Chem 230 (Fall 2013)

Final Exam
Name______________________________________________________ ID __________________
Section___________________

TA________________________________________

Problem 1 (20 pts)_____________

Problem 2 (20 pts)_____________
Problem 3 (20 pts) _____________
Problem 4 (20 pts)_____________
Problem 5 (20 pts)_____________
Problem 6 (20 pts)_____________
Problem 7 (20 pts)_____________

TOTAL (140 pts)___________________

Page 1
1a.

Rank the following compounds by acidity. 4 = most acidic; 1= least acidic (5 pts)

Cl

Cl

1b.

Rank the following compounds by their order of reactivity in E2 reaction using a large base,
i.e. t-BuOK. 4 = most reactive; 1= least reactive (5 pts)

Cl

1c.

SH

OH

OH

OH

Cl

Br

Br

Rank the following compounds by their order of reactivity in SN1 reaction. 4 = most reactive; 1=
least reactive (5 pts)

Cl

Br

Cl

Br

1d.

Rank the following compounds by their order or basicity. 4 = most basic; 1= least basic (5 pts)

LiH

KH

LiAlH4

NaBH4

Page 2
2a.

A student wanted to synthesize methyl tert-butyl ether, CH3OC(CH3)3. He attempted the

synthesis by adding sodium methoxide to tert-butyl chloride, but he obtained none of the desired
product. Show the product that is formed in this reaction and propose a better synthesis of methyl
tert-butyl ether from any other starting materials. (10 pts)

2b.

Explain why compound A reacts with potassium tert-butoxide much faster than compound B and
predict the structure of the product of this reaction. (10 pts)
Br

H
A

Br

H
B

3.

Page 3
Provide products of the following reactions and their detailed mechanisms. All reagents are used
in stoichiometric amounts (10 pts each).

OH

Na2Cr2O7
H2SO4, H2O

Br2
h!

Page 4
4.
(a)

Predict products of each of the following reactions. (20 pts).

O

NaBH4
excess
OH

t-BuOK
excess
DMF

EtOH

OH

(c)

Br

(b)

PCC
excess

NaOH
excess

(d)
Me

SMe

CH2Cl2

H2O

OH

(e)

NADH

O
OH
O

MeLi
(1 equiv.)

(f)

(1 equiv.)
lactate
dehydrogenase

OH

OH

diethyl ether

H2O

(g)

Br

(i)

Br

LiAlH4
excess

Cl

MeNH2
(1 equiv.)

DMF

NaOMe
excess
MeOH

diethyl ether;
followed by
D2 O

NaHCO3
Br

(h)

(j)

HBr
(1 equiv.)
hexane

Page 5
5a.

Predict major products of solvolysis reactions of each of the compounds below with ethanol (6
pts).

Cl
Cl

5b.

Which of the two compounds below would react faster with ethanol? Explain your answer using
Hammond postulate and knowledge of ring strain. (7 pts).

5c.

Would such reactions proceed faster or slower upon addition of a less polar solvent, such as
hexane? Explain your answer using Hammond postulate. (7 pts).

Page 6
6a.

The following reaction produces a rearranged product. Also, the rate of the reaction is several
thousand times faster than the rate of nucleophilic substitution of 2-chlorobutane by the hydroxide
ion. Propose the mechanism of this reaction (10 pts).
Cl
N

NaOH
N

OH

6b
Using your knowledge of conformational analysis of acyclic molecules and presuming that methyl
group is sterically bulkier than a bromine atom, explain why the following E2 reaction produces a trans
alkene as a major product (10 pts).

Br

NaOMe
+
major

minor

Page 7
7.

Propose syntheses of each of the two compounds on the right starting from two reactants on the
left as the only source of carbon atoms. You can use any other inorganic reagents. Try to devise
the shortest syntheses in order to obtain maximum credit. (10 pts each).

and
H