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Chem 2312-003 Midterm I F13 !

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Chemistry 2312-003 Organic Chemistry I

Midterm Examination I
11:00 am 12:20 pm

September 26, 2013 J. Jeon

Name: ___________Answer Key______________


please print (last, first)

Total

/105

ID #: ______________________________________

There are 102 points on this exam and the four exam pages. For the multiple choice questions 1-15 (each 7 pts), select the best answer and darken completely with a pencil the space corresponding to that answer in scantron (form # 882E).

You are free to use molecular models during the exam. Have fun!

Chem 2312-003 Midterm I F13 !

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1. (7 pts) Select the major resonance contributor. a) 1a


H3C N H

H3C

N H

b) 1b c) same

1a

1b

2. (7 pts) Select the best explanation regarding your choice above (1a vs. 1b in question 1). a) charges b) octet rule c) atom size d) electronegativity e) molecular geometry

3-4. Questions 3 and 4 are about isomerism. 3. (7 pts) What is the relationship of the following pairs (3a and 3b)?
H Et H OH H Et OH H

a) constitutional isomers
OH Et OH Et

b) conformational isomers c) enantiomers d) diastereomers e) identical

3a

3b

(1R,3S)-3-ethylcyclohexanol (1R,3R)-3-ethylcyclohexanol

3a

3b

! these molecules have same connectivity (constitution). ! conformational isomerism occurs within the same molecule, which has a temporarily different three-dimensional shape. ! enantiomers are nonsuperimposable mirror images. ! diastereomers are nonsuperimposable and not mirror images. ! example of enantiomers
Et OH HO Et Et OH

H Et

H OH HO

H H Et

4. (7 pts) What is the relationship of the following pairs (4a and 4b)? a) constitutional isomers
OH Me OH Me meso Me OH Me OH 90 rotation OH Me OH Me 120 rotation OH HO Me Me

b) conformational isomers c) enantiomers d) diastereomers e) identical (Also I give a credit for this.)

4a

4a
identical but conformational isomer

4b

Chem 2312-003 Midterm I F13 !

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5. (7 pts) What is the total number of stereoisomers possible for the compound 5?
Me Me * OH * Me

a) 3
Me Me OH Me Me Me OH Me Me Me OH Me
2

Me Me

OH Me

b) 4 c) 5 d) 6 e) 7

2n = possible stereoisomers (n = chirality center), 2 = 4

6. (7 pts) How many ! bonds are in acetylene 6?


H H

a) 1 b) 2 c) 3 d) 4 e) 5

1 " and 2 ! bonds in a triple bond

7. (7 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 7. a) (4S,6R)-2,4,6-Trimethyloctane
8

b) (4R,6S)-2,4,6-Trimethyloctane c) (2S,4R)-2-Ethyl-4,6-diimethylheptane d) (2R,6S)-6-Ethyl-2,4-diimethylheptane e) (2R,4R,6R)-2-Ethyl-4,6-diimethylheptane

Me Me

Me

Et Me
H3C
1

Me

Me (R)

CH3 H CH3

8. (7 pts) The following molecules, 8a and 8b, contain chirality centers. Which of the following compound(s) is (are) optically inactive? (find meso compounds)
Cl H HO OH Cl OH OH H H Cl OH same as Cl OH H Cl OH same as H Cl H OH

2a

2b

2b

2b

a) 8a b) 8b c) all

then
Cl H HO OH H Cl OH OH H H Cl same as Cl OH OH H Cl same as OHCl H OH

d) none

2a

2b

2b

2b

Chem 2312-003 Midterm I F13 !

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9-11. Consider the molecule butane, viewing the C2-C3 bond.


6 kJ/mol Me H H
2

11 kJ/mol 3.8 kJ/mol Me H H 4 kJ/mol Me H


2

H Me H H H Me 6 kJ/mol
2

MeMe
2

H H 4 kJ/mol

H 4 kJ/mol H

Me

9a
anti most stable

9b
eclipse

9c
gauche

9d

eclipse Interaction Energy cost (KJ/mol)

same Me H
2

Me H H

Me H
2

Me H H

Me H
2

H H Me

Me H
2

H H methyl/methyl gauche methyl/H eclipse methyl/methyl eclipse H/H eclipse 3.8 6.0 11.0 4.0

Me

9e

9f

9g

9h

Me H H
2

H Me Me H H H
2

Me H

9. (7 pts) Which of the following conformers (i.e. conformational isomers), 9a to 9d, is in the highest energy? a) 9a b) 9b c) 9c d) 9d

Based on the table, two eclipsed conformations. But, 9d is in a higher energy level. 10. (7 pts) Based on the table regarding energy costs, what is the total energy cost of the conformation 9f? a) 0.0 KJ/mol b) 9.8 KJ/mol c) 3.8 KJ/mol d) 19 KJ/mol e) 16 KJ/mol

11. (7 pts) Match the same conformers (i.e. conformational isomers)? a) 9a and 9h b) 9b and 9g c) 9c and 9e d) 9d and 9f e) none

Chem 2312-003 Midterm I F13 !

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12. (7 pts) The following acid-base (proton transfer) reaction is in equilibrium. Which of the following statements is correct?
Me Me

a) H in 12a is less acidic than H in 12b.


Oxygen stabilizes anion better than nitrogen due to a electronegativity of atoms; the corresponding acid (H ) is more acidic. (H2O vs NH3)

Ha

NH

Hb

NH

b) Keq is [12a]/[12b].

Keq = [12b]/[12a].

12a

12b

c) None of 12a and 12b contains a chirality center. one each d) This is an intermolecular proton transfer reaction.
intramolecular

e) The reactants 12a will be favored at equilibrium (Keq > 1).


equilibrium rises toward more stable anion.

13. (7 pts) Chair conformations of dimethylcyclohexanes, 13a to 13d are presented below as Newman projections. Select the most stable conformation.
1,3-diaxial interaction equitorial Me H H
1 2

H equitorial Me H H H

H equitorial Me H H H H

H H H H H

Me axial H H H

axial Me

Me

Me axial

axial Me

1,3-diaxial interaction

1,3-diaxial interaction

1,3-diaxial interaction

13a

13b

13c

13d

a) 13a

b) 13b

c) 13d

d) 13d

14. (7 pts) Consider two bolded hydrogens, H and H in compound 14. Select the hydrogen with the lower pKa (i.e. more acidic).
CF3 Ha Hb CH3

a) Ha b) Hb c) same Ha is closer to electronegative atoms (CF3) than Hb. d) none

14

15. (7 pts) Select the best explanation regarding your choice above (in question 5). a) atoms (bearing the charge) b) atom size c) resonance d) inductive effect (through " bond) e) orbitals

***** End of Exam *****