1st Midterm

Shabbir 320M/328M

06-16-14

Name________________________________________________

Signature____________________________________________

UT ID ________________________________________________

Please print the first three letters

of your last name in the three box

Reminders:
You must have your answers written in Permanent Ink in order to get a regrade.
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 give your proctors your
cell phone before the exam
We would ask students to randomly move before the exam. (Do I need to add this
and I think it needs to be reworded)
We routinely Xerox a Number of Exams after initial grading to guard against
receiving altered exam during the regarding 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 post etc) until Friday at 5pm.
Discussing the content of the exam before this time constitutes academic
dishonesty.

Points___________________________________

1st Midterm

Shabbir 320M/328M

06-16-14

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

Points___________________________________

1st Midterm

Shabbir 320M/328M

06-16-14

Q1- (4pt) Write the IUPAC name of the following line structures. Label R and S
while naming.

(S)-6-ethyl-2,3-dimethyloctane

__________________________________________________________________
Q2- (4pt) Draw the line structure of the following molecule.
cis-1,2-Diethylcyclobutane

Q3- (4pt each) Add lone pair of electrons where necessary to complete the
valence shell of atom in these molecules. Then assign formal charges as
appropriate?

A)
H

B)
C

H
O H

D)

C)
H

C
H

1 Points___________________________________

1st Midterm

Shabbir 320M/328M

06-16-14

Q4- (2pt each box) Write the hybridization of the following.

sp3

sp2

sp2

sp3
sp3

N
C

H
H

O
O
HO

Penicillin G
sp2
sp2

sp2
sp2
Q5- (4pts for each box) Describe each bond indicated with an arrow as an overlap
of molecular orbital for example an answer might be ( Csp3-Csp3)
Csp - Csp2

H
H

C
H

Csp2 - H1s

C
C

C
H

Csp 3 - Csp2
C2p - C2p2

Points___________________________________
2

1st Midterm

Shabbir 320M/328M

06-16-14

Q6- (4pts for each box) Name the functional group of each compound in the box
provided.

A)
H

B)

H
H

OH

D)
H

Amide

Carboxylic Acid

C) H

H
Aldehyde

Ester

Q7- (4pts each) For each that is polar specify the direction of the bond dipole
moment with a sign
. Additionally if there is an overall direction of the
dipole moment indicate it with the sign

A)

B)

O
H
H

C)

C
H

H
C

D)

H
Cl

on the left side of the molecule?

F
Cl

Cl

Points___________________________________
3

1st Midterm

Shabbir 320M/328M

06-16-14

Q8- (5pt each) Draw the resonance structure of the following molecule. Use
arrows to show the movement of electrons to give the structure you drew. Assign
formal charges as appropriate. Additionally if one of the two contributing structure
make a major contribution to resonance draw a circle around the major
contributor.

C O C C
H

H
H

C
H

H
C
H

H
N
C
H

H N C O

C O C C
H

O H

C
H

H
H

H
H

O H

H
C

H
C
H

C
H

N
C
H

H
H

H N C O

Points___________________________________
4

1st Midterm

Shabbir 320M/328M

06-16-14

Q9- (4pt for each box) The following molecules are described as a hybrid of three
contributing structures Draw the second and the third contributing structure
include all the formal charges and lone pairs. Use arrows to show the movement
of electrons to give the structure you drew?

H
H

C
H

N
C

N
C

C
H

H
H

N
C

Q10- (10pts) The following compound is Lovastatin. It is used to lower cholesterol

Label every chiral center in this molecule with an ASTERISK *?

HO

Lovastatin

How many stereoisomers are present in Lovastatin? _________2 _______________

Points___________________________________
5

1st Midterm

Shabbir 320M/328M

06-16-14

Q11-(5pt) The following compound is called S-Naproxen and is the active

ingredient in the pain killer Naprosin. State how you would experimentally
distinguish this compound from its R-Naproxen.
Hint: Remember the man with the string tied to the wall J
H

CH 3

(S)

CO2H

O
The two enantiomers would rotate the plane-polarized light in the opposite
direction. Therefore experimentally you can distinguish S-Naproxen from RNaproxen.

Q12- (8pts each) For each of the following molecule circle the one is more stable?
Justify your answer by marking an X next to the kind of strain present in the
unstable molecule?
CH3
H

H 3C CH 3

vs

Angle
Strain
H
H

H
H

CH3
F

Tortional
Strain

Steric
Strain

I
I

F
F

vs
I

vs

Points___________________________________
6

1st Midterm

Shabbir 320M/328M

06-16-14

Q13- (10 pts) Draw a Newman projection for each conformations of the molecule
drawn below (bromoethane). Also draw the corresponding energy curve. Be label
the energy diagram and indicate which conformation belongs to which energy
level. Define 0 dihedral angle as your highest energy point in the diagram.
H
H
H

H
Br

bromoethane

HBr
H
H

HH

H
H

HBr
H
H

HH

HH

H
H

Energy

HH

HBr

HBr

Br

120 O

Br

H
H

H
60O

Br

180 O

240O

300O

360O

Dihedral Angle

Points___________________________________
7

1st Midterm

Shabbir 320M/328M

06-16-14

Q14- (10pts) Using cartoon representation draw a molecular orbital mixing

diagram for C-C bond. In your picture consider the relative energies of the C
atomic orbitals and the resulting molecular orbitals. Label all the atomic and the
molecular orbital.

Energy

Anti Bonding Molecular Orbital

C 2p

C 2p

Bonding Molecular Orbital

Points___________________________________
8

1st Midterm

Shabbir 320M/328M

06-16-14

Q15- (5pt each) For each of the molecules drawn state their relationship to each
other. Whether they are diastereomers, enantiomers, same molecule or
constitutional isomers. Circle the all meso compounds.
CH 3

H 3C CH 3

CH 3
H

(S)

C
H

H
H

H 2C

H
H 2C

Diastereomers

vs

vs
CH2CH 3
OH

(S)

HO

Same Molecule

CH
C

CH2CH 3
H

O
H

vs

Constitutional Isomers

OH H

H 3C
H

(S)

CH 3
vs

(R)

CH 3

HO

OH

(R)

HO

HO

OH
(R)

H 3C

(S)

HO
vs

(S)

CH 3

Enantiomers

CH 3
H

(S)

Diastereomers
OH

(S)

Points___________________________________
9

1st Midterm

Shabbir 320M/328M

06-16-14

Q16- (9pt) Draw the chair conformation of the following molecule. Circle the most
stable conformer. If there is no difference in stability between the two conformer
do not circle either chair conformers. Label the chiral centers R or S in the
molecule.
OH
CH 3

H 3C
=

(R) (R)

H 3C

CH 3

HO

(R)
(R)

(R)

OH

(R)

H 3C

CH 3

Q17- (3pt) Circle the molecule that has the lowest boiling point.

vs

Q18- (4pt each box) Label the following compounds R or S. If there is no chiral
center, write A for ACHIRAL
Cl
H
O
C
OH
OH
H 3C

HO

(R)

(R)

(R)

CH 3 O

HO
H 3C

C
H
(R)

CH 3 H

HO
N

CH 3 H

H 3C

H
A
Points___________________________________

10

1st Midterm

Shabbir 320M/328M

Page

Earned
Points

Total
Points
24

34

32

15

18

29

10

10

25

10

32

Total

229

06-16-14

Points___________________________________
11