Download QOI 0809 OH #2

QOI 0809 OH #2
Name___________________________________
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
1) Classify the reaction below as an oxidation, a reduction, or neither.
(CH3 )2CHCH2 OH → (CH3 )2CHCHO
A) oxidation
B) reduction
1)
C) neither
2) Classify the reaction below as an oxidation, a reduction, or neither.
PhCO2H → PhCH2 OH
A) oxidation
B) reduction
2)
C) neither
3) Classify the reaction below as an oxidation, a reduction, or neither.
cis-pent-2-ene → pentane
A) oxidation
B) reduction
3)
C) neither
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
4) Provide the structure of the major organic product in the reaction below.
4)
5) Provide the structure of the major organic product in the reaction below.
5)
6) Provide the structure of the major organic product in the reaction below.
6)
7) Provide the structure of the major organic product in the reaction below.
7)
(CH3 )3CCH2CH2 OH
Na2 Cr2 O7
→
H2 SO4
8) Provide the structure of the major organic product in the reaction below.
1
8)
9) Provide the structure of the major organic product in the reaction below.
9)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
10) In the chromic acid oxidation of alcohols, the chromium is:
A) oxidized from Cr+3 to Cr+6 .
B) oxidized from Cr+6 to Cr+3 .
C) reduced from Cr+3 to Cr+6 .
D) reduced from Cr+6 to Cr+3 .
E) none of the above
10)
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
11) Chromic acid oxidations are believed to proceed through a chromate ester intermediate. In
the oxidation of propran-1-ol, provide the structure of this ester and give the mechanism
for its conversion to the intermediate aldehyde.
11)
12) Provide the structure of the major organic product in the reaction below.
12)
(CH3 )2CHCH2 OH
Na
13) Provide the structure of the major organic product in the reaction below.
13)
14) Show the most efficient use of the Williamson ether synthesis to prepare
CH3 CH2CH2 OCH(CH3)2.
14)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
15) The Williamson ether synthesis proceeds via an __________ mechanism.
A) E1
B) SN1
C) SN2
D) E2
E) none of the above
15)
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
16) The enzyme, alcohol dehydrogenase, which is produced by the liver, converts ethanol to
__________, a normal body metabolite.
2
16)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
17) Poisonings by methanol and ethylene glycol are relatively common. How are these poisonings treated
clinically?
18) Provide the structure of the major organic product in the reaction below.
CH3 CH2CH(CH3 )CH2 CO2CH3
1. LiAlH4
→
2. H3 O+
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
19) Which of the following reagents can be used to convert cyclopentanol to cyclopentane?
A) TsCl, pyridine followed by LiAlH4
B) Na2 Cr2 O7, H2SO4
C) NaBH4 followed by H3 O+
19)
D) H2SO4, heat followed by H2, Pt
E) both A and D
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
20) Draw the tosylate ion and explain why it is a particularly good leaving group.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
21) Which of the following alcohols will give a positive chromic acid test?
A) tert-butanol
B) cyclohexanol
C) pentan-3-ol
D) both A and B
E) both B and C
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
22) Why are alcohols unreactive toward nucleophilic substitution reactions?
23) How can the electrophilicity of alcohols be increased? Suggest several specific ways.
24) Provide the structure of the major organic product in the reaction below.
PhCH2CH2 OH
1. TsC1, pyridine
→
2. NaCN, acetone
25) Provide the structure of the major organic product in the reaction below.
3
21)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
26) When (R)-butan-2-ol is treated with TsCl in pyridine, the product formed is:
A) an achial compound.
B) a single enantiomer.
C) a racemic mixture.
D) a mixture of diastereomers.
E) none of the above.
26)
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
27) Predict the major product of the reaction below and provide a stepwise mechanism which
accounts for its formation.
27)
(CH3 )3CCH2OH + HBr →
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
28) Predict the major product of the reaction below and provide a stepwise mechanism which accounts for its
formation.
