Home
Class 11
CHEMISTRY
Which of the following is the best way t...

Which of the following is the best way to synthesize `C_(6)_(5)(CH_(2))_(3)CH`?

A

`C_(6)H_(6)+CH_(3)(CH_(2))_(2)CH_(2)Cloverset(AlCl_(3))to`

B

`C_(6)H_(6)+CH_(3)CH_(2)CH_(2)COCloverset(AlCl_(3))tounderset(HCl)overset((Zn)/(Hg))to`

C

`C_(6)H_(6)+(CH_(3)CH_(2)CH_(2)CO)_(2)Ooverset(AlCl_(3))tounderset(OH^(-))overset(H_(2)NNH_(2))to`

D

both (2) and (3)

Text Solution

Verified by Experts

The correct Answer is:
4


In both reaction (2) and (3) the product formed in the first step is `C_(6)H_(5)COCH_(2)CH_(2)CH_(3)`. In both these reactions the electrophile is the acylium ion:
(II) is the main contributing resonance structure for the acylium ion (the electrophile) because both C andO have an octet. Due to resonance, the acylium ion is much more stable than anyl alkyl carbocation thus it cannot rearrange to a more stable cation. In the second step of both the reactions, the ketone obtained i the first step is reduced to the corresponding hydrocarbon.
`C_(6)H_(5)COCH_(2)CH_(2)CH_(3)((Zn)/(Hg), HCl("clemmensen"))/(H_(2)N NH2,OH^(-)("Wolff-kishner"))C_(6)H_(5)(CH_(2))CH_(3)`
Promotional Banner

Topper's Solved these Questions

  • AROMATIC HYDROCARBONS

    R SHARMA|Exercise Follow up Test 7|7 Videos

  • AROMATIC HYDROCARBONS

    R SHARMA|Exercise Question Bank|51 Videos

  • AROMATIC HYDROCARBONS

    R SHARMA|Exercise Follow up Test 5|11 Videos

  • ALKYNES

    R SHARMA|Exercise Archives|42 Videos

  • CHEMICAL BONDING

    R SHARMA|Exercise Archives|73 Videos

Similar Questions

Explore conceptually related problems

Which of the following are benzylic alcohols I C_(6)H_(5)-CH_(2)-CH_(2)OH II C_(6)H_(5)-CH_(2)OH III. C_(6)H_(5)-underset(""CH_(3))underset("| ")"CH"-OH IV. C_(6)H_(5)-CH_(2)-underset(CH_(3))underset("| ")"CH"-OH select the correct option.

Which of the following combinations give C_(6)H_(5)-overset(CH_(3))overset(|)underset(CH_(2)CH_(3))underset(|)C-OH?

Which of the following undergoes haloform reaction? (i) CH_(3)CH_(2)COCH_(2)CI (ii) C_(6)H_(5)COCH_(3) (iii) C_(6)H_(5)COCHI_(2) (iv) CH_(3)CH_(2)COCCI_(3)

C_(6)H_(5)-CH=CH-CO-CH_(3)

Which of the following compounds will show cis-trans isomerism? (i) (CH_(3))_2C=CH-C_(2)H_(5) (ii) CH_(2)=CBr_(2) (iii) C_(6)H_(5)CH=CH-CH_(3) CH_(3)CH="CC"lCH_(3)

The S_(N^(1)) reactivity of the following halides will be in the order: (i) (CH_(3))_(3)C-Br (ii) (C_(6)H_(5))CHBr (iii) (C_(6)H_(5))_(2)C(CH_(3))Br (iv) (CH_(3))_(2)CHBr (v) C_(2)H_(5)Br

Which of the following is the best electron releasing group when present on Benzene ring (A) \(CH_{3}\) (B) \(CH_{3}-CH_{2}\) (C) \(CH_{3})_{2}CH-\) (D) \(CH_{3})_{3}C-\)