Sample Problems for Exam
CHEM 2425 EXAM # 2 ( Chapters 17-20)
Directions- Please bubble your correct answer in scantron
1. Which of the following would you expect to have the highest boiling point?
A. isopropyl alcohol B. t-butyl alcohol
C. diethyl ether
D. n-butanol
2. Which of the following would be the highly miscible with (most soluble in) water?
A. CH3- CH2 – CH2 – CH2OH
B. CH3 – CH(OH) – CH2- CH3
C. CH3 – C(CH3)2 – CH2OH
D. CH3 – C(CH3)2 (OH)
3. What is the product of refluxing methylethyl ether with HI in acidic solution?
A. ethanol and methyl iodide
C. ethanol and methyl alcohol
B. methanol and ethyl iodide
D. iodoethane and methanol
4. Which of the following is (bromomethyl)ethyl ether?
A. CH3CH2 – O – CH2Br
C. CH3 – O - CH2 -CH2- Br
B. CH3 – O –CH2Br
D. CH3CH2 – O- CH2CH2Br
5. 2-Methoxypentane is classified as ______________________ .
A. a symmetrical ether
B. a secondary alcohol
C. an epoxide
D. an ether
6. The following reaction classifies as __________________ .
R-CHO
 R- CH2OH
A. an oxidation
B. a reduction
C. hydration
7. What is the correct name for the following compound ?
O
H3C
A. 1,2-dimethyloxide
C. 1,2- Dimethylepoxide
C
H
C
H
CH3
B. 2,3-epoxy butane
D. all of these
D. tautomerization
8. Which reagent(s) would accomplish the following reaction ?
SO3H
OH
A. H2O, H+
B. NaOH/H3O+
C. LiAlH4
D. CH3MgBr/H2O
9. Which of the following reagent(s) provides the following conversion.
CH - CH3
CHO
OH
A. CH3COOH/H+
B. MnO4– / H2O, heat
C. CH3COCl /AlCl3
D. none of these
10. What is the product of the following reaction?
OH
PCC
A.
O
CHO
COOH
D.
C.
B.
11. Which of the following is called an acyl group?
A. R-COO-
B. R-CO-
C. R-CO-O-CO-
D. C = O
12. Which of the following used as a suffix of carbaldehyde in naming?
A.
CHO
CHO
CHO
B.
C.
D. all of these
13. Aryl ketones are prepared by the following reaction. This reaction is called_________________.
CO - CH3
AlCl3 / heat
+ CH3-CO Cl
A. Friedel-Crafts Alkylation
C. Wolff-Kishner reaction
B. Friedel-Crafts Acylation
D. Hofmann reaarangement
14. Which of the following is an example of an enamine?
A. R2 C =NR
C. R2 C = C R –NR2
B. R2 NH
D. R4 N+
15. Aldehydes and ketones are reduced by NaBH4 or LiAlH4 to yield ___________ and _________
alcohols.
A. 10 and 20
B. 20 and 10
C. 10 and 30
D. 20 and 30
16. Which of the following has higher boiling point?
A. CH3 COOH
B. CH3 CH2 COOH
C. HCOOH
D. C6H5COOH
17. Which of the following is most acidic?
A. FCH2 COOH
B. ClCH2COOH
C. F3C COOH
D. CH3CH2 COOH
18. Which of the following reagents used for the following conversion?
NO2
NO2
CH3
COOH
A. KMnO4, H2O, heat
B. LiAlH4, THF /H3O+
C.
CrO3 /H3O+
D. BH3, THF /H3O+
PART II - Nomenclature
a) Write the correct IUPAC names.
OH
OCH3
O
OH
CH2-CH3
OH
(A)
(B)
(C)
OCH3
(D)
(E)
COOH
O
CH3 - CH2- CH - CH2 -CN
CH3
(F)
CH3
OH
(G)
(H)
A. ____________________________
B. _____________________________
C. ____________________________
D. _____________________________
E.________________________________ F_________________________________
G________________________________
H________________________________
b) Write the correct structures .