CH3 (CH2)6 CH2 OH + HBr →
29) It is necessary to add ZnCl2 to promote the reaction of HCl with some alcohols while these same alcohols react
with HBr quite readily. Explain.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
30) Which of the following alcohols will react most rapidly with the Lucas reagent (HCl, ZnCl2 )?
A) CH3 CH2CH2 CH2 OH
B) (CH3 )3 COH
C) CH3 CH(OH)CH2 CH3
D) (CH3 )2 CHCH2 OH
30)
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
31) Provide the structure of the major organic product in the reaction below.
31)
32) Provide the structure of the major organic product in the reaction below.
32)
4
33) Provide the structure of the major organic product in the reaction below.
33)
34) Provide the structure of the major organic product in the reaction below.
34)
(CH3 )2CHCH2 OH
PBr3
35) Provide the structure of the major organic product in the reaction below.
PhCH2(OH)CH3
35)
SOCl2
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
36) Which set of reagents will best convert 2,2-dimethylpropan-1-ol (neopentyl alcohol) to
4,4-dimethylpentan-2-ol?
A) 1. SOCl2
B) 1. HCl, ZnCl2
C) 1. HCl, ZnCl2
D) 1. HCl
2. Mg
2. Mg
2. Mg
2. Mg
3. CH3 CHO
3. CH3 CHO
3. CH3 CHO
3. CH2O
4. H3O+
4. H3 O+
4. H3 O+
4. H3 O+
36)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
37) Which undergoes dehydration using concentrated H2 SO4 faster, cyclopentanol or 1-methylcyclopentanol?
Explain briefly.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
38) Which of the following alcohols undergoes dehydration upon heating with concentrated H2 SO4
without carbocation rearrangement?
A) 3-methylpentan-3-ol
B) 2-methyl-2-phenylpropan-1-ol
C) 3,3-dimethylpentan-2-ol
D) 2-methylhexan-3-ol
E) both A and B
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
39) Provide the structure of the major organic product in the reaction below.
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
40) What is Zaitsev's rule?
5
39)
38)
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
41) Provide the structure of the major organic product in the reaction below.
41)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
42) Dimethyl ether (CH3 OCH3) can be prepared by heating methanol in concentrated H2 SO4 . Provide a detailed,
stepwise mechanism for this process.
43) When an alcohol is heated in concentrated H2 SO4 , dehydration to produce both alkenes and ethers is possible.
Which process is more favored by higher reaction temperatures and why?
44) Provide a detailed, stepwise mechanism for the reaction below.
45) What alkene, which contains no oxygen atoms and a single CC, will give CH3 CO(CH2 )4CHO upon treatment
with OsO4 followed by cleavage with periodic acid?
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
46) The reaction of CH3 CH2 MgBr with CH3 COCH2 CH3 gives:
A) an achiral product.
B) the racemate of a chiral product.
C) a single enantiomer.
D) a mixture of diastereomers.
E) none of the above
46)
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
47) Draw the products formed in the Fischer esterification reaction between acetic acid
(CH3 CO2 H) and cyclohexanol.
47)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
48) Draw the structure of dimethyl sulfate, and provide a mechanism for the reaction of this compound with
sodium benzoate (PhCO2 Na).
49) Nitroglycerine is formed by the reaction of glycerine (propane-1,2,3-triol) and nitric acid. Provide the structure
of nitroglycerine.
50) What series of synthetic steps could be used to prepare 1-bromopentane from 1-bromopropane?
6
51) What series of synthetic steps could be used to prepare 1-methylcyclohexanol from cyclohexene?
52) What series of synthetic steps could be used to prepare hexan-3-ol from propan-1-ol?
53) What series of synthetic steps could be used to prepare (CH3 )2 CHCHO from (CH3)3 CH?
54) What series of synthetic steps could be used to prepare PhCH(OH)CH2 CH3 from PhCH2 OH?
