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3rd Midterm

Dr. Shabbir Ochem I

11-14-13

Name________________________________________________

Signature____________________________________________

UT EID ________________________________________________

Please print the first three letters


of your last name in the three boxes

Reminders:
You must have ALL your answers written in permanent ink in order to get a regrade.
Please dont write in RED.
You must have your valid UT ID card (or other government-issued ID) with you. You
will need to show it to the proctors when you turn in your exam.
Cell phones are not allowed during your exam. Please have your cell phone silenced and
away from your person before the exam (not in your pockets).
We will randomly ask students to relocate before the exam.
We routinely Xerox a number of exams after initial grading to guard against receiving
altered exams during the regrading process.
Some of your fellow students will be taking this midterm exam late, so it is not to be
discussed with ANYONE in ANY form (including but not limited to verbal discussion,
text messages, email, facebook posts, etc.) until Friday at 5pm. Discussing the content of
the exam before this time constitutes academic dishonesty.

3rd Midterm

Dr. Shabbir Ochem I

11-14-13

University Code of Conduct:


The core values of The University of Texas at Austin are learning, discovery, freedom,
leadership, individual opportunity, and responsibility. Each member of the university is
expected to uphold these values through integrity, honesty, trust, fairness, and respect
toward peers and community.

__________________________________________
Your Signature

3rd Midterm

Dr. Shabbir Ochem I

11-14-13

3rd Midterm

Dr. Shabbir Ochem I

11-14-13

Q1- (4 points each) Write the IUPAC names of the following molecules on the lines
provided. Include R or S and E or Z designation where appropriate.

Cl

Cl

Br

CH3
CH3

Q2- (4 points) Provide a line drawing of the following IUPAC named compound.
(R)-1-bromo-6-methyl-1-cyclohexene

Points__________________________

3rd Midterm

Dr. Shabbir Ochem I

11-14-13

Q3- (8 points) Circle the molecule with the highest boiling point. In the box provided,
write the letter of the phenomena (A, B, or C) that best explains your answer.
A) Vander Waals Forces

B) Hyperconjugation

1)

2)

Cl

vs

Br

vs

Br

C) Dipole Moment

Q4- (4 points) Rank the following carbon radicals according to their relative stability
from 1 to 4, where 1 is the most stable and 4 is the least stable.

Q5- (2 points) Circle the molecule with the strongest C-H bond (indicated with H
explicitly).

H
H
Q6- (2 points) Label the two bonds between the two carbons. Specify which p-orbitals
are involved in the formation of the individual bonds, for example px, py or pz.

!
H C

C H

Points__________________________

3rd Midterm

Dr. Shabbir Ochem I

11-14-13

Q7- (2 points) The two constitutional isomers shown below are in equilibrium with each
other. This type of isomerism is called ___________________________.
H

O H

C C
H 3C

C
CH 3

O
C
H

Q8 (a)- (10 points) Draw two reaction coordinate diagrams on the same plot for the
exothermic creation of the two carbon-centered radicals shown. Show the relative
energies of the radicals and place the transition states in these diagrams at the appropriate
place along the reaction coordinate. Label whether they are both late or early transition
states and draw the structures of the reactants and products in the appropriate places on
the diagram.
Cl

HCl

Cl

HCl

Energy

Reaction Coordinate

Q8 (b)-(2 points) The transition state theory called _____________________________


explains why radical chlorination of alkanes is not as regioselective as compared to
radical bromination of alkanes.

Points__________________________

3rd Midterm

Dr. Shabbir Ochem I

11-14-13

Q9- (4 points each) Fill in the boxes with the products of the following reactions. Draw
only the MAJOR product or products and indicate stereochemistry. When a racemic
mixture is formed, you must draw both enantiomers and write racemic in the box.

H2
Lindlar's
Catalyst

Br 2
h!

NBS
h!

