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In the following reaction sequence Ph ...

In the following reaction sequence
`Ph -C -= CH underset(Hg^(2+)) overset(aq.H_(2)SO_(4)) rarr A underset(2.H_(2)O)overset(1.CH_(3)MgI)rarr B`
the product `(B)` is

A

`PhCOCH_(3)`

B

`PhCH_(2)CHOHCH_(3)`

C

D

`PhCH_(2)COCH_(3)`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the given reaction sequence, we will break down each step in detail. ### Step 1: Reaction of Phenylacetylene with Hg²⁺ and H₂SO₄ The starting compound is phenylacetylene (Ph-C≡C-H). When phenylacetylene reacts with mercuric ion (Hg²⁺) in the presence of aqueous sulfuric acid (H₂SO₄), it undergoes a hydration reaction. 1. **Formation of a Mercurinium Ion**: - The triple bond (C≡C) reacts with Hg²⁺, forming a mercurinium ion. This ion is a cyclic structure where the mercury atom is bonded to one of the carbons of the triple bond. - The structure can be represented as: ``` Ph-C(Hg)-C ``` 2. **Nucleophilic Attack by Water**: - Water (H₂O) acts as a nucleophile and attacks the more substituted carbon atom of the mercurinium ion, leading to the formation of an intermediate. - This gives us a compound with a hydroxyl group (OH) and a hydrogen atom on the other carbon: ``` Ph-C(OH)-C(Hg)-H ``` 3. **Deprotonation**: - The intermediate loses a proton (H⁺), leading to the formation of an enol: ``` Ph-C(=C)-OH ``` 4. **Tautomerization**: - The enol tautomerizes to form a ketone (A). The double bond shifts, and we end up with: ``` Ph-C(=O)-CH₃ ``` - This compound is a phenyl ketone (acetophenone). ### Step 2: Reaction of Compound A with CH₃MgI Now, we take the product A (acetophenone) and react it with methylmagnesium iodide (CH₃MgI). 1. **Nucleophilic Addition**: - The Grignard reagent (CH₃MgI) acts as a nucleophile and attacks the carbonyl carbon of the ketone (A). - This results in the formation of a tetrahedral intermediate: ``` Ph-C(OH)(CH₃)-CH₃ ``` 2. **Protonation**: - The intermediate is then protonated by water (H₂O) to yield the final product (B): ``` Ph-C(OH)(CH₃)-CH₃ ``` - This compound is a tertiary alcohol. ### Final Product The final product B is a tertiary alcohol, specifically 1-phenyl-2-propanol. ### Summary of the Reaction Sequence 1. **Starting Material**: Ph-C≡C-H (Phenylacetylene) 2. **Intermediate A**: Ph-C(=O)-CH₃ (Acetophenone) 3. **Final Product B**: Ph-C(OH)(CH₃)-CH₃ (1-phenyl-2-propanol) ### Answer The product B is **1-phenyl-2-propanol**. ---
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ALLEN-ALKENE, ALKANE & ALKYNE -EXERCISE-1
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  2. Consider the following chlorides: The order of reactivity of A, B...

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  3. In the following reaction sequence Ph -C -= CH underset(Hg^(2+)) ove...

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  4. Consider the following reaction. CH(3)overset(O^(16))overset(||)C-O^...

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  5. Consider the following reaction sequence, underset(2 H(2)O)overset ...

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  6. Propene is allowed to react with m-chloroperoxybenzoic acid. The produ...

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  7. 2-Phenylethanol may be prepared by the reaction of phenyl magnesium br...

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  8. In the reaction the product (B) is:

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  9. The final product in the reaction is : Ph-OH+C Cl(4)overset(KOH)rarr...

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  10. When phenol is treated with CHCl(3) and NaOH, the product formed is

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  11. about above reaction the incorrect statement is

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  12. Final product D in the sequence of reaction is

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  13. The reaction of 1 mol each of p-hydroxyacetophenone and methyl magnesi...

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  14. The product obtained in the reaction underset(OH)underset(|)RCH-CH(2)o...

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  15. The final product obtained in the reaction is :

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  16. The acidity of the compounds RCOOH, H(2)CO(3),C(6)H(5)OH, ROH decrease...

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  17. Arrange the following in order of decreasing acidic strength. p-nitrop...

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  18. Order of reactivity of hydrogen halides towards ethers is

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  19. Consider the following reactions : The product (B) is

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  20. The major product (A) formed in the reaction- overset(H(2)SO(4))rar...

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