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The major product of the following react...

The major product of the following reaction is :
`CH_(3)overset(OH)overset(|)(C)HCH_(2)CH_(2)NH_(2)overset("ethyl formate(1 equiv.)")underset("triethylamine")rarr`

A

`CH_(3)overset(OH)overset(|)(C)H-CH=CH_(2)`

B

`CH_(3)overset(OH)overset(|)(C)HCH_(2)CH_(2)NHCHO`

C

D

`CH_(3)CH=CH-CH_(2)NH_(2)`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the major product of the given reaction, we will analyze the substrate and the reagents step by step. ### Step 1: Identify the Substrate The substrate is given as: \[ \text{CH}_3-\text{C}(\text{OH})(\text{C}_2\text{H}_5)-\text{CH}_2-\text{CH}_2-\text{NH}_2 \] This structure consists of a carbon chain with a hydroxyl group (-OH) and an amine group (-NH2). ### Step 2: Identify the Reagents The reagents provided are: - Ethyl formate (HCOOCH2CH3) - Triethylamine Ethyl formate has the structure: \[ \text{HCOO}-\text{C}_2\text{H}_5 \] It contains a carbonyl group (C=O) and an ethyl group. ### Step 3: Determine the Nucleophile In this reaction, we have two potential nucleophiles: the hydroxyl group (-OH) and the amine group (-NH2). Among these, the amine group is a stronger nucleophile compared to the hydroxyl group. ### Step 4: Nucleophilic Attack The amine group (-NH2) will attack the carbonyl carbon of ethyl formate. This leads to the formation of a tetrahedral intermediate. The reaction can be visualized as follows: 1. The nitrogen atom of the amine attacks the carbonyl carbon of ethyl formate. 2. This results in the opening of the carbonyl bond and formation of a negatively charged oxygen. ### Step 5: Collapse of the Tetrahedral Intermediate After the formation of the tetrahedral intermediate, the negatively charged oxygen will push back to reform the carbonyl double bond, causing the ethoxy group (O-C2H5) to leave. This results in the formation of an imine (or a related structure) and the release of ethanol. ### Step 6: Final Product The final product of the reaction will be: \[ \text{CH}_3-\text{C}(\text{OH})(\text{C}_2\text{H}_2\text{N})-\text{C}(=O)-\text{H} \] This structure represents an aldehyde. ### Conclusion The major product of the reaction is an aldehyde. ### Answer: The correct option is option B (aldehyde). ---
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