Solution Found!
When compound Z is treated with ozone, followed by
Chapter 21, Problem 39SP(choose chapter or problem)
When compound Z is treated with ozone, followed by dimethyl sulfide and washing with water, the products are formic acid, 3-oxobutanoic acid, and hexanal.
Propose a structure for compound Z. What uncertainty is there in the structure you have proposed?
Equation Transcription:
Text Transcription:
O_{3}
(CH_{3})_{2}S, H_{2}O
H-C-OH
CH_{3}-C-CH_{2}-C-OH
CH_{3}(CH_{2})_{4}-C-H
Questions & Answers
QUESTION:
When compound Z is treated with ozone, followed by dimethyl sulfide and washing with water, the products are formic acid, 3-oxobutanoic acid, and hexanal.
Propose a structure for compound Z. What uncertainty is there in the structure you have proposed?
Equation Transcription:
Text Transcription:
O_{3}
(CH_{3})_{2}S, H_{2}O
H-C-OH
CH_{3}-C-CH_{2}-C-OH
CH_{3}(CH_{2})_{4}-C-H
ANSWER:
Solution 39SP
Step 1
Ozonolysis:
Ozonolysis of an alkene, followed by hydrolysis, cleaves the double bond and gives ketone and aldehydes.
Ozonolysis of an alkyne, followed by hydrolysis, cleaves the triple bond and gives two carboxylic acids.
4-Methyl-4-decen-1-yne (Z) is reacted with ozone, followed by dimethyl sulfide and washing with water, the products are formic acid, 3-oxobutanoic acid, and hexanal.
