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CH(3)-CH=CH(2)overset((i)Hg(OA c)(2)//H(...

`CH_(3)-CH=CH_(2)overset((i)Hg(OA c)_(2)//H_(2)O)underset((ii)NaBH_(4))rarr X+Na rarr Y+CH_(3)Cl rarr Z+HI overset(0^(@)C)rarr A+B`
What are A and B?

A

`CH_(3)-CH_(2)-CH_(2)-OH & CH_(3)O`

B

`CH_(3)-underset(CH_(3))underset("| ")"CH"-OH & CH_(3)I`

C

`CH_(3)-underset(CH_(3))underset("| ")"CH"-OH & CH_(3)OH`

D

`CH_(3)-CH_(2)CH_(2)I & CH_(3)OH`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the question step by step, we will analyze the reactions one by one and identify the products formed at each stage. ### Step 1: Oxymercuration of Propylene The first reaction involves propylene (CH₃-CH=CH₂) reacting with mercuric acetate (Hg(OAc)₂) and water (H₂O). This is an oxymercuration reaction where the double bond is converted into an alcohol. - **Reaction**: \[ CH₃-CH=CH₂ \xrightarrow{Hg(OAc)₂/H₂O} CH₃-CHOH-CH₃ \] - **Product X**: The product formed is isopropyl alcohol (CH₃-CHOH-CH₃), which is a secondary alcohol. ### Step 2: Reduction with Sodium Borohydride Next, we reduce the alcohol using sodium borohydride (NaBH₄). This step replaces the mercury acetate group with a hydrogen atom. - **Reaction**: \[ CH₃-CHOH-CH₃ \xrightarrow{NaBH₄} CH₃-CHOH-CH₃ \] - **Product X remains unchanged**: The product remains isopropyl alcohol (CH₃-CHOH-CH₃). ### Step 3: Reaction with Sodium Now, we react the alcohol (X) with sodium (Na). Sodium reacts with the hydroxyl group to form a sodium alkoxide. - **Reaction**: \[ CH₃-CHOH-CH₃ + Na \rightarrow CH₃-CH(ONa)-CH₃ + \frac{1}{2} H₂ \] - **Product Y**: The product formed is sodium isopropoxide (CH₃-CH(ONa)-CH₃). ### Step 4: Williamson Ether Synthesis Next, we react the sodium alkoxide (Y) with methyl chloride (CH₃Cl) to form an ether through the Williamson synthesis mechanism. - **Reaction**: \[ CH₃-CH(ONa)-CH₃ + CH₃Cl \rightarrow CH₃-CH-CH₃-O-CH₃ + NaCl \] - **Product Z**: The product formed is isopropyl methyl ether (CH₃-CH-CH₃-O-CH₃). ### Step 5: Reaction with Hydroiodic Acid Finally, we react the ether (Z) with hydroiodic acid (HI) at 0°C. At low temperatures, the ether cleaves to form an alcohol and an alkyl halide. - **Reaction**: \[ CH₃-CH-CH₃-O-CH₃ + HI \rightarrow CH₃-CHOH-CH₃ + CH₃I \] - **Products A and B**: The products formed are isopropyl alcohol (A: CH₃-CHOH-CH₃) and methyl iodide (B: CH₃I). ### Final Answer Thus, the final products A and B are: - **A**: Isopropyl alcohol (CH₃-CHOH-CH₃) - **B**: Methyl iodide (CH₃I)

To solve the question step by step, we will analyze the reactions one by one and identify the products formed at each stage. ### Step 1: Oxymercuration of Propylene The first reaction involves propylene (CH₃-CH=CH₂) reacting with mercuric acetate (Hg(OAc)₂) and water (H₂O). This is an oxymercuration reaction where the double bond is converted into an alcohol. - **Reaction**: \[ CH₃-CH=CH₂ \xrightarrow{Hg(OAc)₂/H₂O} CH₃-CHOH-CH₃ ...
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DISHA PUBLICATION-ALCOHOLS, PHENOLS AND ETHERS-Exercise - 2 : Concept Applicator)
  1. Which of the following alcohols on dehydration with conc. H(2)SO(4) wi...

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  2. Dehydration of alcohol by conc. H(2)SO(4) takes place according to fol...

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  3. Product is

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  4. During the dehydration of alcohols to alkenes by heating with conc. H(...

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  5. B(mix)overset(conc.HI)underset(2) larr (CH(3))(3)C-O-CH(3) overset("an...

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  6. ClCH2CH(2)OH is stronger acid than CH(3)CH(2)OH because of :

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  7. CH(3)-CH=CH(2)overset((i)Hg(OA c)(2)//H(2)O)underset((ii)NaBH(4))rarr ...

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  8. What is product of the following sequence of reactions ? (CH(3))(2)C...

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  9. Identify the nature of product in the following reaction

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  10. Which electrophile is likely to be formed as an intermediate in the fo...

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  12. What is the structure of the major product when phenol is treated with...

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  13. The structure of the compound that gives a tribromo derivative on trea...

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  14. "Phenol "overset(NaNO(2)//H(2)SO(4))rarr B overset(H(2)O)rarr C overse...

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  15. The major product P in the following reaction is (CH(3))(3)COH+C(2)H...

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  16. An ether, (A) having molecular formula, C(6)H(14)O, when treated with ...

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  17. HBr reacts with H(2)C=CH-OCH(3) under anhydrous conditions at room tem...

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  18. CH(3)underset(CH(3))underset(|)(CH)-CH=CH(2)underset((ii)H(2)O(2)//OH)...

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  19. The reaction can be classified as:-

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  20. Which one is the most acidic compound?

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