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CH(3)-underset(Cl)underset(|)(C)H-unders...

`CH_(3)-underset(Cl)underset(|)(C)H-underset(Cl)underset(|)(C)H-CH_(3)underset((ii)NaNH2)overset((i)Alc.KOH)(to)A` (major) `underset(Pd//CaCO_(3))overset(H_(2))(to)B`

A

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

B

`CH_(2)-CH_(2)-CH_(2)-CH_(3)`

C

D

Text Solution

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The correct Answer is:
To solve the given question, we need to follow the steps of the reactions described. Let's break it down step by step. ### Step 1: Identify the Initial Compound The initial compound is given as: \[ \text{CH}_3\text{CCl}(\text{CHCl})\text{CH}_3 \] This compound has two chlorine atoms attached to the carbon chain. ### Step 2: Reaction with Alcoholic KOH The first step involves the reaction of the compound with alcoholic KOH. Since alcoholic KOH is used, it promotes an elimination reaction (dehydrohalogenation). 1. **Elimination Reaction**: - One chlorine atom (Cl) will be removed from the alpha carbon, and a hydrogen atom will be removed from the beta carbon. - This results in the formation of a double bond between the two carbons. The product after this step (let's call it A) will be: \[ \text{CH}_3\text{C}=\text{C}\text{H}\text{CH}_3 \] This represents a compound with a double bond between the two carbons. ### Step 3: Reaction with NaNH2 Next, the product A undergoes a reaction with sodium amide (NaNH2), which acts as a strong base. 2. **Formation of Alkyne**: - NaNH2 will deprotonate the hydrogen adjacent to the double bond, leading to the formation of a triple bond. - The product after this reaction (let's call it B) will be: \[ \text{CH}_3\text{C} \equiv \text{C}\text{CH}_3 \] This is a symmetrical alkyne. ### Step 4: Hydrogenation with Pd/CaCO3 The final step involves the hydrogenation of the alkyne using hydrogen gas (H2) in the presence of palladium on calcium carbonate (Pd/CaCO3), which acts as a Lindlar catalyst. 3. **Reduction of Alkyne to Alkene**: - The alkyne will be partially hydrogenated to form a cis-alkene. - The product after this step (let's call it C) will be: \[ \text{C} \text{H}_3\text{C}=\text{C}\text{H}\text{CH}_3 \] This is a cis-alkene. ### Conclusion Thus, the final products A and B are: - A: \[ \text{CH}_3\text{C} \equiv \text{C}\text{CH}_3 \] (an alkyne) - B: \[ \text{C} \text{H}_3\text{C}=\text{C}\text{H}\text{CH}_3 \] (a cis-alkene) The correct answer to the question is option 3.
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