert-butoxide forming their elimination product

Question

Draw a mechanism (with arrow pushing) of the reaction of 1-Bromohexane with Potassium Tert-butoxide forming their elimination product

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Solution

Sure, I can help you with that. Here is a step-by-step explanation of the mechanism for the reaction of 1-Bromohexane with Potassium Tert-butoxide to form the elimination product:

Step 1: Deprotonation The first step involves the deprotonation of the tert-butoxide ion (CH3)3CO- by the strong base, potassium tert-butoxide (K+(CH3)3CO-). This results in the formation of the tert-butoxide anion (CH3)3CO-.

Step 2: Nucleophilic attack The tert-butoxide anion acts as a nucleophile and attacks the carbon atom of the 1-bromohexane molecule. The lone pair of electrons on the oxygen atom of the tert-butoxide anion attacks the carbon atom bonded to the bromine atom, resulting in the formation of a new carbon-oxygen bond.

Step 3: Bromide ion departure As the nucleophilic attack occurs, the bromine atom becomes negatively charged. This leads to the departure of the bromide ion (Br-) as a leaving group.

Step 4: Formation of the double bond The departure of the bromide ion results in the formation of a carbocation intermediate. The adjacent carbon atom, which is now positively charged, undergoes a rearrangement to form a more stable carbocation. This rearrangement involves the shifting of a hydrogen atom from a neighboring carbon atom to the carbon atom bearing the positive charge.

Step 5: Deprotonation and elimination In the final step, a base (such as water or another molecule of tert-butoxide) deprotonates the carbon atom adjacent to the carbocation. This deprotonation leads to the formation of a double bond between the two adjacent carbon atoms, resulting in the elimination of a molecule of hydrogen bromide (HBr).

Overall, the reaction of 1-Bromohexane with Potassium Tert-butoxide involves the deprotonation of the tert-butoxide ion, nucleophilic attack, departure of the bromide ion, formation of a carbocation intermediate, and finally, deprotonation and elimination to form the elimination product.

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