Sunteți pe pagina 1din 7

Chem 2312-003 Midterm II F12 !

Page 1 of 7

Chemistry 2312-003 Organic Chemistry I

Midterm Examination II
11:00 am 12:20 pm Answer Key

November 1, 2012 J. Jeon

Name: _______________Key_________________
please print

Total

/110

ID #: ______________________________________

There are 105 points on this exam and the seven exam pages. For the multiple choice questions 1-14, select the best answer and darken completely with a pencil the space corresponding to that answer in scantron (form # 882-E). You are free to use molecular models during the exam. For questions 15 and 16, I will not reconsider grades for answers written in pencil. Have fun!

Chem 2312-003 Midterm II F12 !

Page 2 of 7

1-2. (10 pts) These problems are about the IUPAC (International Union of Pure and Applied Chemistry) nomenclature of organic compounds. 1. (5 pts) Select the best name for the following molecule. a) (S)-5-Chloro-2,2-dimethylhexane b) (R)-2,2-Dimethy-5-chlorolhexane
Cl

c) (2S,5R)-2,2-Dimethy-5-chlorolhexane d) (2R,5S)-2-Chloro-5,5-dimethylhexane e) (R)-5-Chloro-2,2-dimethylhexane

2. (5 pts) Select the best name for the following molecule. a) (E)-3-Ethyl-5-fluorohept-5-ene b) (Z)-5-Ethyl-3-fluorohept-2-ene
F

c) (E)-5-Ethyl-3-fluorohept-2-ene d) (Z)-3-Ethyl-5-fluorohept-5-ene e) (E)-3-Fluoro-5-ethylhept-5-ene

3-6. (20 pts) Label each of the following pairs of structures as constitutional isomers (C), diastereomers (D), enantiomers (E), or superimposable (S). 3. (5 pts)
Cl EtO2C Cl CO2Et EtO2C Cl Cl CO2Et Me Br

4. (5 pts)
NH2 Me Me NH2 Br Me

a) C 5. (5 pts)
Me Me

b) D

c) E

d) S 6. (5 pts)

a) C

b) D

c) E

d) S

NH2 Me OH

H2N OH

a) C

b) D

c) E

d) S

a) C

b) D

c) E

d) S

Chem 2312-003 Midterm II F12 !

Page 3 of 7

7. (5 pts) Designate R or S configuration for each of the chirality centers (A, B, and C).
B A C OH N H Me Me

A a) b) c) d) e) R S S R S

B S S R R R

C S R S S R

8. (5 pts) Which of the following compound(s) is (are) meso?


Ph H H OH OH Ph same as H Ph OH Ph OH H Cl Cl H CH3 CH3 H

a) A b) B c) All d) none

9. (5 pts) Rank the following carbocations in order of stability. (1 = most stable, 4 = least stable) A 4 3 1 1 3 B 1 4 3 4 4 C 3 1 4 3 2 D 2 2 2 2 1

a) b) c) d) e)

10. (5 pts) Rank the following alkenes in order of stability. (1 = most stable, 4 = least stable) A a) b) c) d) e) 2 1 2 1 3 B 4 2 1 4 1 C 3 3 3 2 2 D 1 4 4 3 4

Chem 2312-003 Midterm II F12 !

Page 4 of 7

11-12. (5 pts) Consider the following reaction:


H H O + H Me !H (bonds broken) = 285 kJ/mol Br H O H H Me !H (bonds formed) = 381 kJ/mol + Br

The following rate equation has been experimentally established for this transformation: rate = k[HO][CH3CH2Br] The energy diagram for this transformation is shown below:

E H H O + H Me H O Br H H Me Reaction Coordinate + Br

11. Which of the following statements is not true? a) !G, !H, !S, and Keq are thermodynamic factors. b) The position of equilibrium will be significantly affected by an increase in temperature. c) The reaction is exothermic. d) The entropy of system is approximately zero. e) The reaction is spontaneous. 12. Which of the following statements is not true? a) Activation energy and temperature are kinetic factors. b) The rate will be faster by an increase in temperature. c) If the concentration of hydroxide is doubled, the rate will be doubled. d) The transition state is close in structure to the products. e) The reaction follows the second order kinetics.

Chem 2312-003 Midterm II F12 !

Page 5 of 7

13. (5 pts) Consider the following reaction.


HO H2SO4 products H2O

Me

Which of the following statements is not true? a) A mixture of substitution and elimination products is produced. b) The reaction is second order. c) The reaction mechanism involves a carbocation rearrangement. d) The reaction generates an intermediate. e) One of the products is produced as a racemic mixture.

14. (5 pts) What is the major product of the following reaction?


OH Br NaH

a)

OH

b)
Br

c)
O

d)

OH

e)

OH H

Chem 2312-003 Midterm II F12 !

Page 6 of 7

15. (15 pts) Draw the Major product and a detailed arrow-pushing mechanism (step by step, draw all the intermediates) for the following reactions in the boxes provided. Specify the correct stereochemistry where appropriate.
Br Me

NaOMe MeOH

Br Me H

Br NaOMe Me

Me thermodynamically more stable conformaiton kinetically active "reactive conformer"

Chem 2312-003 Midterm II F12 !

Page 7 of 7

16. (15 pts) Draw the Major product and a detailed arrow-pushing mechanism (step by step, draw all the intermediates) for the following reactions in the boxes provided. Specify the correct stereochemistry where appropriate.
Br Me

NaOMe MeOH

Br Me

Br Me Et Me

H Br

Et 180C H H Br Me Me NaOMe

Me Et Br H Me H Zaitsev product Et H Me Me

Et Hofmann product H Me Me

***** End of Exam ***** You may pick up your exam on Thursday, November 8 (in class). Thank you!

S-ar putea să vă placă și