Cyanohydrins can be made from carbonyl compounds by generating CN– ions from HCN in the
presence of a weak base.
In a similar reaction, –CH2CO2CH3 ions are generated from CH3CO2CH3 by strong bases.
Which compound can be made from an aldehyde and CH3CO2CH3 in the presence of a strong
base?
A CH3CH(OH)CO2CH3
B CH3CO2CH2CH(OH)CH3
C CH3CH2CH(OH)CH2CO2CH3
D (CH3)2C(OH)CH2CO2CH3
Ans: C
I have no idea how to obtain the answer!
Please explainnnn!
Thank you in advance :)
To determine which compound can be made from an aldehyde and CH3CO2CH3 in the presence of a strong base, we need to understand the reaction mechanism and how the different components react with each other.
The reaction involves the use of strong base to generate -CH2CO2CH3 ions from CH3CO2CH3. These ions can then react with an aldehyde to form a product. Let's break down the reaction steps:
1. The strong base deprotonates CH3CO2CH3, resulting in the formation of -CH2CO2CH3 ions:
CH3CO2CH3 + strong base → -CH2CO2CH3 + conjugate base
2. The aldehyde reacts with the -CH2CO2CH3 ions to form a compound. In this step, the -CH2CO2CH3 ions act as a nucleophile, attacking the carbonyl carbon of the aldehyde. This leads to the formation of a carbon-carbon bond and an intermediate compound.
3. The intermediate compound rearranges to give the final product. This rearrangement is driven by the stability of the new compound formed.
Now, let's analyze the options and see which one fits the reaction steps:
A. CH3CH(OH)CO2CH3: This compound contains an alcohol (-OH) group attached to the second carbon atom. However, this compound cannot be formed from the reaction as it does not align with the reaction steps mentioned above.
B. CH3CO2CH2CH(OH)CH3: This compound contains an hydroxyl (-OH) group attached to the third carbon atom. This does align with the reaction steps, as -CH2CO2CH3 ions can act as a nucleophile attacking an aldehyde to form this compound.
C. CH3CH2CH(OH)CH2CO2CH3: This compound contains an alcohol (-OH) group attached to the third carbon atom. It aligns with the reaction steps, as -CH2CO2CH3 ions can act as a nucleophile attacking an aldehyde to form this compound.
D. (CH3)2C(OH)CH2CO2CH3: This compound contains an alcohol (-OH) group attached to the fourth carbon atom. However, it cannot be formed from the reaction as it does not align with the reaction steps mentioned above.
Based on the analysis, the compound that can be made from an aldehyde and CH3CO2CH3 in the presence of a strong base is option C: CH3CH2CH(OH)CH2CO2CH3.
I hope this clarifies the concept and helps you understand how to approach such problems in the future!