Question

Predict the expected major product of the following reaction with t-BuOK, t-BuOH:

a) Alcohol
b) Ketone
c) Ester
d) Ether

Answer 1

The expected major product is none of the options given, as tertiary alcohols like t-BuOH do not undergo oxidation to form alcohols, ketones, esters, or ethers with t-BuOK, which is a strong base favoring elimination reactions.

Step-by-step explanation:

The question asks to predict the expected major product of a reaction involving t-BuOK and t-BuOH, and provides options like alcohol, ketone, ester, and ether. Given that t-BuOK is a strong base, it is likely to favor elimination reactions when reacting with halides or alcohols. In the case of t-BuOH, which is a tertiary alcohol, a typical reaction would involve deprotonation of the hydroxyl group leading to the formation of a more stable alkene through an E2 elimination reaction rather than alcohols, ketones, esters, or ethers.

Looking at the options provided, alcohol formation typically occurs from the reduction of aldehydes or ketones, and is not expected here. Ketone formation occurs from the oxidation of secondary alcohols, and this is not applicable as t-BuOH is a tertiary alcohol and thus cannot be oxidized to a ketone. Ester formation is the reaction between an acid and an alcohol, which does not proceed under basic conditions with t-BuOK. Ether formation often involves the reaction between an alkoxide ion and a primary alkyl halide, which is also not indicated in this scenario.

Therefore, the student should predict that no reaction occurs under the specified conditions since tertiary alcohols do not undergo oxidation, and the strong base t-BuOK is not conducive to forming any of the given products with t-BuOH.

Answer 2

The reaction between t-BuOK and t-BuOH would predominantly yield an ether due to Williamson ether synthesis.

The correct option is d.

Step-by-step explanation:

The expected major product of the reaction with t-BuOK and t-BuOH would be ether. t-BuOK (potassium tert-butoxide) is a strong base that is often used to promote ether formation via the reaction of alcohols.

In this case, the tert-butoxide ion (the conjugate base of t-BuOH, or tertiary butanol) will act as a nucleophile and attack another molecule of t-BuOH, leading to the formation of a new C-O-C bond, resulting in the formation of tert-butyl ether.

The reaction is characteristic of the Williamson ether synthesis, where an alkoxide ion reacts with a primary haloalkane or a sulfonate ester to form an ether.

The correct option is d.