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문제 32a,b,c
Draw the structures of the following compounds. (Includes both new and old names.)
(a) triphenylmethanol
(b) 4-(chloromethyl)heptan-3-ol
(c) 2-cyclohexen-1-ol
문제 32d,e
Draw the structures of the following compounds. (Includes both new and old names.)
(d) 3-cyclopentylhexan-3-ol
(e) meso-2,4-pentanediol
문제 32i,j
Draw the structures of the following compounds. (Includes both new and old names.)
i. cyclopent-3-ene-1-thiol
j. dimethyl disulfide
문제 32k
Draw the structures of the following compounds. (Includes both new and old names.)
(k) 3-methylhex-4-yn-2-ol
문제 33a,b
Predict which member of each pair has the higher boiling point, and explain the reasons for your predictions.
a. hexan-1-ol or 3,3-dimethylbutan-1-ol
b. hexan-2-one or hexan-2-ol
문제 34a
Predict which member of each pair is more acidic, and explain the reasons for your predictions.
a. cyclopentanol or 3-chlorophenol
문제 34b
Predict which member of each pair is more acidic, and explain the reasons for your predictions.
b. cyclohexanol or cyclohexanethiol
문제 35a
Predict which member of each group is most soluble in water, and explain the reasons for your predictions.
a. butan-1-ol, pentan-1-ol, or propan-2-ol
문제 35b
Predict which member of each group is most soluble in water, and explain the reasons for your predictions.
b. chlorocyclohexane, cyclohexanol, or cyclohexane-1,2-diol
문제 36a,b
Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).
(a)
(b)
문제 36c,d
Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).
(c)
(d)
문제 36f,g
Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).
(f)
(g)
문제 36j
Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).
(j)
문제 36k,l
Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).
(k)
(l)
문제 36m
Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).
(m)
문제 36n
Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).
(n)
문제 36p
Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).
(p)
문제 37a
Starting from bromobenzene and any other reagents and solvents you need, show how you would synthesize the following compounds. Any of these products may be used as starting materials in subsequent parts of this problem.
a. 1-phenylpropan-1-ol
문제 37b
Starting from bromobenzene and any other reagents and solvents you need, show how you would synthesize the following compounds. Any of these products may be used as starting materials in subsequent parts of this problem.
b. 1-phenylpropene
문제 37c
Starting from bromobenzene and any other reagents and solvents you need, show how you would synthesize the following compounds. Any of these products may be used as starting materials in subsequent parts of this problem.
c. 1-phenylpropan-2-ol
문제 37d
Starting from bromobenzene and any other reagents and solvents you need, show how you would synthesize the following compounds. Any of these products may be used as starting materials in subsequent parts of this problem.
d. 3-phenylprop-2-en-1-ol
문제 38
Write structures for a homologous series of alcohols (R―OH) having from one to six carbons.
문제 38a
Show how you would synthesize the following alcohol from appropriate alkene.
(a)
문제 38b
Show how you would synthesize the following alcohol from appropriate alkene.
(b)
문제 38d
Show how you would synthesize the following alcohol from appropriate alkene.
(d)
문제 39a
Show how you would use Grignard syntheses to prepare the following alcohol from the indicated starting material and any other necessary reagents.
(a) octan-3-ol from hexanal, CH3(CH2)4CHO
문제 39d
Show how you would use Grignard syntheses to prepare the following alcohol from the indicated starting material and any other necessary reagents.
(d) 2-cyclohexylethanol from bromocyclohexane
문제 39e
Show how you would use Grignard syntheses to prepare the following alcohol from the indicated starting material and any other necessary reagents.
(e) benzyl alcohol (Ph–CH2–OH) from bromobenzene (Ph–Br)
문제 39g
Show how you would use Grignard syntheses to prepare the following alcohol from the indicated starting material and any other necessary reagents.
(g) cyclopentylphenylmethanol from benzaldehyde (Ph–CHO)
문제 40b
Show how you would accomplish the following transformations. You may use any additional reagents you need.
(b)
