Chapter 19: Phenols and Aryl Halides

Practice Problems

19.1

19.2

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19.3

19.4

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19.5

19.6

19.7

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Review Problems

19.8

19.9

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19.10

19.11

19.12

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19.13

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Solution Manual for Solomons, Fryhle and Snyder Organic Chemistry For JEE (Main &
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19.14

19.15

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19.16

19.17

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19.18

19.19

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<H1> ADDITIONAL OBJECTIVE QUESTIONS

<H2> Single Correct Choice Type

1. (b) It is Kolbe Schmitt reaction, CO2 will undergo an electrophilic aromatic

substitution at o position with respect to the stronger activating group OH.

2.(c) P is formed by Friedel Crafts alkylation, involving rearrangement of carbocation from

n-propyl to iso-propyl carbocation. P undergoes the Cumene-Phenol process (or Hock process)
for preparation of Phenol from Cumene (P) alongside formation of acetone.
3. (c) Same solution as 2.
4. (b) The benzene ring in phenol is highly activated toward electrophilic substitution and
hence attempts to directly nitrate it result in charring and copious evolution of oxides of
nitrogen. To reduce the reactivity, the phenol is first sulfonated and thus the nitration is
comparatively smoother. Ipso substitution of -SO3 groups occurs.
5. (a) In basic medium, phenol converts to phenoxide which is a stronger activating group
than amine and thus azo coupling takes place according to the directing influence of OH.
6. (d) Phenol decolorizes bromine water (EAS reaction) while ethanol does not. Ethanol
gives iodoform test (forms yellow ppt.) while phenol does not. The ferric chloride forms a
violet colored complex with the phenol.

7. (c) The compound I is formed by Kolbe Schmitt reaction in which Carboxylic acid
group is introduced at ortho position to OH. The compound II is formed by acylation of
OH group.
8. (a) The SNAr will take place at para position with respect to the strong electron
withdrawing nitro group.
9. (b) The addition of HBr to alkene will take place as per Markovnikov rule.

10. (a) Here, P is , Q is , while R is phenol.

11. (c) Electron withdrawing groups increase reactivity towards SNAr.

12. (a) Dow’s process is used for the manufacture of phenol.

13. (d) Aryl halide reactivity (in SNAr): -F > -Cl > -Br > -I. The more electronegative the group,
the greater is the ability to attract electrons which increases the rate of formation of the
cyclohexadienyl anion.

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14. (d) Electron withdrawing group in the diazonium increase its reactivity towards
azo-coupling.

15. (c) Electron withdrawing group at o/p position increase reactivity towards SNAr. F is
more reactive than Br towards SNAr.
16. (b) In SNAr, electron donating group in the nucleophile and electron withdrawing
group in the Aryl halide increases the rate of reaction.
17. (b) o-nitrophenol has intramolecular H bonding.
18. (d) Electron withdrawing group at o/p position increase reactivity towards SNAr.
19. (d) The bromine water is decolorized and Br is substituted in place of H at all the o
and p positions.
20. (a) In P, nitro group is introduced by nitration, while in the second reaction, the SNAr
will take place at o/p position with respect to the –M nitro group.
21. (b) Azo-coupling will occur at para position with respect to the electron donating OH
group of phenol.

Solution Manual for Solomons, Fryhle and Snyder Organic Chemistry For JEE (Main &
Advanced), Copyright©2017 Wiley India Pvt. Ltd. All rights reserved