Chemistry 30A J. J.
Chang Spring 2013 Sample Midterm Note
Attached is a sample midterm for 30A from 2008. While the format for the actual midterm may vary, the concepts that will be tested are very similar.
Please omit the following as we have not covered/have placed a lesser emphasis on these concepts: 2C, 2E, 3D, 4B, 5D, 5E.
No calculators or notes will be allowed on the actual midterm. While I will not require you to compute formulae, I will expect you to set up equations and answer qualitative questions regarding Gibbs energy/specific rotations.
Chemistry 30A UCLA Summer 2008 Midterm Exam
On my honor, I have neither given nor received any aid on this exam Signature: Name: UCLA Student I. D. Number:
Question Points ------------------------------------1 (8) ------------------------------------2 (32) ------------------------------------3 (17) ------------------------------------4 (21) ------------------------------------5 (22) ------------------------------------Total (100)
Chemistry 30A, Summer 2008 Page 1
Name:
1. (8) Answer questions A-H below relative to the structure of tetracycline (a common antibiotic agent). The lettered arrows in the structure refer to the questions.
B C
HO CH3 H N H OH O
D H
HO
O HO
OH O
NH2
A. (1) What type of carbon (primary, etc) is this carbon atom?
_________________
B. (1) What orbitals does this carbon atom use for bonding? ___________________ C. (1) What is the name of this functional group? ____________________________ ____________________
D. (1) What is the geometric descriptor for the ring fusion? E. (1) What is the chirality (R or S) at this position?
_________________ ____________________
F. (1) What orbitals does this carbon atom use for bonding? G. (1) What is the name of this functional group? H. (1) What is the name of this functional group?
____________________________ ____________________________
Chemistry 30A, Summer 2008 Page 2 2. (32) A. (4) Name the following compound using IUPAC rules.
Name:
B. (4) Name the following compound using IUPAC rules.
C. (4) Name the following compound using IUPAC rules.
Cl
D. (4) Draw the structure of 5-tert-butyl-3-ethyl-6-isopropylnonane.
E. (4) Draw the structure of (1S, 3S, 4R)-1-chloro-4-ethyl-3-methylcyclohexane.
F. (4) Write a balanced equation for the complete combustion of cyclopropane.
G. (8) Draw THREE resonance structures for the following anion and CIRCLE the best resonance contributor (lowest energy).
N O
Chemistry 30A, Summer 2008 Page 3
Name:
3. (17) A. (6) Draw three Newman Projections for the staggered conformations about the bond indicated in the following molecule and label them X, Y, Z.
B. (2) Which conformation (X, Y, or Z) is expected to have the lowest energy?
C. (3) Draw the one Newman Projection for the HIGHEST energy ECLIPSED conformation and label this W.
D. (6) Draw the Potential Energy Diagram for rotation about the bond indicated in part 3A. Clearly label where W, X, Y, and Z occur.
Chemistry 30A, Summer 2008 Page 4
Name:
4. (21) A. (6) Draw two chair conformations for the following molecule and label them A and B.
t-Bu Me
Br
B. (6) Calculate the equilibrium ratio of conformers for the compound above and list the %A and %B. Group A-value G = -RT(LnK) CH3 1.7 kcal/mol K = e(-G/RT) Br 0.6 kcal/mol T = 298 deg t-Bu 5.0 kcal/mol R = 1.987x10-3 kcal/mol deg
C. (3) The specific rotation for (S)-(+)-ibuprofen is +59. What is the specific rotation for (R)-(-)-ibuprofen? D. (3) What is the observed rotation for a 90 : 10 mixture of (S)-(+)-ibuprofen and (R)-(-)ibuprofen? E. (3) What would be the observed rotation for a 60% ee sample of (S)-(+)-ibuprofen?
Chemistry 30A, Summer 2008 Page 5
Name:
5. (22) A. (3) How many stereoisomers are possible for a structure with 4 stereogenic centers? B. (6) Label each pair of structures as ENANTIOMERS, DIASTEREOMERS, or MESO.
HO CHO H CH2OH OH H CHO OH CH2OH OH
HO
HO
OH
OH
OH
OH
Br
Br
C. (2) Draw a Lewis Structure for formaldehyde imine which has the molecular formula CH2NH.
D. (8) Draw the molecular orbital diagram for the Valence Electrons in formaldehyde imine. Include the electron occupancy of the orbitals.
E. (3) Draw the Fischer projection for the following molecule.
Cl Me Br Pr
