Chemistry 232 – PRACTICE Midterm 2 – September / October 2010 – Your name: 1

________________________________

You will need to be able to show picture ID to take the test.

DO NOT OPEN THIS TEST UNTIL EVERYONE HAS ONE
I encourage following instructions:
ten (10) points will be deducted if items 1 to 4 below are not answered legibly.

1. Your name: 2. Lab section (if no lab say “no lab”)

3. Your ID number (last four digits are OK):

4. Your signature (required for grading):

Instructions:
1. In fairness to all, do not open this test until everyone has one.
2. Relax!! Put your TA’s name, your name, ID number and signature on this page.
3. This test is designed to last from 5:00 to 6:50 pm.
4. Nothing other than writing implements and a molecular model of ten atoms maximum are
allowed.
5. Problems 1-6 are multiple choice. Some problems may have more than one answer. Answers
are to be recorded on the test -- no Scantron needed.
6. If you finish early, quietly give the test to Grotjahn or a TA.

Problems 1-6 (4 points each) ________/24

Problem 7 ________/10
Problem 8 ________/6
Problem 9 ________/10
Problem 10 ________/10
Problem 11 ________/8
Problem 12 ________/10
Problem 13 ________/6
Problem 14 ________/10
Problem 15 ________/10
Problem 16 ________/8
Problem 17 ________/10
Problem 18 ________/10
Problem 19 ________/8
Problem 20 ________/10

TOTAL ________/150
Chemistry 232 – PRACTICE Midterm 2 – September / October 2010 – Your name: 2
________________________________

Note: problems 1-6 are multiple choice. Some can have one or two right answers. These
questions are indicated by "maximum of two." If you get both answers right, you get the full 5
points. If you pick one right answer only, you get 3 points. If you pick one right answer and other
wrong answer(s), or if you pick both right answers and wrong answer(s), you get zero points. So
don't over-guess!

1. What are the configurations of carbons 3 and 7 of the molecule below? The ketone carbon is
C2.
O
F3C
CH3
H CH3 H CH3

(A) 3R, 7S (B) 3R, 7R (C) 3S, 7S (D) 3S, 7R (E) none of the above

2. What is the configuration of C2 and C3 in the molecule below? C1 is the aldehyde carbon.

O H

HS H
H NH2
CH2OH

(A) 2R, 3S (B) 2R, 3R (C) 2S, 3S (D) 2S, 3R (E) none of the above

CH3
CH3
3. The compound at the right was used as a seasoning in antiquity.
How many chiral centers are in the compound?
O O
H3C O
(A) 7 (B) 6 (C) 5 (D) 4 (E) 3
OH

CH3
HO CH3
4. What functional group(s) are in the molecule at the right? O CH3
H3C
(Maximum of 2) CH3
O
(A) Amide (B) Ether (C) Ketone (D) Aldehyde (E) Ester
Chemistry 232 – PRACTICE Midterm 2 – September / October 2010 – Your name: 3
________________________________

5. A forensic chemist (chemist who deals with crime-related investigations) analyzed a sample of
a poisonous alkaloid (generic term for a naturally occurring nitrogen-containing molecule) and
determined that its specific rotation [] at 25 oC using sodium D light was +12 o. What can the
chemist properly conclude?

(a) there is one enantiomer in the sample

(b) the enantiomer present has the R configuration
(c) the sample is optically pure
(d) the butler did it
(e) none of the above

6. Select the correct ranking of the compounds shown according to their acidity.
"A > B" means A is more acidic than B.
O O O O
Cl C C C C
C OH H3C CH3 H2C OH H3C OH
Cl
Cl Cl
1 2 3 4

(A) 1 > 2 > 3> 4

(B) 1 > 3 > 4 > 2
(C) 1 > 3 > 2 > 4
(D) 2 > 4 > 3 > 1
(E) none of the above

7.
List the range of typical infrared absorptions for the following (in cm-1)
(a) carbonyl stretch
(b) alkane, C-H stretching
(c) hydroxyl group stretch
(d) a compound with molecular formula C3H6O showed key IR absorptions at 3300 (broad),
3050, 2960, and 1620 cm-1, among others. Given these data, propose the most likely
structure of the compound and briefly explain your answer.
Chemistry 232 – PRACTICE Midterm 2 – September / October 2010 – Your name: 4
________________________________

8.

Give correct IUPAC names for the following compounds.

(a)

(b)

9. Give correct IUPAC names for the following compounds.

(a)
CH2 OH

CH3 C
H
CH3

(b)

Br

Br

(c)

H CH3

H
HO
Chemistry 232 – PRACTICE Midterm 2 – September / October 2010 – Your name: 5
________________________________

10. For each of the following acid-base reactions, draw the products, on the lines provided
identify acid, base, conjugate acid and conjugate base, and predict whether equilibria will lie on
the side or products or reactants. Calculate or estimate Keq as 10 to some power.