HBr, H 2O2

Points__________________________

2 moles HCl

3rd Midterm

Dr. Shabbir Ochem I

11-14-13

Q9- (4 points each) Fill in the boxes with the products of the following reactions. Draw
only the MAJOR product and indicate stereochemistry. When a racemic mixture is
formed, you must draw both enantiomers and write racemic in the box.

HgSO 4
H 2SO4, H 2O

Na
NH 3(l)

1) (sai) 2BH
2) H 2O2, NaOH

1) NaNH 2
2) CH3I

Br

2 moles NaNH 2
Br

Points__________________________

3rd Midterm

Dr. Shabbir Ochem I

11-14-13

Q9- (4 points each) Fill in the boxes with the products of the following reactions. Draw
only the MAJOR product and indicate stereochemistry. When a racemic mixture is
formed, you must draw both enantiomers and write racemic in the box.

H 2 /Pd

1) OsO4
2) NaHSO 3

1) O3
2) (CH 3 )2S

2 moles Cl2

1) BH 3
2) NaOH/H 2O2

Points__________________________

3rd Midterm

Dr. Shabbir Ochem I

11-14-13

Q10- (4 points each) Fill in the boxes with the reactant of the following sequence of
reactions. When a racemic mixture is formed, you must draw both enantiomers and write
racemic in the box.

1 mole of NaNH 2

CH3Br

Na, NH 3(l)

1) O3
2) (CH 3 )2S

O
H

Points__________________________

10

3rd Midterm

Dr. Shabbir Ochem I

11-14-13

Q11- (4 points each) Write the products of the following sequence of reactions. Show the
MAJOR product for each reaction. If you create a racemic mixture draw both the
enantiomers and write racemic.

Cl2

2 moles of NaNH 2

H2
Lindlar Catalyst

NBS, h!

Product

Points__________________________

11

3rd Midterm

Dr. Shabbir Ochem I

11-14-13

Q12-(17 points) Use arrows to move electrons for the following mechanism. Show all the
lone pairs, formal charges and all the products you make in each step. For the products
that are generated in a racemic mixture, draw both enantiomers and write racemic.

CH 3
H 3C

Na

CH
CH 3

Na

Product

Points__________________________

12

3rd Midterm

Dr. Shabbir Ochem I

11-14-13

Q13 (a) (18 points) Use arrows to move electrons for the following reaction mechanism.
Show all lone pairs. For any products that are generated in a racemic mixture, draw both
enantiomers and write racemic.
Inititation
R

Br

O R

H +

Propagation
H

C
H

CH3

Br

Product
Q13 (b) (4 points) Explain why the termination steps in this reaction are a rare event.

Points__________________________

13

3rd Midterm

Dr. Shabbir Ochem I

11-14-13

Q14-(14 pts) Synthesis question. Show how the starting material can be converted to the
product through any of the reactions you have learnt in O. Chem. I. Show all the reagents
you need and indicate the stereochemistry when appropriate. You do not need to show
arrow pushing like in a mechanism question, only the reactions. If a racemic mixture is
formed draw both enantiomers and write racemic next to the two structures. All carbon
atoms should come from the same starting material. Use as many molecules of the
starting material as you might need to get to the product.

Points__________________________

14

3rd Midterm

Dr. Shabbir Ochem I

11-14-13

Q15 (18 pts) Synthesis question. Show how the starting material can be converted to the
product through any of the reactions you have learnt in O. Chem. I. Show all the reagents
you need and indicate the stereochemistry when appropriate. You do not need to show
arrow pushing like in a mechanism question, only the reactions. If a racemic mixture is
formed draw both enantiomers and write racemic next to the two structures. All carbon
atoms should come from the same starting material. Use as many molecules of the
starting material as you might need to get to the product.

Points__________________________

15

3rd Midterm

Dr. Shabbir Ochem I

Total
Points
16

16

14

20

20

20

10

12

11

16

12

17

13

22

14

14

15

18

Total

205

Page

Earned
Points

11-14-13

16