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The major product (Y) in the following reactions is: CH3–CH(CH3)–C≡CH (i) HgSO4, H2SO4 (ii) C2H5MgBr, H2O (iii) Conc. H2SO4/Δ

1. CH3–C(CH3)=C(CH3)–C2H5
2. H3C–C(=CH2)–CH(C2H5)–CH3
3. CH3–CH(CH3)–C(C2H5)=CH2
4. CH3–CH(CH3)–C(CH3)=CH–CH3

Correct answer: CH3–C(CH3)=C(CH3)–C2H5

Solution

HgSO4/H2SO4 gives the methyl ketone (CH3)2CH-CO-CH3; C2H5MgBr/H2O gives the tertiary alcohol (CH3)2CH-C(OH)(CH3)-C2H5; conc. H2SO4 dehydrates by Zaitsev toward the isopropyl CH to give the tetrasubstituted alkene CH3-C(CH3)=C(CH3)-C2H5.

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