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
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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