1.tert-butylalcohol
2. 3-isopropyl-1-hexanol
3. ethylmethyldisulfide
………………………………
4. 3,4-dimethyl-1-pentanol
6. 2-phenylcyclopentanone
………………………………
7. 1,4- butanedioic acid
5. 2-methyltetrahydrofuran
8. 3-methylhexanal
PARTT III- REACTIONS
What major product(s) would you expect from the following reactions?
a)
Cl
Na NH2 / NH3
b)
KMnO4/H2O/heat
c)
OH
SOCl2/pyridine
CH3
d)
CO-CH3
NaBH4/ether
H3O+
NO2
e)
1) RCO3H/CH2Cl2
1) CH3CH2MgBr/ether
f)
CH3-CH2- CHO
2) H2O
g)
O
OsO4/peroxide
NaHSO3/H2O
h)
CH3 - CH2 - CH2OH
PCC
CH2Cl2
2) H3O
i)
O
C
Cl + (CH3CH2)2 CuLi
j)
O
NH3
CH3 - CH2 - C - Cl
k)
COOH
1) LiAlH4 or BH3
2) H3O
l)
O
CH3 - CH - CH2 - C - H
CrO3 / H3O
CH3
m)
OH
O
C
Cl + CH3- CH - CH3
n)
Br
Na CN
THF
o)
CH3
CH3 - CH2 - CH - C
O
OH
SOCl2
CHCl3
p)
O
C - O - CH3
1) DIBAH, toluene
2) H3O
q)
O
1. (Ph)3P + (CH3)2CHBr
2. BuLi/THF
ether
PART IV – SYNTHESIS
a) What is the best procedure for preparing the following compound from benzene?
( requires more than one step)
OCH3
b) Identify the structures for the compounds A, C, D, E and F.
CH3
Compound (A) + CH3Cl/AlCl3
CH3CH2OH
KMnO4
(C)
water/heat
acid
(D)
hydrolysis
(E) + (F)
c) Illustrate the mechanism for acid catalyzed dehydration of 1-methylcyclohexanol. Be sure to use
curved arrows (electron flow) for complete credit.
d)
COOH
OH
CH - CH3
e)
CHEM 2425 EXAM # 2 ( Chapters 17-20) – Answers
Part I: Multiple Choice
1. D
6. B
2. D
7. B
3. A
8. C
4. A
9. D
5. D
10. D
11. B
12. A
13. B
14. C
15. A
Part II: Nomenclature
a) A. 3,3-dimethylpentanol
D. m-dimethoxybenzene
G. 3-methylpentanenitrile
b)
16. D
17.C
18.A
B. benzyl alcohol
C. 3-ethyl-1,2-epoxycylopentane
E. 2-ethyl-3-methylphenol
F.2-meethylcyclohexanone
H. m-hydroxybenzoic acid
CH3
CH3
C
OH
OH
CH3CH2
CH3
1. tert-butylalcohol
2. 3-isopropyl-1-hexanol
O
S
S
CH3
3. ethylmethyldisulfide
CH3
OH
4. 3,4-dimethyl-1-pentanol 5. 2-methyltetrahydrofuran
O
OH
HO
O
O
6. 2-phenylcyclopentanone 7.1,4-butanedioic acid
O
H
8. 3-methylhexanal
Part III: Reactions
Cl
NH2
a)
COOH
b)
CHOH - CH3
c)
d)
NO2
COOH
CH3
e)
f)
O
and
g)
OH
CH3CH2
CH
CH2CH3
OH
OH
O
h) CH3CH2 C - H
m)
CO - O - CH - CH3
CH3
CO - CH2 - CH3
i)
n)
CN
j) CH3 - CH2 - CO - NH2
CH2OH
o)
k)
CH3 - CH2 - CH - CO Cl
CH3
l) CH3 - CH - CH2 - COOH
p)
CHO
CH3
q)
OH
OH
Part IV: Synthesis
a)
OCH3
Br
1) NaH
2) CH3Cl, ether
/AlBr3
OH
NBS/CCl4
1) Hg(OAc)2,H2O
2) NaBH4
Br
KOH
ethanol
b)
O
C
COOH
D.
C.
A.
OCH2CH3
CH2OH
E.
F. CH3 CH2 OH
c)
CH3
CH3
..
OH
..
H - HSO4
..
O-H
H
oxonium ion formation
protonation
dehydration
CH3
CH3
HSO4
tertiary carbocation
+ H2SO4
H
Methyl cyclohexene
e)
d)
OH
COOH
CH - CH3
BH3, THF
H2O2, OH
LiAlH4 / H3O
OH
PBr3
CN
Br
CH3COCl
AlCl3
/ H3O
CN
NaBH4 /ethanol/ H3O
or
PCC /CH2Cl2
CO - CH3