(a) CF CO H (CH3)2NH +
3 2 +

(b) CH3CO2H + NaCl +

(c)
CH3MgBr + CH3OH +

Please note:
I told you in class that I expect you to have memorized the pKa of the following: (1) a very
strong acid, such as hydrochloric or sulfuric acid; (2) hydronium ion; (3) acetic acid; (4)
protonated amine; (5) water; (6) methane. With these numbers memorized, you can at least
estimate pKa values for related things like protonated methanol or trifluoroacetic acid using some
of the chemical principles we’ve learned about, for example using what you know about effects
of structure on acidity or basicity.
Chemistry 232 – PRACTICE Midterm 2 – September / October 2010 – Your name: 6
________________________________

11. Which are meso compounds? For molecules which can readily change their conformations,
assume that any meso conformation(s) are accessible through bond rotations.

NH2 COOH
H OH
CH3 CH3CH2 NH2
Br HO H
C C HO H
H3C H COOH
Br H CH3CH2 H
H
H OH

H
H Cl COOH CH2OH
CH3
H NH2 C C HO H H OH
H3C
Br Cl H H OH H OH

COOH COOH
Chemistry 232 – PRACTICE Midterm 2 – September / October 2010 – Your name: 7
________________________________

12. Draw the mirror images of the following molecules. Correctly identify the absolute
configuration of each chiral center in both the molecules shown and their mirror images. Are any
of these molecules superposable on their mirror image?

H2N OH Br

H
COOH
CH3 OH
HO H
CH3
CH OH H OH

CH3 H COOH

13. One chair form of the carbohydrate galactose is shown below. Draw the other chair form. If
the free energy change in going from the chair form shown to the other one is + 2.1 kcal per
mole, calculate Keq for the equilibrium at 25 oC.

OH OH

H2C H
O
H
HO
H
H OH
H OH
galactose
Chemistry 232 – PRACTICE Midterm 2 – September / October 2010 – Your name: 8
________________________________

14. Draw all the stereoisomers of 1,2-diaminocyclohexane. (The amino substituent is -NH2, e.g.
aminomethane would be CH3NH2.) Indicate which pairs of stereoisomers are enantiomers and
which are diastereomers. Correctly identify the absolute configurations of any chiral centers.

15. Consider trans-1-chloro-3-methylcyclohexane.

(A) How many stereocenters are in this compound?
(B) The compound undergoes reaction with zinc metal in the presence of acid to yield a new
compound. Draw the new compound, showing all stereochemistry, and name it.
(C) How many stereocenters are in the new compound?
(D) Which compound do you think would have the higher boiling point, the reactant or the
product? Briefly explain.
Chemistry 232 – PRACTICE Midterm 2 – September / October 2010 – Your name: 9
________________________________

16. Identify the relationships between the following structures.

(a) Br
Br

Br
Br

(b)
Br Br
Cl Cl

(c) HO H H OH

HN H HN H
CH3 CH3

(d) HO H H OH

H OH HO H
Chemistry 232 – PRACTICE Midterm 2 – September / October 2010 – Your name: 10
________________________________

17. Using correct arrow-pushing and Lewis structures, show the Brønsted-Lowry acid-base
reaction between water and 2-butyl cation (shown below). Make sure that the product is a
stable organic molecule satisfying the octet rule. If the pKa of the cation is - 8, on which
side will the equilibrium lie? Calculate the equilibrium constant.
H
H
C H
H
C C
H
H C H
H
H
2-butyl cation

18. Using correct arrow-pushing and Lewis structures, show the Lewis acid-base reaction
between water and 2-butyl cation. Draw all isomeric products which could be formed,
identify the relationship(s) between them, and also the ratio between them. Explain
briefly.
Chemistry 232 – PRACTICE Midterm 2 – September / October 2010 – Your name: 11
________________________________

19. Consider a single enantiomer of trans-1-methyl-3-tert-butylcyclohexane. (For this problem, it

does not matter which one.) There are two chair forms. Draw both of them. Which one is more
stable? Why?
Chemistry 232 – PRACTICE Midterm 2 – September / October 2010 – Your name: 12
________________________________

20. (a) Propose a structure for compound with the following IR spectrum and molecular formula
C5H12O, and briefly explain your choice.

(b) The IR absorption frequencies of the C-H bond in alkanes, alkenes and alkynes are
measurably different. Briefly explain why.

(c) For the following reaction sequence (it is not

1. DIBAL-H, ether
necessary to understand the chemistry) what CN 2. H2O, HCl CHO
significant change(s) would be expected by IR
(ignoring C-H absorptions)?
Chemistry 232 – PRACTICE Midterm 2 – September / October 2010 – Your name: 13
________________________________
Chemistry 232 – PRACTICE Midterm 2 – September / October 2010 – Your name: 14
________________________________