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Consider the following reaction: CH(3)...

Consider the following reaction:
`CH_(3)underset(D)underset(|)CH-underset(CH_(3))underset(|)(CH)CH_(3)+overset(.)BrrarrX+HBr`
Identify the structure of the major products `(X)` from among the following :

A

`CH_(3)-underset(D)underset(|)(CH)-underset(CH_(3))underset(|)(CH)-overset(.)CH_(2)`

B

`CH_(3)-underset(D)underset(|)(CH)-underset(CH_(3))underset(|)overset(.)(C)-CH_(3)`

C

`CH_(3)-underset(D)underset(|)(CH)-CH_(3)`

D

`CH-overset(.)CH-underset(CH_(3))underset(|)(CH)-CH_(3)`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the given problem, we need to analyze the reaction of the compound with bromine radicals and identify the major product formed. Let's break down the steps systematically: ### Step 1: Identify the Structure of the Reactant The reactant is given as: \[ \text{CH}_3\text{CHDCH(CH}_3)\text{CH}_3 \] This structure includes: - A carbon chain with a deuterium (D) atom. - The carbon atoms can be classified as primary and secondary based on their bonding. ### Step 2: Understand the Reaction Mechanism The reaction involves bromine radicals (\( \cdot \text{Br} \)) which will abstract a hydrogen atom from the reactant. This is a free radical substitution reaction. ### Step 3: Determine Possible Hydrogen Abstraction Sites In the reactant, we have: - Primary carbons (two CH3 groups). - Secondary carbons (one CH and one CHD). The bromine radical can abstract hydrogen from either primary or secondary carbons. ### Step 4: Analyze Stability of the Resulting Radicals - **Primary Radical**: Less stable. - **Secondary Radical**: More stable. - **Tertiary Radical**: Most stable (not applicable here). Since the most stable radical will form preferentially, we expect the bromine radical to abstract hydrogen from a secondary carbon (the one attached to deuterium). ### Step 5: Predict the Major Product When the bromine radical abstracts a hydrogen from the secondary carbon (the one with D), we will form a secondary radical. The product will then be: \[ \text{CH}_3\text{CHD}\cdot\text{C(CH}_3)\text{CH}_3 + \text{HBr} \] ### Step 6: Identify the Correct Option Now, let's analyze the options provided: - **Option A**: \( \text{CH}_3\text{CHD}\cdot\text{C(CH}_3)\text{CH}_2 \) - Incorrect, as it suggests a primary radical. - **Option B**: \( \text{CH}_3\text{CHD}\cdot\text{C(CH}_3)\text{CH}_3 \) - Correct, as it represents the stable secondary radical. - **Option C**: \( \text{CH}_3\text{CHD}\text{C(CH}_3)\text{H} \) - Incorrect, as it does not show a radical. - **Option D**: \( \text{CH}\cdot\text{C(CH}_3)\text{CH}_3 \) - Incorrect, as it implies a different structure. ### Conclusion The major product \( X \) formed from the reaction is represented by **Option B**.
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