Download Organic Chemistry I-2 Ans Chapter 7 Free Radical Answers 1

Organic Chemistry I-2 Ans
Chapter 7 Free Radical Answers
1. Please write down the major product of the following reactions:
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Organic Chemistry I-2 Ans
2. Please write down the major product of the following reactions:
3. Please write down the major product of the following reactions:
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Organic Chemistry I-2 Ans
4. Give the major product of the reaction of 1-methylcyclohexene with the following reagents:
a. NBS//CH2Cl2
b. Br2/ CH2Cl2
c. HBr
d. HBr/peroxide
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Organic Chemistry I-2 Ans
Chapter 8 Alkylhalides SN Answers
1. Name the following alkyl halides according to IUPAC rules:
(a) 3,4-dibromo-2,6-dimethylheptane
(b) 5-iodo-2-hexene
(c) 2-bromo-5-chloro-2,6-dimethyl-heptane
3-bromomethylhexane
2. Draw structures corresponding to the following IUPAC names:
Cl
Cl
(a) 2,3-Dichloro-4-methylhexane
I
Br
(b) 4-Bromo-4-ethyl-2-methylhexane
3. Give the major product of the following reactions:
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(c) 3-Iodo-2,2,4,4-tetramethylpentane
Organic Chemistry I-2 Ans
4. What nucleophiles could be used to react with butyl bromide to prepare the following compounds?
a. HOB. CH3CH2SH C. CH3OH D. CH3NH2
E. CN- F. NaSH
5. Which one in each of the following pairs will react faster in an SN2 reaction with OH-?
a. CH3I (better leaving group) b. dimethyl sulfoxide will not stabilize the nucleophile by hydrogen bond
c. CH3Cl (less steric hindrance) d. H2C=CHBr (vinylic can not undergo SN2)
6. What products would you expect from the reaction of 1-bromopropane with each of the following?
a. CH3CH2CH2NH2
b. CH3CH2CH2OC(CH3)3
c. CH3CH2CH2I
d CH3CH2CH2OH
e. CH3CH2CH2SH
7. Rank the following sets of compounds with respect to SN2 reaction.
8. Rank the following sets of compounds with respect to SN1 reaction.
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Organic Chemistry I-2 Ans
9. Which reaction in each of the following pairs will take place more rapidly?
10. Which of the following alkyl halides form a substituted product from an SN1 reaction that is different
from the substituted product formed from an SN2 reaction?
d. no difference
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Organic Chemistry I-2 Ans
11. Draw the products obtained from the solvolysis of each of the following compounds in ethanol:
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Organic Chemistry I-2 Ans
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Organic Chemistry I-2 Ans
Chapter 9 Elimination Ans
1. Give the major elimination product obtained from an E2 reaction of each of the following alkyl halides
with hydroxide ion (HO-):
2. Which alkyl halide would you expect to be more reactive in an E2 reaction:
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Organic Chemistry I-2 Ans
3. For each of the following reactions, draw the major elimination product; if the product can exist as
stereoisomers, indicate which stereoisomer is obtained in greater yield.
4. Give the major elimination product obtained from an E1 reaction of each of the following alkyl halides
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Organic Chemistry I-2 Ans
5. What alkene will be formed in an E2 reaction of each of the following compounds?
a. (1S, 2S)-1-bromo-1,2-diphenylpropane
b. (1S,2R)-1-bromo-1,2-diphenylpropan
6. How do you make the product with the starting material?
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Organic Chemistry I-2 Ans
7. How do you make the product with the starting material?
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Organic Chemistry I-2 Ans
Chapter 10 alcohols Ans
1.
Give the major product of each of the following reactions:
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Organic Chemistry I-2 Ans
2. Give the structure of W, X, Y, Z (NB. Pay attention to the stereochemistry).
3. Find the major product formed when each of the following alcohols is heated in the presence of H2SO4:
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Organic Chemistry I-2 Ans
4. Draw the chemical structure of the product from the following reactions:
a.
b,
c.
e. CH3CH2CH2CH2CH2CN
d.
f.
CH3CH2CH2CH2CH2O
G.
CH3CH2CH2CH=CH2
MINOR
+
CH3CH2CH=CHCH3
MAJOR
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H.
CH3CH2CH2CH2CH2Cl
Organic Chemistry I-2 Ans
I
J
CH3
CH3CH2CH2OH
CH3CHCH2CH2CH2OH
k.
L.
N.
O.
M.
P
5. Predict the product(s) of the following transformations:
O
H
Br
HOCH3CHCH2CH3
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+
CH3I
Organic Chemistry I-2 Ans
6. Show how you could prepare the following substances from cyclohexanol:
O
KMnO4
Br
PBr3
OH
H2SO4
(1) H2SO4
(2) H2, Pd
7. Show how you could prepare the following substances from 1-propanol:
PCC
CH3CH2CHO
KMnO4/ H+
CH3CH2CO2H
CH3CH2CH2OH
SO2Cl
CH3CH2CH2Cl
Na metal
CH3CH2CH2ONa
8. How would you prepare the following ethers?
(a)
OH
Na
ONa
OCH2CH3
CH3CH2Br
(b)
H3C
H
H3C Br
H
H
OHCH3
Br2
H
CH3
H2O
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H3C
O
H
Na
H
CH3
Organic Chemistry I-2 Ans
9.What are the reagents a-d in the following reactions?
