Organic Chemistry Test Bank Chapter 4 (Part B)

Organic Chemistry Test Bank – Chapter 4 (Part B)

In every slide, you will find a question with 2 – 5 choices.

The answers of the questions will be in the last slide, so don’t forget to write your answers (To check them 💪).

*** You can use the periodic table anytime 😊.

1. Electrophilic substitution on phenol occurs primarily at which position(s)?

A. Ortho.

B. Meta.

C. Para.

D. Ortho & para.

E. Meta & para.

2. What will be the product formed when phenol reacts with Br2 in FeBr3

medium?

A. 3-Bromophenol.

B. 4- Bromophenol.

C. 3,5-Dibromophenol.

D. 2,4,6-Tribromophenol.

3. What will be the product in the given reaction?

A. m-chlorophenol.

B. o-chlorophenol and p-chlorophenol.

C. o-hydroxytoluene and p-hydroxytoluene.

D. m-hydroxytoluene.

4. What is the electrophile in the acylation of benzene?

A. AlCl3.

B. CO+.

C. Cl+.

D. R-CO+.

5. How would you synthesis the following reaction?

A. conc. HNO3 + conc. H2SO4.

B. conc. HNO3.

C. AlCl3 + Ph-NO2.

D. conc. H2SO4 + Oleum.

6. Which of the following is the most activating in electrophilic aromatic substitution?

A. -NO2.

B. -NHCOCH3.

C. -CN.

D. -NH2.

7. When considering electrophilic aromatic substitution reactions electron withdrawing substituents (e.g. nitro) are described as:

A. Ortho/para directing and activating.

B. Ortho/para directing and deactivating.

C. Meta directing and activating.

D. Meta directing and deactivating.

8. When considering electrophilic aromatic substitution reactions, the halides are described as:

A. Ortho/para directing and activating.

B. Ortho/para directing and deactivating.

C. Meta directing and activating.

D. Meta directing and deactivating.

9. When considering electrophilic aromatic substitution reactions electron donating substituents (e.g. methoxy) are described as:

A. Ortho/para directing and activating.

B. Ortho/para directing and deactivating.

C. Meta directing and activating.

D. Meta directing and deactivating.

10. Among the following, which one is not a meta directing group in an electrophilic attack?

A. A.

B. B

C. C.

D. D.

A B

C D

11. Nitro group is meta-directing in electrophilic aromatic substitution reactions?

A. Increases electron density at meta-position.

B. Increases electrons density at ortho and para-positions.

C. Decreases electron density at meta-position.

D. Decreases electron density at ortho and para-positions.

12. Which of the following substituents is not an ortho–para director?

A. -Br.

B. -I.

C. -Cl.

D. -F.

E. -CN.

13. What compounds are formed when bromobenzene is chlorinated?

A. Ortho-bromochlorobenzene.

B. Meta-bromochlorobenzene.

C. Para-bromochlorobenzene.

D. A and C.

E. A, B, and C.

14. How many resonance contributors are there for the carbocation intermediates formed when phenol undergoes ES in the o, m, p positions?

A. o: 3 m: 3 p: 3.

B. o: 4 m: 3 p: 4.

C. o: 3 m: 3 p: 4.

D. o: 4 m: 3 p: 3.

E. o: 3 m: 4 p: 3.

***Note: ES stands for Electrophilic Aromatic Substitution. Also, (o, m, p) stands for (ortho, meta, para).

15. Which of the following is an ortho–para director?

A. -OH.

B. -SO3H.

C. -Br.

D. A and C.

E. A, B, and C.

16. How many contributing resonance structures are there for the intermediate formed when protonated aniline undergoes ES in the o, m, p positions?

A. o: 3 m: 3 p: 3.

B. o: 4 m: 3 p: 4.

C. o: 3 m: 4 p: 3.

D. o: 3 m: 3 p: 4.

E. o: 4 m: 3 p: 3.

***Note: ES stands for Electrophilic Aromatic Substitution. Also, (o, m, p) stands for (ortho, meta, para).

17. What is the name of the following compound?

A. A.

B. B.

C. C.

D. D.

Choice I II

A HNO3 H2SO4

B HNO3 / H2SO4 Br2 / FeBr3

C Br2 FeBr3

D Br2 / FeBr3 HNO3 / H2SO4

Benzene m-Bromonitrobenzene

18. What is the name of the following compound?

A. A.

B. B.

C. C.

D. D.

Choice I II

A HNO3 H2SO4

B HNO3 / H2SO4 Br2 / FeBr3

C Br2 FeBr3

D Br2 / FeBr3 HNO3 / H2SO4

Benzene p-Bromonitrobenzene

19. Which of the following molecules is the most reactive toward electrophilic aromatic substitution?

A. A.

B. B.

C. C.

D. Can’t be determined.

A B C

20. Which is the best reaction sequence to synthesize m-bromobenzenesulfonic acid from benzene?

A. 1) Br2, AlBr3, 2) H2SO4, SO3.

B. 1) H2SO4, SO3 2) Br2, AlBr3.

C. 1) ethene, HF, 2) Br2, AlBr3.

D. 1) CH3Cl, AlCl3, 2) Br2, AlBr3.

E. 1) Br2, AlBr3, 2) CH3COCl, AlCl3.

21. Match the substituent to the stated orientation and activation effects. Which set is incorrect?

A. Cl; activating; o- and p-directing.

B. NO2; deactivating; m-directing.

C. OH; activating; o- and p-directing.

D. Methyl; activating; o- and p-directing.

22. An NH2 substituent in an aromatic ring is:

A. Deactivating, and meta-directing.

B. Activating, and meta-directing.

C. Activating, and ortho- and para-directing.

D. Deactivating, and ortho- and para-directing.

23. Would you expect the aromatic ring in the following compound to be:

A. Deactivated by induction and resonance.

B. Deactivated by induction but activated by

resonance.

C. Activated by induction but deactivated by

resonance.

D. Activated by induction and resonance.

E. Not activated at all.

24. See the trend in the following (Substituent to react with HNO3), the correct statement is:

A. As we go down, the percentage of ortho

structures increases and become major.

B. As we go down, the percentage of meta

structures increases and become major.

C. As we go down, the percentage of para

structures increases and become major.

D. Can’t be determined.

(1): -CH3.

(2): -CH2CH3.

(3): -CH(CH3)2.

(4): -C(CH3)3.

25. See the trend in the following (Substituent to react with HNO3), the correct statement is:

A. As we go down, the steric effect increases.

B. As we go down, the steric effect decreases.

C. As we go down, the steric effect stays the

same.

D. Can’t be determined.

(1): -CH3.

(2): -CH2CH3.

(3): -CH(CH3)2.

(4): -C(CH3)3.

The key answers

Question No. Answers Question No. Answers Question No. Answers

1. D 10. C 19. A

2. B 11. D 20. B

3. C 12. E 21. A

4. D 13. D 22. C

5. A 14. B 23. D

6. D 15. D 24. C

7. D 16. A 25. A

8. B 17. B Note: This part contains lessquestions because a lot of thematerials related to arenes are notrequired for the exam.9. A 18. D