55) What series of synthetic steps could be used to carry out the transformation shown below?
56) What series of synthetic steps could be used to carry out the transformation shown below?
57) What series of synthetic steps could be used to carry out the transformation shown below?
58) What series of synthetic steps could be used to carry out the transformation shown below?
59) What series of synthetic steps could be used to carry out the transformation shown below?
60) What series of synthetic steps could be used to carry out the transformation shown below?
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
61) Which of the following reagents is not typically viewed as an oxidizing agent?
A) Cl2
B) O2
C) KMnO 4
D) H2 O2
7
61)
E) KCl
62) Which of the following reagents is the best choice for oxidizing a primary alcohol to an aldehyde?
A) Na2 Cr2 O7, H2SO4
B) H2CrO4
C) KMnO 4
D) pyridinium chlorochromate
E) LiAlH4
62)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
63) Name the product which results when 1-methylcyclohexanol is treated with PCC.
64) Describe the composition of the Jones reagent.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
65) Which of the following catalysts is commonly used in industry to dehydrogenate alcohols?
A) CuO
B) NaBH4
C) (CH3 )2 S
D) Na
E) Zn
65)
66) What compound is produced when (R)-pentan-2-ol is treated with TsCl followed by NaI?
A) sodium (R)-pent-3-oxide
B) (S)-2-iodopentane
C) sodium (S)-pent-2-oxide
D) (R)-2-iodopentane
E) none of the above
66)
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
67) Provide the structure of the major organic product which results when ethyl tosylate is
reacted with potassium t-butoxide.
67)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
68) Through what basic mechanism is 1-methylcyclohexanol converted to
1-bromo-1-methylcyclohexane upon treatment with HBr?
A) SN2
B) E2
C) SN1
D) E1
E) radical chain
68)
69) What compound results when 1-butanol is treated with P/I2?
A) CH3 CH2CH2 CH2 I
B) CH3 CH2CH2 CH2 PI2
C) CH3 CH2CH2 CH2 OP(OH)2
D) racemic CH3 CH2CHICH3
E) Primary alcohols don't react with P/I2 .
69)
8
70) What class of organic compound is the major product of the acid catalyzed reaction of an alcohol
with a carboxylic acid?
A) nitrile
B) sulfonate ester
C) ester
D) thiol
E) ether
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
71) Provide the major organic product of the following reaction.
71)
72) Provide the major organic product of the following reaction.
72)
73) Provide the major organic product of the following reaction.
73)
74) Provide the major organic product of the following reaction.
74)
75) Provide the reagents necessary to carry out the multistep synthesis shown below.
75)
9
70)
76) Provide the major organic product of the following reaction.
76)
77) Provide the major organic product of the following reaction.
77)
78) Provide the major organic product of the following reaction.
78)
79) Provide the major organic product of the following reaction.
79)
80) What type of linkage bonds the individual nucleotides together in DNA?
80)
81) Provide the structure of the major organic product that results when 3-hexanol is treated
with sodium dichromate.
81)
82) Provide the structure of the major organic product that results when 1-octanol is treated
with pyridinium chlorochromate.
82)
83) Provide the name of the major organic product that results when cyclopentanol is
subjected to the following sequence of reactions: 1. TsCl, pyridine; 2. LiAlH4 .
83)
84) Provide the structure of the major organic product that results when 4-methyl-1-pentanol
is treated with PBr3 .
84)
85) Provide the name of the major organic product that results when
(R)-2-methyl-3-pentanol is heated with conc. H2 SO4 ..
85)
10
86) Provide the name of the major organic product that results when cyclopentanol is treated
with acetyl chloride.
86)
87) Provide the name of the major organic product that results when cyclopentanol is
subjected to the following sequence of reactions: 1. NaH; 2. CH3 CH2Br.
87)
88) Provide the name of the major organic product that results when
trans-4-methylcyclohexanol is treated with thinoyl chloride.
