DEPARTMENT OF CHEMISTRY AND CHEMICAL TECHNOLOGY
ORGANIC CHEMISTRY II
202-BZG-05 03
TEST 2
8 APRIL 2010
INSTRUCTOR: I. DIONNE
PRINT YOUR NAME: _____________________________________________
INSTRUCTIONS:
Answer all questions in the space provided.
1.
2.
3.
4.
5.
6.
7.
Duration of the exam is 75 minutes.
Answer all questions in the space provided.
Answer the questions in ink in order to preserve the right to grieve.
In order to obtain full credit for your answers, you must clearly show your work.
Calculators may not be shared. Programmable calculators are not permitted.
No books or extra paper are permitted.
Your attention is drawn to the College policy on cheating. This policy will be enforced.
PROBLEM 1
(8 marks)
Provide names or structural formulas for the following compounds:
(a)
(b)
(c)
OH
O
OH
(d)
(e)
CH2OCH3
SH
(f)
O
(g)
(h)
2,2,7-trimethyl-3,5-octanediol
4-chloro-3-methylphenol
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PROBLEM 2
(12 marks)
Identify the choice that best completes the statement or answers the question.
(a) Which of the following compounds is most soluble in water?
1. CH3CH2CH2CH2CH3
2. CH3OCH2CH3
3. CH3CH2CH2OH
4. CH3CH2CH2CH2CH2OH
Answer:_____
(b) The boiling point of diethyl ether is nearly the same as that of
1. dimethyl ether
2. butyl alcohol
3. 1-pentanol
4. pentane
Answer:_____
(c) What is the hybridization of the oxygen atom in alcohols?
1. sp
2. sp2
3. sp3
4. sp3d
Answer:_____
(d) When phenol dissolves in water, it functions as
1. a weak base
2. a weak acid
3. an oxidizing agent
4. a reducing agent
Answer:_____
(e) What alcohol is known as wood alcohol?
1. ethylene glycol
2. 2-propanol
3. methanol
4. ethanol
Answer:_____
(f) Which of the following is the strongest acid?
1.
2.
OH
OH
F
F
F
F
(g) Which of these is a reducing agent?
1. CrO3/H+
2. KMnO4
3. LiAlH4
4. HCOOOH
Answer:_____
Answer:_____
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(h) Refer to the data below:
1.
2.
3.
4.
5.
pKa
9.89
8.28
7.17
9.65
10.21
Y
-H
m-NO2
p-NO2
m-OCH3
p-OCH3
Y
OH
The weakest acid in the table is ___________________
Answer:_____
Which of the acids in the table has the weakest conjugate base?
Answer:_____
(i) Which method(s) would work to quantitatively prepare a sodium ethoxide
solution?
i. CH3CH2OH + NaOH
ii CH3CH2OH + NaH
iii CH3CH2OH + Na
1.
2.
3.
4.
i and ii
i and iii
ii and iii
i, ii, and iii
Answer:_____
(j) The reaction shown below can be described as an
OH
CH3CHCH2Br
NaOH, H2O
O
CH3CH CH2
1. acid-base reaction followed by an intramolecular Williamson ether
synthesis
2. acid-base reaction followed by an intramolecular S N1 reaction
3. E2 reaction followed by an addition reaction to a double bond
4. SN2 reaction followed by an intramolecular Williamson ether synthesis
Answer:_____
(k) Which of the following mechanistically depicts the protonation of
tert-butyl alcohol by hydrogen bromide?
1.
3.
2.
4.
Answer:_____
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PROBLEM 3
(6 marks)
Over each arrow show the reagent(s) and any other necessary reactants for the following
reactions
(a)
O
OH
H
OH
Cl
(b)
(c)
OH
(d)
O
OH
OH
(e)
O
H3C
H
(f)
H
CH3
O
OH
OH
PROBLEM 4
(10 marks)
Provide the organic product(s) of the following reactions. If no reaction occurs, write "NR."
(a)
conc HI (excess)
+
CH3OCH2CH3
reflux
(b)
NaOCH3
O
H2C CH CH3
(c)
O
CH3OH
1. LiAlD4
2. H2O
(d)
CH3CH2MgBr
CH3CH2OH
CH3CH2OH
PBr3
+
(e)
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(f)
LiAlH4
CH3CH2OH
(g)
H3C
(h)
PhSNa
Br
OH
CH3
CrO3
aq. H2SO4
PROBLEM 5
(4 marks)
Show the two reagents needed to prepare the following ethers using the Williamson
synthesis.
(a) CH3CH2CH2 O CH(CH3)2
(b)
CH2 O CH2CH3
Page | 6
PROBLEM 6
(4 marks)
Show what Grignard reagent and what carbonyl compound you would start with to prepare
the alcohol shown below. Provide one route.
(a)
OH
CH3CCH2CH3
CH3
(b)
OH
CCH2CH2CH3
CH3
PROBLEM 7
(4 marks)
Show the complete mechanism for the reaction below.
H3C
O
+
HBr
Page | 7
PROBLEM 8
(6 marks)
When the epoxide shown below was treated with sodium methoxide in methanol, a new
compound X was obtained. The spectral data for X are given below. Propose a structure for X
and a mechanism for its formation. Show your reasoning.
Cl C(CH3)3
O
CH3O
X
CH3OH
MS: m/z (relative intensity in parenthesis): 130 (4), 85 (12), 57 (100), 45 (31)
1
H NMR (δ ppm): 1.17 (singlet, 9H), 3.42 (singlet, 3H), 4.29 (singlet, 2H)
IR: strong signal at 1720 cm–1
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4
5
6
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