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Exam 3 with Answer Key - Organic Chemistry I | CHM 2210, Exams of Chemistry

Material Type: Exam; Professor: Herriott; Class: Organc Chem I; Subject: Chemistry; University: Florida International University; Term: Fall 2007;

Typology: Exams

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CHM 2210: ORGANIC CHEMISTRY II Third Exam, Form 3
Section 02, Professor A. Herriott November 29, 2007
No electronic devices (calculators, cell phones, laptops, etc) may be used or consulted during the exam.
All scrap work should be done on the extra page provided; no additional paper may be used. Your name
and Panther ID should be placed in three places; at the end of this paragraph to indicate acceptance of
all policies, on page 7 of the exam (Part B) and on your answer sheet. Use a number 2 pencil on answer
sheet and be sure to include the form of your exam on the answer sheet.
Name _________________________ Panther ID ____________
1.
Which reaction of an alkene proceeds with anti addition?
A)
Hydroboration/oxidation D)
Hydrogenation
B) Bromination E) Oxymercuration-demercuration
C) Oxidation with cold KMnO4
2.
Which of the following could not be used to synthesize 2-bromopentane efficiently?
A)
1-Pentene + HBr
B) 2-Pentene + HBr
C) 2-Pentanol + HBr
D)
2-Pentanol + PBr3
E) All of the above would afford good yields of 2-bromopentane
3.
Epoxidation followed by reaction with aqueous base converts cyclopentene into which
of these?
III III IV
H
OH
H
OH
H
OH
OH
H
H
OH
H
OH
O
H
H
A) I B) II C) III D) IV E) Equal amounts of III and IV
4.
Which of the compounds listed below would you expect to have the highest boiling
point? (They all have approximately the same molecular weight.)
A)
CH3CH2CH2CH2CH3 D)
CH3CH2CH2Cl
B) CH3CH2CH2CH2OH E) CH3CH2OCH2CH3
C) CH3CH2CH2OCH3
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Download Exam 3 with Answer Key - Organic Chemistry I | CHM 2210 and more Exams Chemistry in PDF only on Docsity!

CHM 2210: ORGANIC CHEMISTRY II Third Exam, Form 3 Section 02, Professor A. Herriott November 29, 2007

No electronic devices (calculators, cell phones, laptops, etc) may be used or consulted during the exam. All scrap work should be done on the extra page provided; no additional paper may be used. Your name and Panther ID should be placed in three places ; at the end of this paragraph to indicate acceptance of all policies, on page 7 of the exam (Part B) and on your answer sheet. Use a number 2 pencil on answer sheet and be sure to include the form of your exam on the answer sheet.

Name _________________________ Panther ID ____________

  1. Which reaction of an alkene proceeds with anti addition? A) Hydroboration/oxidation D) Hydrogenation B) Bromination E) Oxymercuration-demercuration C) Oxidation with cold KMnO 4
  2. Which of the following could not be used to synthesize 2-bromopentane efficiently? A) 1-Pentene + HBr → B) (^) 2-Pentene + HBr → C) (^) 2-Pentanol + HBr → D) (^) 2-Pentanol + PBr 3 → E) All of the above would afford good yields of 2-bromopentane
  3. Epoxidation followed by reaction with aqueous base converts cyclopentene into which of these?

I II III^ IV

H

OH

H

OH

H

OH

OH

H

H

OH

H

OH

OH

H

A) I B) II C) III D) IV E) Equal amounts of III and IV

  1. Which of the compounds listed below would you expect to have the highest boiling point? (They all have approximately the same molecular weight.) A) CH 3 CH 2 CH 2 CH 2 CH 3 D) CH 3 CH 2 CH 2 Cl B) CH 3 CH 2 CH 2 CH 2 OH E) CH 3 CH 2 OCH 2 CH 3 C) CH 3 CH 2 CH 2 OCH 3
  1. Select the structure of the major product formed in the following reaction. CH 3 CH

