230k views
0 votes
I cannot find a way to start this reaction. For the end, I found that a H that is attached to C with OTs group will be deprotonated forming double bond but before that I think I need to break C-C bond of ketone. Can someone help me on writing the mechanism of this reaction? Thank you.

User Sampada
by
7.8k points

1 Answer

2 votes

Final answer:

The mechanism for the reaction likely involves nucleophilic addition to the ketone's carbonyl group, forming an intermediate which then undergoes deprotonation to form a double bond, implying an elimination reaction. No C-C bond breaking is necessary in the ketone reduction steps and alcohols can be oxidized into ketones.

Step-by-step explanation:

The mechanism involved in the transformation described starts with the nucleophilic addition of a hydride to the electrophilic carbon of a ketone. This step is generally facilitated by a strong nucleophile or a reducing agent. After the initial addition of the hydride ion, a tetrahedral intermediate is formed, which may then undergo various pathways depending on the conditions and the presence of other substituents. The deprotonation of a hydroxyl group attached to the carbon with the leaving group (OTs) indicates that an elimination reaction may be taking place to form a double bond.

For instance, in the reduction of ketones to secondary alcohols, the carbonyl group is targeted by the nucleophile, which can be a hydride donor. No C-C bond breaking is required in this typical reduction process. However, if we are speaking of an elimination reaction, such as the E2 mechanism, a base would abstract a proton from a carbon adjacent to the one bearing the electronegative leaving group, resulting in a double bond formation

Oxidation and reductions are essential transformations in organic chemistry. When dealing with secondary alcohols, an oxidation reaction would typically convert the alcohol into a ketone, as the secondary alcohol has a hydrogen atom attached to the carbonyl group. However, further oxidation of the ketone is not feasible under mild conditions because ketones lack the necessary hydrogen atom at the carbonyl position.

User Zahida
by
7.7k points