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What is the major product obtained from ...

What is the major product obtained from the following reactions ?
`HOCH_(2)overset(O)overset(||)(C)OH overset(SOCl_(2))to overset(CH_(3)OH)to`

A

`HOCH_(2)COOCH_(3)`

B

`CH_(3)OCH_(2)COOCH_(3)`

C

`ClCH_(2)COOCH_(3)`

D

`CH_(3)COCH_(2)COOH`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the major product from the given reactions, let's break down the steps involved in the reaction systematically. ### Step 1: Identify the Starting Compound The starting compound is a carbonyl compound with the following structure: - Hydroxymethyl group (HOCH₂) - A carbonyl group (C=O) - A hydroxyl group (OH) This compound can be represented as HOCH₂-C(=O)-OH. ### Step 2: Reaction with SOCl₂ When the compound reacts with thionyl chloride (SOCl₂), the hydroxyl (OH) groups will be converted to chlorides (Cl). The reaction can be summarized as follows: - The hydroxyl group (OH) on the carbonyl compound is replaced by a chlorine atom (Cl). After this reaction, the structure will be: - HOCH₂-C(=O)-Cl ### Step 3: Nucleophilic Attack by Methanol Next, methanol (CH₃OH) acts as a nucleophile. The oxygen in methanol has a lone pair of electrons, which can attack the electrophilic carbonyl carbon (C=O) in the compound formed in Step 2. The nucleophilic attack can be represented as: - CH₃OH attacks the carbonyl carbon, leading to the formation of a tetrahedral intermediate. ### Step 4: Elimination of Chloride Ion In the tetrahedral intermediate, the chlorine atom (Cl) is a good leaving group. Thus, it can leave, resulting in the formation of an ester. The reaction can be summarized as follows: - The tetrahedral intermediate collapses, and the chloride ion (Cl⁻) is expelled. ### Step 5: Formation of the Ester Product After the elimination of the chloride ion, the final product is an ester. The structure of the ester formed will be: - CH₃-O-C(=O)-CH₂OH This can be simplified to: - CH₃O-C(=O)-CH₂OH, which is methyl 2-hydroxypropanoate. ### Final Product The major product obtained from the reaction is: - Methyl 2-hydroxypropanoate. ### Summary of Steps: 1. Identify the starting compound. 2. React with SOCl₂ to convert OH to Cl. 3. Nucleophilic attack by methanol (CH₃OH). 4. Elimination of chloride ion (Cl⁻). 5. Formation of the ester product.
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Knowledge Check

  • Which of the major product of the following reaction? CH_(3)-overset(O)overset(||)(C)-CI overset(H_(2)S)rarr product

    A
    `CH_(3)-overset(OH)overset(|)underset(SH)underset(|)(C)-CI`
    B
    `CH_(3)-overset(O)overset(||)(C)-SH`
    C
    `CH_(3)-overset(S)overset(||)(C)-CI`
    D
    `CH_(3)-overset(O)overset(||)(C)-S-overset(O)overset(||)(C)-CH_(3)`
  • The major product of the following reaction is CH_(3)-CH=CH-overset(O)overset(||)C-O-CH_(3)overset(LiAlH_(4))rarr

    A
    `CH_(3)-CH=CH-CH_(2)-OH`
    B
    `CH_(3)-CH_(2)-CH_(2)-CH_(2)-OH`
    C
    `CH_(3)-CH_(2)-CH_(2)-CO_(2)-CH_(3)`
    D
    `CH_(3)CH_(2)CH_(2)CHO`
  • What is the major product formed in the reaction? CH_(3)-overset(O)overset(||)(C)-O-overset(O)overset(||)(C)-CF_(3)+C_(2)H_(5)Onaoverset(C_(2)H_(5)OH)to

    A
    `CH_(3)COOC_(2)H_(5)`
    B
    `CF_(3)COOC_(2)H_(5)`
    C
    Both (a) and (b) are formed in comparable amount
    D
    Neither (a) nor (b) is formed as the major product
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