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Chapter 25: Q49P (page 1154)

If the following sesquiterpene is synthesized in a medium containing acetate with a 14C-labeled carbonyl carbon, which carbons will be labeled?

Short Answer

Expert verified

Carotenoids are tetraterpenes (40 carbons). Lycopene, the compound responsible for the red coloring of tomatoes and watermelon, and b-carotene, the compound that causes carrots and apricots to be orange, are carotenoids.

Step by step solution

01

Carotenoids

Carotenoids are tetraterpenes (40 carbons). Lycopene, the compound responsible for the red coloring of tomatoes and watermelon, and b-carotene, the compound that causes carrots and apricots to be orange, are carotenoids.

02

Identification of labelled carbon

The given sesquiterpene is produced from farnesyl pyrophosphate via cyclization followed by loss of a proton from the carbocation. Since, in farnesyl pyrophosphate C-2,C-4,C-6,C-8,C-10 and C-12 are labeled 14C carbons. Hence, labeled carbons in given sesquiterpene is as follows:

Structure of the desired product

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