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문제 31b
Like other strong nucleophiles, triphenylphosphine attacks and opens epoxides. The initial product (a betaine) quickly cyclizes to an oxaphosphetane that collapses to an alkene and triphenylphosphine oxide.
(b) Show how this sequence might be used to convert cis-cyclooctene to trans-cyclooctene.
문제 32
(a) Outline the syntheses indicated in Solved Problem 18-2, beginning with aldehydes and alkyl halides.
(b) Both of these syntheses of 1-phenylbuta-1,3-diene form the central double bond. Show how you would synthesize this target molecule by forming the terminal double bond.
문제 33a,b
Show how Wittig reactions might be used to synthesize the following compounds. In each case, start with an alkyl halide and a ketone or an aldehyde.
(a) Ph–CH=C(CH3)2
(b) Ph–C(CH3)=CH2
문제 33c,d
Show how Wittig reactions might be used to synthesize the following compounds. In each case, start with an alkyl halide and a ketone or an aldehyde.
(c) Ph–CH=CH–CH=CH–Ph
(d)
문제 34a
Predict the major products of the following reactions.
(a)
문제 34b
Predict the major products of the following reactions.
(b)
문제 34c
Predict the major products of the following reactions.
(c)
문제 34d
Predict the major products of the following reactions.
(d)
문제 35a
Propose a mechanism for both parts of the Wolff–Kishner reduction of cyclohexanone: the formation of the hydrazone, and then the base-catalyzed reduction with evolution of nitrogen gas.
문제 35b
Propose a mechanism for both parts of the Wolff–Kishner reduction of cyclohexanone: the formation of the hydrazone, and then the base-catalyzed reduction with evolution of nitrogen gas.
문제 36a
Predict the major products of the following reactions:
(a)
문제 36b
Predict the major products of the following reactions:
(b)
문제 36c
Predict the major products of the following reactions:
(c)
문제 36d
Predict the major products of the following reactions:
(d)
문제 37a
Draw structures of the following derivatives.
(a) the 2,4-dinitrophenylhydrazone of benzaldehyde
문제 37b
Draw structures of the following derivatives.
(b) the semicarbazone of cyclobutanone
문제 37c
Draw structures of the following derivatives.
(c) cyclopropanone oxime
문제 37d
Draw structures of the following derivatives.
(d) the ethylene acetal of hexan-3-one
문제 37e
Draw structures of the following derivatives.
(e) acetaldehyde dimethyl acetal
문제 37f
Draw structures of the following derivatives.
(f) the methyl hemiacetal of formaldehyde
문제 37g
Draw structures of the following derivatives.
(g) the (E) isomer of the ethyl imine of propiophenone
문제 37h
Draw structures of the following derivatives.
(h) the hemiacetal form of 5-hydroxypentanal
문제 38b
Name the following ketones and aldehydes. When possible, give both a common name and an IUPAC name.
(b) CH3(CH2)2CO(CH2)2CH3
문제 38c
Name the following ketones and aldehydes. When possible, give both a common name and an IUPAC name.
(c) CH3(CH2)5CHO
문제 38d
Name the following ketones and aldehydes. When possible, give both a common name and an IUPAC name.
(d) PhCOPh
문제 38g
Name the following ketones and aldehydes. When possible, give both a common name and an IUPAC name.
(g) CH3CH2CHBrCH2CH(CH3)CHO
문제 38h
Name the following ketones and aldehydes. When possible, give both a common name and an IUPAC name.
(h) Ph–CH=CH–CHO
문제 38j
Name the following ketones and aldehydes. When possible, give both a common name and an IUPAC name.
(j)
문제 38k
Name the following ketones and aldehydes. When possible, give both a common name and an IUPAC name.
(k)
문제 38l
Name the following ketones and aldehydes. When possible, give both a common name and an IUPAC name.
(l)
