2. (a) Reaction of an alkene with ozone followed by an oxidative workup gives the product shown. What is the structure of alkene A? A (b) Compounds B and C both have the formula C10H16. Hydrogenation of either compound over Pt gives the same product, cis-1-isopropyl-4-methylcyclohexane. Ozonolysis with reductive workup fragments the two compounds differently, as shown below. What are the structures of B and C? (CHCl3, chloroform, is the solvent.) C B 1) 03, CHCI 3 2) (CH3)2S 1) 03, CHCI3 2) (CH3)2S H O 1) 03 2) H₂O₂, H₂O O H CH3 + + H- HO₂C H Do

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2. (a) Reaction of an alkene with ozone followed by an
oxidative workup gives the product shown. What is the
structure of alkene A?
A
(b) Compounds B and C both have the
formula C10H16. Hydrogenation of either
compound over Pt gives the same product,
cis-1-isopropyl-4-methylcyclohexane.
Ozonolysis with reductive workup
fragments the two compounds differently,
as shown below. What are the structures of C
B and C? (CHCl3, chloroform, is the
solvent.)
B
1) 03, CHCI 3
2) (CH3)2S
1) 03, CHC13
2) (CH3)2S
H
O
1) 03
2) H₂O2, H₂O
H3C-
H
O
CH3
3. (a) Draw the structures of all enols that would spontaneously form this ketone,
including stereoisomers.
+
+
I
HO₂C
H
+
La
CH3CH₂-C-CH(CH3)2
O=
(b) Would alkyne hydration be a good preparative method for this compound? If so, give the reaction. If not,
explain why.
Transcribed Image Text:2. (a) Reaction of an alkene with ozone followed by an oxidative workup gives the product shown. What is the structure of alkene A? A (b) Compounds B and C both have the formula C10H16. Hydrogenation of either compound over Pt gives the same product, cis-1-isopropyl-4-methylcyclohexane. Ozonolysis with reductive workup fragments the two compounds differently, as shown below. What are the structures of C B and C? (CHCl3, chloroform, is the solvent.) B 1) 03, CHCI 3 2) (CH3)2S 1) 03, CHC13 2) (CH3)2S H O 1) 03 2) H₂O2, H₂O H3C- H O CH3 3. (a) Draw the structures of all enols that would spontaneously form this ketone, including stereoisomers. + + I HO₂C H + La CH3CH₂-C-CH(CH3)2 O= (b) Would alkyne hydration be a good preparative method for this compound? If so, give the reaction. If not, explain why.
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