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Organic Chemistry II - Midterm Exam 1 - Fall 2010 | CHM 2211, Exams of Organic Chemistry

Material Type: Exam; Professor: Ye; Class: Organic Chemistry II; Subject: Chemistry; University: University of Central Florida; Term: Summer Session 2010;

Typology: Exams

2009/2010

Uploaded on 11/17/2010

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CHM2211-0001 Fall 2010 Instructor: Dr. Jingdong Ye
Midterm exam I
September 17, 2010
Total number of questions: 25 Total points: 25 Exam duration: 50 min
Note: choose only one correct and best answer for each question!
Tip: work on the easy and fast questions first, come back for harder ones.
1. The IUPAC name of the following compound is:
a. 2,3,5-Trimethyltoluene
b. 1,2,3,5-Tetramethylbenzene
c. 2,4,6-Trimethyltoluene
d. 2,3,5-Trimethyl-1-toluene
e. 1,2,4,6-Tetramethylbenzene
2. The IUPAC name of the following compound is:
a. 2-Phenyl-5-methylhexane
b. (1,4-Dimethylpentyl)benzene
c. 1,4-Dimethylpentylbenzene
d. 2,5-Dimethylpentylbenzene
e. 2-Methyl-5-phenylhexane
3. How many aromatic rings are there in the following compounds?
N
N
N
N
NH
2
O
OHOH
HO
N
N NH
2
N
+
S
OH
(i) (ii)
a. (i) 1; (ii) 1
b. (i) 1; (ii) 2
c. (i) 1; (ii) 3
d. (i) 2; (ii) 2
e. (i) 2; (ii) 3
4. How many electrons in total do the nitrogen atoms contribute to the aromatic systems in the
compounds in Question 3?
a. (i) 3; (ii) 3
b. (i) 3; (ii) 4
1
Name:
PID:
pf3
pf4
pf5

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CHM2211-0001 Fall 2010 Instructor: Dr. Jingdong Ye

Midterm exam I

September 17, 2010 Total number of questions: 25 Total points: 25 Exam duration: 50 min Note: choose only one correct and best answer for each question! Tip: work on the easy and fast questions first, come back for harder ones.

  1. The IUPAC name of the following compound is: a. 2,3,5-Trimethyltoluene b. 1,2,3,5-Tetramethylbenzene c. 2,4,6-Trimethyltoluene d. 2,3,5-Trimethyl-1-toluene e. 1,2,4,6-Tetramethylbenzene
  2. The IUPAC name of the following compound is: a. 2-Phenyl-5-methylhexane b. (1,4-Dimethylpentyl)benzene c. 1,4-Dimethylpentylbenzene d. 2,5-Dimethylpentylbenzene e. 2-Methyl-5-phenylhexane
  3. How many aromatic rings are there in the following compounds? N N N N NH 2 O OH OH HO N N NH 2 N+ S OH (i) (ii) a. (i) 1; (ii) 1 b. (i) 1; (ii) 2 c. (i) 1; (ii) 3 d. (i) 2; (ii) 2 e. (i) 2; (ii) 3
  4. How many electrons in total do the nitrogen atoms contribute to the aromatic  systems in the compounds in Question 3? a. (i) 3; (ii) 3 b. (i) 3; (ii) 4 Name: PID:

c. (i) 3; (ii) 5 d. (i) 4; (ii) 6 e. none of the above

  1. Which of the following compound is the most stable one? O O O (a) (b)^ (c)
  2. Which of the following alkyl halides would you expect to undergo Friedel-Crafts reaction without rearrangement? (a) CH 3 CH 2 CH(Cl)CH 3 (b) CH 3 CH 2 CH 2 Cl (c) (CH 3 ) 3 CCH 2 Cl (d) (CH 3 ) 2 CHCH 2 Cl (e) (CH 3 ) 2 CCH 2 Cl Ph
  3. Considering the substituent effect of nitroso group (-N=O) on electrophilic aromatic substitution, which of the following statement is true? a. it’s a meta-directing deactivator b. it’s an ortho- and para-directing activator c. it has an activating inductive effect d. it has an activating resonance effect e. none of the above
  4. About Friedel-Crafts reaction, which of the following statement is true? a. Aniline undergo fast Friedel-Crafts alkylation because of the activating effect of amino group b. Benzoic acid can’t undergo Friedel-Crafts alkylation c. When Benzene react with acetyl chloride (CH 3 COCl), it’s hard to stop after the first substitution d. Both -NHCOCH 3 and -NO 2 substituents are deactivating and inhibit Friedel-Crafts acylation e. All of the above
  5. At which numbered position would you expect the following compound to undergo electrophilic aromatic bromination (Br 2 /FeBr 3 )? a. 1 b. 2 c. 3 d. 4
  6. At which numbered position would you expect the compound in Question 9 to undergo Friedel-Crafts acylation? a. 1 b. 2 c. 3 d. 4 NH 2 1 2 3 4