O

CH 2 HA

H 218 O

A) CH 3 CH 2 CH 218 OH D) CH 3 CH

OH

CH 2 (^18) OH B) CH 3 CHCH 3 (^18) OH

E) CH 3 CHCH 218 OH

(^18) OH C) CH 3 CHCH 2 OH

(^18) OH

  1. Addition of hydrogen chloride to the following molecule would produce:

Cl

I II III

Cl

Cl

Cl

Cl

Cl

Cl

Cl

Cl

IV V

Cl

Cl

HCl

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

  1. Which of the following reactions would have the smallest energy of activation? A) + Br. + HBr

B)

  • Br^. + HBr . C)
  • Br.. + HBr

D)

  • Br.. + HBr

E)

  • Br.. + HBr
  1. The bond dissociation energies for the relevant bonds are given below each of the species involved in the following reaction. Calculate the overall ∆H° for the reaction.

CH 3 CH 2 CH 2 - H + Br-Br CH 3 CH 2 CH 2 - Br + H-Br

∆Ho= 423 kJ/mol ∆Ho= 193 kJ/mol ∆Ho= 294 kJ/mol ∆Ho= 366 kJ/mol A) +616 kJ / mol D) +57 kJ kJ / mol B) -101 kJ / mol E) -44 kJ / mol C) -173 kJ / mol

  1. When 3- methyl-2-pentene is treated with mercuric acetate, Hg(O 2 CCH 3 ) 2 , in a THF- ethanol mixture and the resulting product reacted with NaBH 4 in basic solution, the principal product formed is which of these? A) 3-methyl-3-pentanol D) 2-ethoxy-3-methylpentane B) 3-ethoxy-3-methylpentane E) 1-ethoxy-3-methylpentane C) 3-methyl-2-pentanol
  2. What would be the major product of the following reaction?

I II III IV V

CH 3

CH 3

Br

CH 3 Br

CH 3

OR

CH 3

Br

CH 3

Br

HBr

peroxides

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

  1. cis-3-Methylcyclopentanol is treated with CH 3 SO 2 Cl in the presence of a base. The product of the reaction then is allowed to react with KI in methanol. What is the final product? A) trans-1-Iodo-3-methylcyclopentane D) 2-Methylcyclopentene B) cis-1-Iodo-3-methylcyclopentane E) 3-Methylcyclopentene C) 1-Methylcyclopentene
  1. Which alkene would yield only CH 3 CH 2 COOH on oxidation with hot alkaline potassium permanganate (followed by acid work-up)? A) (E)- 2-hexene D) (E)- 3-hexene B) (Z)- 2-hexene E) (E)- 4- methyl-2-pentene C) 2-methyl-2-pentene
  2. Which of the following can be described as “chiral, primary alcohol”? A) CH 3 CH 2 CH 2 CH 2 CH 2 OH D) (CH 3 ) 2 CHCHOHCH 3 B) (CH 3 ) 2 CHCH 2 CH 2 OH E) Two of the above C) CH 3 CH 2 CH(CH 3 )CH 2 OH
  3. Which of the reactions listed below would be exothermic? A) (^) H–H → 2H· B) (^) H· + CH 3 –H → CH 3 –H + H· C) (^) CH 3 · + CH 3 · → CH 3 –CH 3 D) (^) CH 3 · + CH 3 –H → CH 3 –H + CH 3 · E) All of the above
  4. Which product(s) would you expect to obtain from the following sequence of reactions?

CH 3

CH 3 OH

CH 3

OH

CH 3 H 3 C^ CH 2 OH O OH

enantiomer

enantiomer

enantiomer

I II III IV V

1. BH 3 -THF

  1. H 2 O 2 , NaOH

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

Answer Key

1. B

2. B

3. E

4. B

5. C

6. A

7. C

8. C

9. E

10. B

11. E

12. E

13. B

14. A

15. A

16. D

17. C

18. C

19. C

20. E

21. B

22. A