Question

1. Which of the following reagent(s) can be used to prepare a mixture of o and p-nitro toluene from toluene

(A) HNO₂ (B) HNO₃ (C) HNO₃/Fe (D) HNO₃/H₂SO₄ (E) NaNO₂

2.

(A) H₂SO₃ (B) SO₃/ Which of the following reagent(s) can be used to convert nitrobenzene to m-nitrobenzenesulfonic acid Fe (C) H₂SO₃/Fe (D) H₂SO₄/Al₂(SO₄)₃ (E) H₂SO₄.SO₃

3. Which of the following reagent(s) can be used to prepare bromobenzene from benzene

(A) NBS (B) Br₂/FeBr₃ (C) H₂SO₄/Br₂ (D) Br₂/AlBr₃ (E) Br₂/Pd

4. Which of the following functional groups are o,p-directing ?

(A) Br, CH₂CH₃, NH₂ (B) Cl, NH₂, COOH (C) I, SO₃H, OH (D) OCH₃, Cl, COCH₃ (E) NO₂, CH₃, OH

5. Which of the following reagent(s) gives the reaction below

(A) CH₃Cl (B) Cl₂/ Fe (C) Cl₂/ AlCl₃ (D) Cl₂/ FeCl₃ (E) Cl₂/ HCl

6. Friedal-Craft acylation reagent(s)

(A) CH₃Cl/AlCl₃ (B) Cl₂/CH₃COCl (C) CH₃COCl/AlCl₃ (D) CH₃COCl/FeCl₃ (E) CH₃Cl/FeCl₃

7. Which of the following functional groups are m-directing ?

(A) NO₂, CH₃, OH (B) Br, NH₂, COOH (C) I, SO₃H, OH (D) OCH₃, Cl, COCH₃ (E) COCH_3, SO₃H, CHO

8. Which of the following compound can be used in the Diels-Alder reaction

(A) 2-methyl, 2,4-hexadiene (B) 2,5-hexadiene (C) 1-methyl,cyclohexa-1,4-diene (D) cyclohexa-1,4-diene

(E) 2-methyl, 1,5-hexadiene

9. Which statement about benzene is incorrect?

(A) The C�C p - bonding is delocalized (B) The C₆ ring is planar (C) The average C - C bond distance is the same as C-C double bonds (D) Each C atom is sp² hybridized ( E ) There are 12 s (sigma) bonds in benzene

10. Which of the following is NOT aromatic

(A) Cyclopropenyl cation (C₃H₃⁺) (B) Benzene (C₆H₆) (C) [16]-Annulene (C₁₆H₁₆)

(D) Cycloheptatrienyl cation (C₇H₇⁺) (E) [18]-Annulene (C₁₈H₁₈)

11. Conjugate addition of one equivalent of deuterium bromide (DBr) to 1,3-butadiene gives

(A) 3-bromo, 4-deutero, 1-butene (B) 3-bromo, 4-deutero, 2-butene (C) 4-bromo, 3-deutero, 1-butene (D) 1-bromo, 4-deutero, 2-butene (E) 1-bromo, 4-deutero, 1-butene

12. Which of the following is a conjugated diene

(A) cyclopentadiene (B) 2-methylcyclohexanone (C) 1-methyl,cyclohexa-1,4-diene (D) cyclohexa-1,4-diene

(E) cycloocta-1,5-diene

13. The aromatic compound is

14. Which of the following reaction involves a benzyne mechanism ?

(A) Ph-CH₃ ? Ph-COOH (B) Ph-CH₃ ? Ph-CHO (C) Ph-OH ? Ph-Cl (D) Ph-Cl ? Ph-OH

(E) none of these

15. Which of the following reagent(s) can be used to prepare a mixture of o and p-nitro toluene from

toluene

(A) HNO₂ (B) HNO₃ (C) HNO₃/Fe (D) HNO₃/H₂SO₄ (E) NaNO₂

16. Friedal-Craft alkyation reagent(s)

(A) C₂H₅Cl/AlCl₃ (B) Cl₂/CH₃COCl (C) CH₃COCl/AlCl₃ (D) CH₃COCl/FeCl₃ (E) CH₃Cl/FeCl₃

17. Which of the following functional groups are o,p-directing ?

(A) NO₂, SO₃H, CHO (B) Br, NH₂, COOH (C) I, OH, CH₃ (D) OCH₃, Cl, COCH₃ (E) COCH_3, SO₃H, Br

18. Major product in the reaction of benzene with 1-bromopropane, in the presence of AlBr₃ catalyst

(A) bromobenzene (B) n-propylbenzene (C) iso-propylbenzene (D) o-bromo-n-propylbenzene

(E) p-bromo-n-propylbenzene

19. Which of the following is the electrophile in the nitration reaction

(A) ⁺HNO₂ (B) NO₂⁺ (C) N₂+ (D) HNO₃/H₂SO₄ (E) NO₃⁺

20. Which of the following is the electrophile in the sulfonation reaction

(A) ⁺HSO₂ (B) SO₂⁺ (C) SO₃⁺ (D) SO₃/H₂SO₄ (E) HSO₃⁺

21. Which of the following is the electrophile in the Friedel-Craft acylation reaction

(A) RCO₂⁺ (B) RCO⁺ (C) CO₂⁺ (D) RX/H₂SO₄ (E) RCO₃⁺

22. The benzyne intermediate has �� p bonds

(A) 1 (B) 2 (C) 3 (D) 4 (E) 5

23. The reagent used for Allylic/benzylic bromination is:

(A) NBS (B) Br₂/ Fe (C) Br₂/ AlBr₃ (D) Br₂/ FeBr₃ (E) Br₂/ HBr

24. Which of the following is an oxidation reagent

(A) H₂SO₄ (B) KMnO₄ (C) KMnO₂ (D) NaBH₄ (E) AlCl₃

25. The formula of fuming sulfuric acid

(A) H₂SO_4.SO₃ (B) H₂SO_4.SO₂ (C) H₂SO_4.HSO₂ (D) H₂SO_4.HSO₃ (E) H₂SO_4.SO

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26. How do you prepare the following compounds, starting from benzene ?

(a). aniline (b). Iodo benzene (c). benzoic acid (d). benzylbromide (e). m-methyl benzoic acid

(f). p-nitrobenzoic acid (g) m-nitrobenzoic acid (h). p-chlorobenzenesulfonic acid (i). m-chlorobenzenesulfonic

acid (j) 3-isopropyl benzoic acid (k). 4-isopropyl toluene

27. Draw the product(s) from the following reactions showing the mechanisms

(a) 1,3-butadiene with acrylonitrile

(b) 1,3-butadiene with one eqv. HBr

(c) 1,3-cyclohexadiene with acrylonitrile

(d) 1,3-cyclohexadiene with one eqv. HBr

(e) 1,3-cyclohexadiene with two eqv. HBr

(f) cyclopentadiene with two eqv. HBr

28. How do you prepare the following compounds, starting from toluene ?

(a). benzoic acid (b). benzyl alcohol (c). m-bromobenzoic acid (d). m-methylbenzoic acid (e). m-nitro

benzoic acid (f). p-nitrobenzoic acid

29. What is/are the product(s) expected when ethylbenzene is reacted with

(a). NBS

(b). Br₂/FeBr₃

(c). KMnO₄, then H⁺

(d). fuming H₂SO₄

(e). NBS, then aq. NaOH

(f) iso-butylbromide/AlBr₃