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which of the following reactions of alka...

which of the following reactions of alkanols does not involve c-O bond breadking ?

A

`CH_(3) CH_(2) OH +SOCl_(2)`

B

`CH_(3)CH(OH)CH_(3)+PBr_(3)`

C

`CH_(3)CH_(2)OH+CH_(3)COOH`

D

ROH +HX

Text Solution

AI Generated Solution

The correct Answer is:
To determine which reaction of alkanols does not involve the breaking of the carbon-oxygen (C-O) bond, we will analyze each reaction step by step. ### Step 1: Analyze the First Reaction The first reaction involves CH3CH2OH (ethanol) reacting with SOCl2 (thionyl chloride). - In this reaction, the lone pair of electrons on the oxygen of the alcohol attacks the electrophilic sulfur atom in SOCl2. - This leads to the formation of an intermediate where the C-O bond is broken as the hydroxyl group (OH) is replaced by a chlorine atom (Cl). - Therefore, this reaction **involves C-O bond breaking**. **Hint:** Look for the replacement of the hydroxyl group in reactions involving thionyl chloride. ### Step 2: Analyze the Second Reaction The second reaction involves CH3CH(OH)CH3 (isopropanol) reacting with PBr3 (phosphorus tribromide). - Here, the hydroxyl group (OH) is replaced by a bromine atom (Br). - This also results in the breaking of the C-O bond as the OH group is substituted. - Thus, this reaction **also involves C-O bond breaking**. **Hint:** Substitution reactions typically involve breaking the C-O bond when replacing the hydroxyl group. ### Step 3: Analyze the Third Reaction (Esterification) The third reaction is an esterification reaction where a carboxylic acid (CH3C(=O)OH) reacts with an alcohol (CH3CH2OH) in the presence of concentrated H2SO4. - In this reaction, the concentrated H2SO4 acts as a dehydrating agent. - The bond between the oxygen and hydrogen (O-H) of the alcohol is broken to form water, but the C-O bond remains intact. - Therefore, this reaction **does not involve C-O bond breaking**. **Hint:** Look for reactions that form water as a byproduct; they may not involve C-O bond breaking. ### Step 4: Analyze the Fourth Reaction The fourth reaction involves an alcohol reacting with an acid (HX). - In this case, the alcohol donates its lone pair to the proton (H+) from the acid, forming an oxonium ion (R-OH2+). - To stabilize the positive charge, the C-O bond is broken, leading to the formation of a carbocation and the release of water. - Hence, this reaction **involves C-O bond breaking**. **Hint:** Protonation of alcohols typically leads to C-O bond cleavage. ### Conclusion After analyzing all four reactions, we find that the only reaction that does not involve the breaking of the C-O bond is the **third reaction (esterification)**. ### Final Answer The reaction of esterification does not involve C-O bond breaking.
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VMC MODULES ENGLISH-ALCOHOLS, PHENOLS & ETHERS-Efficient
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