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Organic Chemistry I-2 Ans 1 Chapter 7 Free Radical Answers 1. Please write down the major product of the following reactions:
Organic Chemistry I-2 Ans
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Chapter 7 Free Radical Answers 1. Please write down the major product of the following reactions:
Organic Chemistry I-2 Ans
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2. Please write down the major product of the following reactions: 3. Please write down the major product of the following reactions:
Organic Chemistry I-2 Ans
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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
Organic Chemistry I-2 Ans
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(c) 3-Iodo-2,2,4,4-tetramethylpentane
Cl
Cl
(a) 2,3-Dichloro-4-methylhexane
Br
(b) 4-Bromo-4-ethyl-2-methylhexane
I
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: 3. Give the major product of the following reactions:
Organic Chemistry I-2 Ans
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4. What nucleophiles could be used to react with butyl bromide to prepare the following compounds? a. HO- B. 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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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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11. Draw the products obtained from the solvolysis of each of the following compounds in ethanol:
Organic Chemistry I-2 Ans
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12
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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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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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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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7. How do you make the product with the starting material?
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Chapter 10 alcohols Ans 1. Give the major product of each of the following reactions:
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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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4. Draw the chemical structure of the product from the following reactions: a. b, c. d. e. CH3CH2CH2CH2CH2CN f. G. H. CH3CH2CH2CH2CH2Cl
CH3CH2CH2CH2CH2O
MINOR
CH3CH2CH2CH=CH2 CH3CH2CH=CHCH3+
MAJOR
Organic Chemistry I-2 Ans
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CH3CH2CH2OH
CH3CHCH2CH2CH2OH
CH3
CH3I+
I J k. L. M. N. O. P 5. Predict the product(s) of the following transformations:
H
O
HOCH3CHCH2CH3
Br
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PCC
CH3CH2CH2OHSO2Cl
CH3CH2CHO
CH3CH2CO2H
CH3CH2CH2Cl
CH3CH2CH2ONa
KMnO4/ H+
Na metal
6. Show how you could prepare the following substances from cyclohexanol: 7. Show how you could prepare the following substances from 1-propanol: 8. How would you prepare the following ethers? (a) (b)
KMnO4
OH
H2SO4
PBr3Br
O
(1) H2SO4
(2) H2, Pd
OHNa
ONaCH3CH2Br
OCH2CH3
H
H3C H
CH3
Br2
H2OH
H3C H
CH3
Br
OH
Na
H
H3C H
CH3
O
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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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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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Cycloheptatrienyl cationCyclononatetraenyl anion
Chapter 11 & 12 Answers 1. Which of the following compounds are aromatic? Ans. (only show the aromatic compounds)
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2. Provide the necessary reagents next to the arrows.
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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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4. Draw the product of each of the following reactions:
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CHOO2N
CNO2NNO2O2N
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 C. d f g 4. Draw the structure of the major product(s) of electrophilic monochlorination of the following substances: (a) m-nitrophenol, 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, (c) p-chloronitrobenzene
OHO2N
Cl
OHO2N
Cl
OH
CH3
OH
CH3Cl
Cl
ClO2N
Cl
CH2CH2CH3
O2N
CH2CH2CH3
NO2
+
A.Br
O2N
Br
NO2
+
B.
CO2HO2N
O2NNO2
+
E
OH
O2N
OH
NO2
+
H
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OCCH3
O
H2SO4OCCH3
O
NO2
OCCH3
O
O2N
+ HNO3 +
OCH3
O
O
O
OCH3
O
OH
OOCH3
O
HO
O+
1. AlCl3
2. H2O
+
5. Draw the structure of the major product(s) of sulfonation of the following substances: (a) o-chlorotoluene (b) m-bromophenol (c) p-nitrotoluene 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. b.
Cl
CH3HO3S
Cl
CH3
SO3H
BrHO
HO3S SO3H
BrHO
CH3
O2N SO3H
Organic Chemistry I-2 Ans
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CH2CH3
CH3
1. AlCl3
2. H2O
CH3 CH2BrMg
CH2MgBr OOHNBS/∆
+N + Br2 N
Br
NBr
CF3
FeCl3
CF3Cl Cl2
CCH2CH2CH2Cl
O
1. AlCl3
2. H2O
O
CH2CH2CCl
O
O
1. AlCl3
2. H2O
CHCH3
CH3
CO2HNaCrO7, H+
∆
CH3 CH2BrCH3ONa
CH2OCH3
NBS
c. d. e. f. g h. i. j. NO REACTION k.
Br
CH3
Mg
MgBr
CH3
D2O
D
CH3
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7. Show how the following compounds can be prepared from benzene:
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j k.
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L M N O P Q
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8. For each of the following compounds, indicate the ring carbon that would be nitrated if the compound was treated with HNO3/H2SO4: H
