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Quiz 3-Practice questions (1) نسخة

This document contains a 16 question practice quiz on aromatic compounds, alcohols, phenols, and thiols from chapters 4, 7, and 8. The quiz covers topics like the properties of benzene, electrophilic aromatic substitution reactions, naming substituted aromatic compounds, reaction mechanisms, and properties of alcohols and phenols. It also includes two longer form questions asking to outline synthesis routes and draw a reaction mechanism.

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Sabaa Abuzaid
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341 views

Quiz 3-Practice questions (1) نسخة

This document contains a 16 question practice quiz on aromatic compounds, alcohols, phenols, and thiols from chapters 4, 7, and 8. The quiz covers topics like the properties of benzene, electrophilic aromatic substitution reactions, naming substituted aromatic compounds, reaction mechanisms, and properties of alcohols and phenols. It also includes two longer form questions asking to outline synthesis routes and draw a reaction mechanism.

Uploaded by

Sabaa Abuzaid
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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Name: _______________________________________CHEM 226 Practice Quiz 3

Chapter 4-Aromatic Compounds and


Chapter 7- Alcohols, Phenols and Thiols
Attempt all questions showing your answers and work clearly for full and partial
credits
1. Which of the following statements about benzene is FALSE?
A) the molecule is planar and each carbon is at a corner of regular hexagon
B) there are two resonance structures of equivalent energy
C) the bond angles are all 120º and the bond lengths are all 1.39Å
D) the typical mechanism by which reactions occur is by addition
E) each carbon in the benzene ring is sp2 hybridized

2. Which of the following is NOT an electrophile in an electrophilic aromatic substitution


reaction?
A) NO2+
B) (CH3)3C+
C) SO3
D) Cl-
E) all are
3. What is the correct name for the following molecule?

A) o-bromobenzyl
B) biphenyl bromide
C) 2-bromodiphenylpropane
D) bromobenzylbenzene
E) o-benzylbromobenzene

4. Which of the following groups is a meta director?


A) –Cl
B) –COOH
C) –OCH3
D) –OH
E) –NH2
5. What is the name of the major product from the following sequence of reactions?

A) aniline D) phenol
B) anisole E) toluene
C) benzoic acid

  1  
6. Which is the best reaction sequence to synthesize m-bromobenzenesulfonic acid from
benzene?

A) 1) Br2, FeBr3, 2) H2SO4, SO3


B) 1) H2SO4, SO3 2) Br2, FeBr3
C) 1) ethene, HF, 2) Br2, FeBr3
D) 1) CH3Cl, AlCl3, 2) Br2, AlBr3
E) 1) Br2, FeBr3, 2) CH3COCl, AlCl3

7. In the mechanism for the nitration of benzene, what is the function of H2SO4?
A) to act solely as a solvent
B) to donate a proton to HNO3
C) to accept a proton from HNO3
D) to generate heat for reaction to occur
E) to protonate the benzene ring

8. Among the following groups, which ones are o,p-directing?

A) 1, 3, and 5
B) 1 and 5
C) 2 and 4
D) 2, 3, and 4
E) 1 and 3

9. The relative rates of nitration of the following are:

A) 1 > 2 > 3 > 4 D) 3 > 4 > 2 > 1


B) 4 > 2 > 1 > 3 E) 3 > 2 > 1 > 4
C) 2 > 1 > 4 > 3

  2  
10. What is the best sequence of reactions to synthesize m-nitrophenol?
A) D)

B) E)

C)

11. Which group is both ortho-para directing and ring deactivating?


A) –Cl
B) –CH3
C) –NO2
D) –CHO
E) –OCH3

12. The only group among the following that is m-directing is:

A)

B)

C)

D)

E)

13. The name of the following molecule is:

A) toluene D) styrene
B) ethylbenzene E) anisole
C) cumene

  3  
14. What is the product of the following reaction?

A) D)

B) E)

C)

15. Which position would be para to X?

A) 1
B) 2
C) 3
D) 4
E) 6

  4  
16. Starting with benzene as the only aromatic organic starting material, outline a plausible
synthesis route for each of the listed compounds showing all reagents, conditions and
intermediate substitution products clearly. The conversions are possible in at most 3
steps and at least 2 steps. (In case of a repeating step, use excess reagents and show as
one step)
20 pts

  5  
17. Using chlorination of benzene as an example, write the reaction mechanism for
showing all possible resonance structures of intermediates if any for the
electrophilic aromatic substitution of benzene. 10pts

Chapter 8 Questions

1. Which of the following is a secondary (2°) alcohol?

A) I
B) II
C) III
D) IV
E) V

2. What is the IUPAC name for isobutyl alcohol?


A) 1-butanol
B) 2-butanol
C) 2-methyl-2-butanol
D) 2-methyl-1-propanol

– +
3. What is a correct name for (CH3)3CO Na ??
A) sodium alkoxide
B) sodium trimethyloxide
C) sodium butoxide
D) sodium trimethylethoxide
E) sodium tert-butoxide

  6  
4. The correct name for is

A) 2-hydroxybromobenzene.
B) 2-bromobenzyl alcohol.
C) 2-bromobenzol.
D) o-bromophenol.
E) 2-bromohexanol

5. If the pKa of isopropyl alcohol is 17, what is the Ka of isopropyl alcohol?


A) 17 ´ 10–17
B) 10–17
C) 10–3
D) 1017
E) 103
F) 17 ´ 1017

6. Which of the following phenols is the strongest acid?


A) D)

B) E)

C)

7. Phenols are stronger acids than alcohols because of the


A) resonance stabilization of phenoxide ions.
B) resonance stabilization of phenols.
C) resonance stabilization of alkoxide ions.
D) resonance stabilization of alcohols.
E) hydrogen bonding in phenols.

8. Which reagents would you use to accomplish the following transformation?

  7  
A)H2SO4, H2O, acetone
B)CrO3, H2SO4, acetone
C)PCC/CH2Cl2
D)Zn, HCl, acetone
E)H2, Pd, acetone
9. What reagents would accomplish the following transformation?

A) 1. PCl3 2. H3O+
B) CrO , H in acetone
3
C) PCC, CH2Cl2
D) 1. Na 2. CH3OH
E) none of the above

  8  

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