88)
89) Provide the name of the major organic product that results when
trans-4-methylcyclohexanol is treated with Lucas reagent.
89)
90) Provide the name of the major organic product that results when (R)-2-butyl tosylate is
treated with sodium iodide.
90)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
91) Which of the following compounds has carbon in the highest oxidation state?
A) CH3 CH2OH
B) CH3 C(OCH2 CH3 )3
C) CO2
91)
D) CH3 C(O)CH3
92) Which of the following oxidants will convert a primary alcohol to an aldehyde?
1) sodium dichromate /sulfuric acid
2) copper oxide
A) 2, 3, and 4
B) 1, 2, 3, and 4
C) 3
D) 3 and 4
E) none of the above
92)
3) pyridinium chlorochromate
4) dimethylsulfoxide, oxalyl chloride
93) Which alcohol reacts most rapidly with the Lucas reagent?
A) isobutanol
B) benzyl alcohol
C) methanol
93)
D) 2-propanol
94) Identify the sequence of reactions that successfully completes the following transformation.
A) 1) BH3
2) H2 O2 / NaOH
3) P, I2
B) HI / hν
C) 1) HBr / hν 2) NaI, acetone
D) A and C
E) all of the above
11
94)
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
95) With close attention to stereochemistry, provide the major organic product for the reaction
shown below.
95)
96) Provide the necessary reagents for the following conversion.
96)
97) Predict the outcome of the following reaction.
97)
98) What reagents are necessary for the following conversion?
98)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
99) Which energetic material is a nitrate ester?
A) TNT
B) nitroglycerin
99)
C) nitromethane
D) RDX
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
100) Predict the outcome of the following sequence of reactions.
12
100)
Answer Key
Testname: UNTITLED4
1) A
ID: oc6w 11-1
Diff: 1
2) B
ID: oc6w 11-2
Diff: 1
3) B
ID: oc6w 11-3
Diff: 1
4)
ID: oc6w 11-4
Diff: 2
5)
ID: oc6w 11-5
Diff: 2
6) No reaction. Tertiary alcohols are not oxidized by PCC.
ID: oc6w 11-6
Diff: 2
7) (CH3 )3CCH2CO2 H
ID: oc6w 11-7
Diff: 2
8)
ID: oc6w 11-8
Diff: 2
9)
ID: oc6w 11-9
Diff: 2
10) D
ID: oc6w 11-10
Diff: 1
13
Answer Key
Testname: UNTITLED4
11)
ID: oc6w 11-11
Diff: 2
12) (CH3 )2CHCH2 O- Na+
ID: oc6w 11-12
Diff: 2
13)
ID: oc6w 11-13
Diff: 1
14) (CH3 )2CHO- Na+ + CH3 CH2 CH2 Br
ID: oc6w 11-14
Diff: 2
15) C
ID: oc6w 11-15
Diff: 1
16) acetic acid
ID: oc6w 11-16
Diff: 2
17) The enzyme alcohol dehydrogenase converts these compounds to toxic substances in the body. If the patient receives
intravenous infusions of ethanol, then the ethanol swamps the enzyme and the potentially deadly alcohols pass from
the body unoxidized.
ID: oc6w 11-17
Diff: 3
18) CH3 CH2CH(CH3 )CH2 CH2 OH
ID: oc6w 11-18
Diff: 3
19) E
ID: oc6w 11-19
Diff: 2
20) Extensive resonance stabilization of this ion makes it a particularly good leaving group.
ID: oc6w 11-20
Diff: 2
21) E
ID: oc6w 11-21
Diff: 2
14
Answer Key
Testname: UNTITLED4
22) The hydroxide ion, a relatively strong base, is a very poor leaving group.
ID: oc6w 11-22
Diff: 2
23) The key is to convert the hydroxyl group into a better leaving group. Methods to do this include protonation,
conversion to the tosylate ester, and conversion to the halide.
