Chem 2312-003 Midterm I F12 !

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Chemistry 2312-003 Organic Chemistry I

Midterm Examination I
11:00 am 12:20 pm

September 25, 2012 J. Jeon

Name: ____________________________________
please print

Total

/100

ID #: ______________________________________

There are 100 points on this exam and the six exam pages. For the multiple choice questions 1-20, 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. Have fun!

Chem 2312-003 Midterm I F12 !

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1. (5 pts) Five atoms in the molecule below are labeled as A to E. Which of the following is correct regarding i) valence, ii) hybridization, iii) electronic arrangement of the each numbered atom? i) valence ii) hybridization sp2 sp sp3 sp2 sp2 iii) electronic arrangement bent linear trigonal planar tetrahedral trigonal planar

H B

E
N H

D
!

C B

a) b) c) d) e)

A B C D E

3 3 4 3 3

2. (5 pts) Which statement concerning the length of bonds indicated in the molecule below is correct?
H B H

a) II is the shortest and I is the longest

I
N H

III
O

b) II is the shortest and III is the longest c) III is the shortest and II is the longest d) III is the shortest and I is the longest
!

II

e) I is the shortest and III is the longest

3. (5 pts) The dipole moments (if any) of each of the following molecules are given. Which of the following is not correctly indicated.
a) b) c) d)

F F

O C O

4-9. Questions 4/5 and 6/7 are related to each other. 4. (5 pts) Select the major resonance contributor.
Br O N CH3 Br O N CH3

a) 1a b) 1b c) same

1a

1b

5. (5 pts) Select the best explanation regarding your choice above (1a vs. 1b in question 4). a) charges b) octet rule c) atom size d) electronegativity e) molecular geometry

Chem 2312-003 Midterm I F12 !

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6. (5 pts) Select the major resonance contributor.

CH3 H2C N H H2C CH3 N H

a) 2a b) 2b c) same

2a

2b

7. (5 pts) Select the best explanation regarding your choice above (2a vs. 3b in question 6). a) charges b) octet rule c) atom size d) electronegativity e) molecular geometry

8-10.

Question 8 to 10 are about isomerism.

8. (5 pts) What is the relationship of the following pairs (3a and 3b)? a) constitutional isomers
O H F H3C H3C O H F

b) conformational isomers c) enantiomers d) identical

!

H3C

CH3

3a

3b

e) cis-trans isomers

9. (5 pts) What is the relationship of the following pairs (4a and 4b)? a) constitutional isomers
Cl NH2

b) conformational isomers c) enantiomers

Cl

H2N

d) identical
!

4a

4b

e) cis-trans isomers

10. (5 pts) What is the relationship of the following pairs (5a and 5b)?
CH3 H H Cl H Cl

a) constitutional isomers
CH3 H

b) conformational isomers c) enantiomers d) identical

!

5a

5b

e) cis-trans isomers

Chem 2312-003 Midterm I F12 !

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11. (5 pts) Select the molecule with the lowest pKa (6a and 6b).
H P CH3 CH3 vs. P H CH3 CH3

a) 6a b) 6b c) same

6a

6b

12. (5 pts) Select the best explanation regarding your choice above (in question 11). a) electronegativity of atoms b) atom size c) resonance d) inductive effect e) orbitals

13. (5 pts) Acid-base (proton transfer) reaction is shown below. Which of the following statements is correct?
O HO CH3 + H O H O O CH3 + H O H H

10

a) 8 is acid b) 10 is base c) the reactants will be favored at equilibrium (Keq < 1). d) the products will be favored at equilibrium (Keq > 1). e) this reaction is completely at equilibrium (Keq = 1). 14. (5 pts) This problem is about the IUPAC (International Union of Pure and Applied Chemistry) nomenclature of organic compounds. Select the best name for the following molecule 11. (ignore the relative stereochemistry.) a) (4-Cyclopropyl-3-ethyl-5-methyl)octane b) (3-Ethyl-5-methyl-4-octyl)cyclopropane c) (6-Ethyl-5-cyclopropyl-4-methyl)octane d) (5-Cyclopropyl-6-ethyl-4-methyl)octane

11

e) (6-Ethyl-4-methyl-5-octyl)cyclopropane

Chem 2312-003 Midterm I F12 !

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15-17. Two chiral cyclohexanes, 12 and 13 are presented below as Newman projections and chair conformations. (FYI, steric hindrance from 1,3-diaxial interactions of OH/H, Me/H, and Et/H are 4.2, 7.6, and 8.0 kJ/mol respectively.)
OH
1 2

H3C H3C

Me Me

OH
1 2

Et

Et

12
Et H H H
1 2

13
H OH
1 2

Me Me

H OH Me H

Me Me

Me Et

OH
1 2

Me Me Et

H OH
1

H Et H

12a

12a

13a

13a

H Et H
2 1

OH Me Et H Me

Me
2

OH

Me
2

OH H
1

OH Me

Me

Me Et

2 1

H Me

Et

12b

12b

13b

13b

15. (5 pts) Select more stable conformation between 12a and 12b, which are ring-flipped isomers. a) 12a b) 12b c) identical

16. (5 pts) Select more stable conformation between 13a and 13b, which are ring-flipped isomers. a) 13a b) 13b c) identical

17. (5 pts) Based on the conformational analysis above, which structure (12 vs. 13) is lower in energy? a) 12 b) 13 c) identical

Chem 2312-003 Midterm I F12 !

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18-20.

Consider the molecule pentane, viewing the C2-C3 bond.

Me H Me H
2

Me Et H
2

Et Me
2

H H

Et A

H Et

H H

H H

H H

H B C

Interaction

Energy cost (KJ/mol)

D
Potential Energy

B
? methyl/methyl gauche methyl/ethyl gauche methyl/H eclipse ethyl/H eclipse methyl/methyl eclipse methyl/ethyl eclipse H/H eclipse 120 180 Dihedral Angle 240 300 3.8 4.2 6.0 6.4 11.0 12.0 4.0

C A
60

18. (5 pts) Which of the following conformations is the least stable conformation? a) A b) B c) C d) D e) all

19. (5 pts) Based on the table regarding energy costs, what is the total energy cost of the conformation C? a) 3.8 KJ/mol b) 4.2 KJ/mol c) 12 KJ/mol d) 15.8 KJ/mol e) 16.4 KJ/mol

20. (5 pts) Based on the table regarding total energy costs, what is the total energy cost of the conformation D? a) 12 KJ/mol b) 15.8 KJ/mol c) 16.4 KJ/mol d) 17.4 KJ/mol e) 20 KJ/mol

***** End of Exam ***** You may pick up your exam on Tuesday, October 2 (in class).