Open Question
Predict the mechanism for the following reactions. Provide the full mechanism and draw the final product.
8. Elimination Reactions
Cumulative Substitution/Elimination
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Predict the major, organic product for the following reaction.
A
B
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D
Verified step by step guidance1
Identify the type of reaction: The reaction involves NaOtBu (sodium tert-butoxide) in tBuOH (tert-butanol), which suggests an E2 elimination reaction due to the strong, bulky base.
Locate the leaving group: The chlorine (Cl) atom is the leaving group attached to the chiral carbon in the starting material.
Determine the β-hydrogens: Identify the β-hydrogens on the carbon atoms adjacent to the carbon bearing the leaving group. These are the hydrogens that can be abstracted by the base.
Consider Zaitsev's rule: In E2 eliminations, the more substituted alkene is generally favored. However, with a bulky base like NaOtBu, the less substituted alkene (Hofmann product) may be favored due to steric hindrance.
Predict the major product: Based on the steric hindrance and the base used, predict the formation of the less substituted alkene as the major product, where the double bond forms between the carbon bearing the leaving group and the less hindered β-carbon.
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