A. H2SO4
or
H3PO4
B) CH3CO3H C. (1) Na,
(2) CH3Br
d. H+/H2O
10. Using the given starting material, any inorganic reagents, and any carbon-containing compounds with
no more than 2 carbon atoms, indicate how the following syntheses could be carried out:
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Organic Chemistry I-2 Ans
11. How the following compounds could be prepared using ethylene oxide as one of the reactants:
a. CH3CH2CH2CH2OH
B. CH3CH2CH2CH2Br C. CH3CH2CH2CH3
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Organic Chemistry I-2 Ans
Chapter 11 & 12 Answers
1. Which of the following compounds are aromatic?
Ans. (only show the aromatic compounds)
Cycloheptatrienyl cation
Cyclononatetraenyl anion
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Organic Chemistry I-2 Ans
2. Provide the necessary reagents next to the arrows.
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Organic Chemistry I-2 Ans
3. Draw the structure of each of the following compounds:
(a) m-chlorotoluene (b) p-bromophenol (c) o-nitroaniline (d) m-chlorobenzonitrile
(e) 2-bromo-4-iodophenol (f) m-dichlorobenzene (g) 2,5-dinitrobenzaldehyde (h) o-xylene
(i) m-ethylphenol (j) p-nitrobenzenesulfonic acid (k) (E)-2-phenyl-2-pentene
o-bromoaniline (m). 2,4-dichlorotoluene (n) (E)-2-phenyl-2-pentene
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Organic Chemistry I-2 Ans
4. Draw the product of each of the following reactions:
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Organic Chemistry I-2 Ans
Chapter 13 Answers
Draw the structure of the major product(s) of mononitration of the following substances:
propylbenzene (b) bromobenzene (c) benzaldehyde (d) benzoic acid
(e) cyclohexylbenzene (f) benzonitrile (g) nitrobenzene (h) phenol
A.
B.
CH2CH2CH3
CH2CH2CH3
Br
+
+
NO2
O2N
C.O N
2
O2N
CHO
Br
d
O2N
NO2
E
CO2H
+
O2N
NO2
f
g
O2N
O2N
OH
H
NO2
CN
OH
+
O2N
NO2
4. Draw the structure of the major product(s) of electrophilic monochlorination of the following
substances:
O2 N
OH
O2 N
OH
(a) m-nitrophenol,
Cl
Cl
When one substituent has a pair of non-bonding electrons available for adjacent charge stabilization, it will
normally exert the product determining influence
(b) o-methylphenol,
Cl
OH
Cl
OH
CH3
CH3
(c) p-chloronitrobenzene
O2N
Cl
Cl
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Organic Chemistry I-2 Ans
5. Draw the structure of the major product(s) of sulfonation of the following substances:
(a) o-chlorotoluene
SO3H
Cl
Cl
HO3S
CH3
CH3
(b) m-bromophenol
SO3H
HO3S
HO
Br
HO
Br
(c) p-nitrotoluene
O2N
SO3H
CH3
6. Give the product of the reaction of excess benzene with each of the following reagents:
a. isobutyl chloride + AlCl3
b. neopentyl chloride + AlCl3
c. propene + HF
d. dichloromethane + AlCl3
6. Give the products of the following reactions:
a.
O
OCCH3
+ HNO3
O
O
OCCH3
OCCH3
H2SO4
+
O2N
NO2
b.
O
OCH3
1. AlCl3
+
OCH3
OCH3
O
O
+
O
OH
2. H2O
O
O
HO
O
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Organic Chemistry I-2 Ans
c.
CH3
CH2Br
d.
CH2MgBr
O
OH
Mg
NBS/∆
CH3
CH3
CH3
D2O
Mg
Br
D
MgBr
Br
e.
+ Br2
N
CF3
f.
+
N
Cl
Br
CF3
Cl2
FeCl3
g
O
O
CCH2CH2CH2Cl
1. AlCl3
2. H2O
O
h.
CH2CH2CCl
1. AlCl3
2. H2O
O
CH3
i.
CHCH3
CO2H
NaCrO7, H
+
∆
j.
CH2CH3
1. AlCl3
NO REACTION
2. H2O
CH3
k.
CH3
CH2Br
NBS
CH2OCH3
CH3ONa
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N
Organic Chemistry I-2 Ans
7. Show how the following compounds can be prepared from benzene:
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Organic Chemistry I-2 Ans
j
k.
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Organic Chemistry I-2 Ans
L
M
N
O
P
Q
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Organic Chemistry I-2 Ans
8. For each of the following compounds, indicate the ring carbon that would be nitrated if the compound
was treated with HNO3/H2SO4:
H
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