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Oxidative cleavages can help to determine the positions of
Chapter 21, Problem 24P(choose chapter or problem)
Oxidative cleavages can help to determine the positions of the triple bonds in alkynes.
(a) An unknown alkyne undergoes oxidative cleavage to give adipic acid and two equiva-
lents of acetic acid. Propose a structure for the alkyne.
(b) An unknown alkyne undergoes oxidative cleavage to give the following triacid plus one
equivalent of propionic acid. Propose a structure for the alkyne.
Equation Transcription:
Text Transcription:
O_3
H_{2}O
HOOC-(CH_{2})_{3}-COOH+2CH_{3}COOH
O_3
H_{2}O
COOH
HOOC-(CH_{2})_{7}-CH-COOH+CH_{3}CH_{2}COOH
Questions & Answers
QUESTION:
Oxidative cleavages can help to determine the positions of the triple bonds in alkynes.
(a) An unknown alkyne undergoes oxidative cleavage to give adipic acid and two equiva-
lents of acetic acid. Propose a structure for the alkyne.
(b) An unknown alkyne undergoes oxidative cleavage to give the following triacid plus one
equivalent of propionic acid. Propose a structure for the alkyne.
Equation Transcription:
Text Transcription:
O_3
H_{2}O
HOOC-(CH_{2})_{3}-COOH+2CH_{3}COOH
O_3
H_{2}O
COOH
HOOC-(CH_{2})_{7}-CH-COOH+CH_{3}CH_{2}COOH
ANSWER:
Answer :(a)
)