ID: oc6w 11-23
Diff: 2
24) PhCH2CH2 CN
ID: oc6w 11-24
Diff: 2
25)
ID: oc6w 11-25
Diff: 2
26) B
ID: oc6w 11-26
Diff: 2
27)
ID: oc6w 11-27
Diff: 3
28)
ID: oc6w 11-28
Diff: 2
29) Cl- is a weaker nucleophile than is Br- . The Lewis acid ZnCl2 coordinates with the oxygen of the alcohol to increase its
electrophilicity and make it a better leaving group.
ID: oc6w 11-29
Diff: 2
30) B
ID: oc6w 11-30
Diff: 2
15
Answer Key
Testname: UNTITLED4
31)
ID: oc6w 11-31
Diff: 1
32)
ID: oc6w 11-32
Diff: 3
33)
ID: oc6w 11-33
Diff: 2
34) (CH3 )2CHCH2 Br
ID: oc6w 11-34
Diff: 2
35) PhCH2CHClCH3
ID: oc6w 11-35
Diff: 1
36) A
ID: oc6w 11-36
Diff: 2
37) 1-methylcyclopentanol; goes via the more stable 3° carbocation
ID: oc6w 11-37
Diff: 2
38) A
ID: oc6w 11-38
Diff: 2
39)
ID: oc6w 11-39
Diff: 1
40) When the product distribution of a series of isomeric alkenes is governed by their thermodynamic stabilities, the most
substituted isomer will predominate.
ID: oc6w 11-40
Diff: 2
41)
ID: oc6w 11-41
Diff: 2
16
Answer Key
Testname: UNTITLED4
42)
ID: oc6w 11-42
Diff: 2
43) Elimination to produce alkenes is favored by higher temperatures. The △S for this process is more positive than is the
case for the ether formation. This results in a more favorable -T△S term, making △G for the elimination reaction more
negative.
ID: oc6w 11-43
Diff: 3
44)
ID: oc6w 11-44
Diff: 3
45) 1-methylcyclohexene
ID: oc6w 11-45
Diff: 2
46) A
ID: oc6w 11-46
Diff: 2
47)
ID: oc6w 11-47
Diff: 2
17
Answer Key
Testname: UNTITLED4
48)
ID: oc6w 11-48
Diff: 3
49)
ID: oc6w 11-49
Diff: 1
50) 1. Mg, ether
2. ethylene oxide
3. HBr or PBr3
ID: oc6w 11-50
Diff: 2
51) 1. H2 O, H+ or BH3 ; H2 O2 , - OH or Hg(OAc)2, H2O; NaBH4
2. Na2 Cr2O7 , H+ or PCC or KMnO4
3. CH3 MgI
4. H3 O+
ID: oc6w 11-51
Diff: 3
52) 1. PCC
2. CH3 CH2 CH2MgBr
3. H3 O+
or
1. HBr or PBr3
2. Mg, Et2O
3. CH3 CH2 CHO
ID: oc6w 11-52
Diff: 2
53) 1. Br2 , hν
2. NaOEt, heat
3. BH3
4. H2 O2 , - OH
5. PCC
ID: oc6w 11-53
Diff: 3
54) 1. PCC
2. CH3 CH2 MgBr
3. H3 O+
ID: oc6w 11-54
Diff: 2
18
Answer Key
Testname: UNTITLED4
55) 1. PBr3 or HBr
2. Mg, ether
3. CH3 CH2 CHO
4. H3 O+
5. PCC or Na2 Cr2 O7 or KMnO4
ID: oc6w 11-55
Diff: 2
56) 1. Hg(OAc)2 , CH3CH2 OH
2. NaBH4
or
1. BH3
2. H2 O2 , - OH
3. Na
4. CH3 CH2 I
Note: The hydration in the second option could be accomplished with H+ , H2 O or Hg(OAc)2 , H2 O as well.