a. 1. Cl 2 , FeCl 3 ; 2. HNO 3 , H 2 SO 4 ; 3. CH 3 Cl, AlCl 3 ; 4. KMnO 4 , H 3 O+ b. 1. HNO 3 , H 2 SO 4 ; 2. Cl 2 , FeCl 3 ; 3. CH 3 Cl, AlCl 3 ; 4. KMnO 4 , H 3 O+ c. 1. HNO 3 , H 2 SO 4 ; 2. CH 3 Cl, AlCl 3 ; 3. Cl 2 , FeCl 3 ; 4. KMnO 4 , H 3 O+ d. 1. CH 3 Cl, AlCl 3 ; 2. HNO 3 , H 2 SO 4 ; 3. Cl 2 , FeCl 3 ; 4. KMnO 4 , H 3 O+

  1. To synthesize the following molecule from benzene, the best route is? Br a. 1. CH 3 CH 2 CH 2 Cl, AlCl 3 ; 2. Br 2 , FeBr 3 ; 3. NBS, (PhCO 2 ) 2 ; 4. KOH, ethanol b. 1. CH 3 CH 2 COCl, AlCl 3 ; 2. H 2 , Pd/C; 3. Br 2 , FeBr 3 ; 4. NBS, (PhCO 2 ) 2 ; 5. KOH, ethanol c. 1. 1-Chloropropene, AlCl 3 ; 2. Br 2 , AlCl 3 d. 1. 1-Chloropropene, AlCl 3 ; 2. Br 2 , FeBr 3 e. 1. 1-Chloropropene, FeCl 3 ; 2. Br 2 , AlBr 3
  2. The IUPAC name of the following compound is: a. 4-Bromo-2-cyanophenol b. o -Cyano- p -bromophenol c. p -Bromo- o -cyanophenol d. 3-cyano-4-hydroxylbromobenzene e. m -cyano- p -hydroxylbromobenzene
  3. Rank the following substances in order of increasing acidity. (1) (2) (3) (4) (CH 3 ) 2 CHOH HCCH (CF 3 ) 2 CHOH CH 3 OH a. (1)<(2)<(3)<(4) b. (2)<(1)<(3)<(4) c. (2)<(1)<(4)<(3) d. (3)<(4)<(1)<(2) e. none of the above
  4. The best route to carry out the following transformation is? CO 2 H (^) CH 2 SH a. 1. H 2 , Pd/C; 2. NaSH b. 1. (i) NaBH 4 , (ii) H 3 O+; 2. PBr 3 ; 3. NaSH c. 1. (i) LiAlH 4 , (ii) H 3 O+; 2. PBr 3 ; 3. NaSH d. 1. NaSH; 2. H 2 , Pd/C e. 1. NBS, (PhCO 2 ) 2 ; 2. (i) NaBH 4 , (ii) H 3 O+; 3. PBr 3 ; 4. NaSH
  5. What are the missing reagents for the following three reactions? Br OH CN

CH 3 CCH 2 CH 2 COCH 3 O O CH 3 CHCH 2 CH 2 COCH 3 OH O CH 3 CCH 2 CH 2 COCH 3 O O CH 3 CHCH 2 CH 2 CH 2 OH OH

O OH

  1. (i)

  2. H 3 O+

  3. (ii)

  4. H 3 O+

  5. (iii)

  6. H 3 O+ a. (i) LiAlH 4 , (ii) LiAlH 4 , (iii) LiAlH 4 b. (i) NaBH 4 , (ii) NaBH 4 , (iii) NaBH 4 c. (i) LiAlH 4 , (ii) NaBH 4 , (iii) NaBH 4 d. (i) NaBH 4 , (ii) NaBH 4 , (iii) LiAlH 4 e. (i) NaBH 4 , (ii) LiAlH 4 , (iii) LiAlH 4

  7. Which of the following transformation is correct? C O CH 3 + BrMgCH 3 C O OCH 3 +^2 BrMgCH 3 C O CH 3 CH 3 + BrMg C OH CH 3 CH 3 a. b. c. d. All of the above.

  8. The follow dehydration can be done with? OH a. H 3 O+, 50 oC b. HBr c. POCl 3 , pyridine d. both a and b e. both a and c

  9. The best route for the following transformation is?

Key: 1.b 2.e 3.d 4.c 5.a 6.a 7.d 8.b 9.d 10.b 11.a 12.e 13.c 14.d 15.d 16.b 17.a 18.c 19.c 20.e 21.d 22.e 23.d 24.c 25.a