14.35 How could you use Diels-Alder reactions to prepare the following products?Show the starting diene and dienophile in each case.(a)H(Ь)CN(c)(d)-CO2CH3HH 14.43 B-Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certainherbs. It has the molecular formula C10H16 and a UV absorption maximumat 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctaneis obtained. Ozonolysis of ß-ocimene, followed by treatment with zinc andacetic acid, produces the following four fragments:CH3CCH3HCHCH3C-CHHÖCH2CHAcetoneFormaldehydePyruvaldehydeMalonaldehyde(a) How many double bonds does ß-ocimene have?(b) Is B-ocimene conjugated or nonconjugated?(c) Propose a structure for B-ocimene.(d) Write the reactions, showing starting material and products.

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14.35 How could you use Diels-Alder reactions to prepare the following products? Show the starting diene and dienophile in each case. (a) H (b) CN (c) (d) .CO2CH3 H H

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Question

14.35 How could you use Diels-Alder reactions to prepare the following products?
Show the starting diene and dienophile in each case.
(a)
H
(Ь)
CN
(c)
(d)
-CO2CH3
H
H

14.43 B-Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain
herbs. It has the molecular formula C10H16 and a UV absorption maximum
at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane
is obtained. Ozonolysis of ß-ocimene, followed by treatment with zinc and
acetic acid, produces the following four fragments:
CH3CCH3
HCH
CH3C-CH
HÖCH2CH
Acetone
Formaldehyde
Pyruvaldehyde
Malonaldehyde
(a) How many double bonds does ß-ocimene have?
(b) Is B-ocimene conjugated or nonconjugated?
(c) Propose a structure for B-ocimene.
(d) Write the reactions, showing starting material and products.

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