ID: oc6w 11-56
Diff: 2
57) 1. HBr, ROOR
2. NaCN
or
1. BH3
2. H2 O2 , - OH
3. HBr or PBr3
4. NaCN
ID: oc6w 11-57
Diff: 2
58) 1. BH3
2. H2 O2 , - OH
3. PCC
ID: oc6w 11-58
Diff: 1
59) 1. Cl2 , hν
2. NaOEt, heat
3. BH3
4. H2 O2 , - OH
5. PCC
6. CH3 MgBr
7. H2 SO4 , heat
ID: oc6w 11-59
Diff: 2
60) 1. HBr
2. Mg, Et2O
3. D2O
ID: oc6w 11-60
Diff: 2
19
Answer Key
Testname: UNTITLED4
61) E
ID: oc6w 11-61
Diff: 2
62) D
ID: oc6w 11-62
Diff: 2
63) No reaction occurs; Tertiary alcohols are resistant to mild oxidation conditions.
ID: oc6w 11-63
Diff: 2
64) Jones reagent is a dilute solution of chromic acid in acetone.
ID: oc6w 11-64
Diff: 2
65) A
ID: oc6w 11-65
Diff: 2
66) B
ID: oc6w 11-66
Diff: 2
67) CH3 CH2OC(CH3 )3
ID: oc6w 11-67
Diff: 2
68) C
ID: oc6w 11-68
Diff: 2
69) A
ID: oc6w 11-69
Diff: 1
70) C
ID: oc6w 11-70
Diff: 1
71)
ID: oc6w 11-71
Diff: 2
72)
ID: oc6w 11-72
Diff: 2
20
Answer Key
Testname: UNTITLED4
73)
ID: oc6w 11-73
Diff: 2
74)
ID: oc6w 11-74
Diff: 2
75) 1. H2SO4, Δ
2. BH3·THF
3. H2O2 , NaOH
4. PCC
ID: oc6w 11-75
Diff: 2
76)
ID: oc6w 11-76
Diff: 2
77)
ID: oc6w 11-77
Diff: 2
78)
ID: oc6w 11-78
Diff: 2
21
Answer Key
Testname: UNTITLED4
79)
ID: oc6w 11-79
Diff: 2
80) phosphate ester
ID: oc6w 11-80
Diff: 1
81) CH3 CH2COCH2 CH2 CH3
ID: oc6w 11-81
Diff: 2
82) CH3 (CH2)6 CHO
ID: oc6w 11-82
Diff: 2
83) cyclopentane
ID: oc6w 11-83
Diff: 2
84) (CH3 )2CHCH2 CH2 CH2 Br
ID: oc6w 11-84
Diff: 2
85) 2-methyl-2-pentene
ID: oc6w 11-85
Diff: 3
86) cyclopentyl acetate
ID: oc6w 11-86
Diff: 3
87) ethoxycyclopentane
ID: oc6w 11-87
Diff: 2
88) cis-1-chloro-4-methylcyclohexane
ID: oc6w 11-88
Diff: 2
89) a mixture of trans- and cis-1-chloro-4-methylcyclohexanes
ID: oc6w 11-89
Diff: 2
90) (S)-2-iodobutane
ID: oc6w 11-90
Diff: 2
91) C
ID: oc6w 11-91
Diff: 2
22
Answer Key
Testname: UNTITLED4
92) A
ID: oc6w 11-92
Diff: 3
93) B
ID: oc6w 11-93
Diff: 2
94) D
ID: oc6w 11-94
Diff: 3
95)
ID: oc6w 11-95
Diff: 2
96) 1) TsCl, pyridine
2) LiAlD4
ID: oc6w 11-96
Diff: 3
97)
ID: oc6w 11-97
Diff: 3
98) 1) Na2Cr2 O7 / H2 SO4
2) EtOH / acid catalyst
ID: oc6w 11-98
Diff: 3
99) B
ID: oc6w 11-99
Diff: 2
100)
ID: oc6w 11-100
Diff: 3
23