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Chapter 10: PROBLEM 10.68 (page 424)

Question: Alkene A can be isomerized to isocomene, a natural product isolated from goldenrod, by treatment with TsOH. Draw a stepwise mechanism for this conversion. (Hint: Look for a carbocation rearrangement.)

Short Answer

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Answer

Step by step solution

01

Isomerization of alkene

The isomerization alkene occurs by the formation of a carbocation intermediate.

This intermediate carbocation leads to 1,2-bond shift (driving force is the relaxation of the strained molecule), which forms another isomer of the alkene.

02

Explanation

The given alkene compound is acidified by TsOH to form a tertiary carbocation intermediate. Further, the 1,2-bond shift occurs from the highly strained four-membered ring to give another alkene isomer.

Isomerization of the alkene

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Most popular questions from this chapter

Question: Draw the six alkenes of the molecular formula C5H10. Label one pair of diastereomers.

Question: What alkylborane is formed from hydroboration of each alkene?

Question: Draw the products formed when (CH3)2C=CH2 is treated with each reagent.

a. HBr

b.H2O, H2SO4

c. CH3CH2HO,H2SO4

d. Cl2

e.Br2 ,H2O

f. NBS (aqueous DMSO)

g. [1] BH3; [2] H2O2 ,HO-

Question: Draw the constitutional isomer formed when the following alkenes are treated with each set of reagents: [1] H2O,H2SO4; or [2] BH3followed by H2O2,HO-.

Question: Linolenic acid (Table 10.2) and stearidonic acid are omega-3 fatty acids, unsaturated fatty acids that contain the first double bond located at C3, when numbering begins at the methyl end of the chain. Predict how the melting point of stearidonic acid compares with the melting points of linolenic and stearic acids. A current avenue of research is examining the use of soybean oil enriched in stearidonic acid as a healthier alternative to vegetable oils that contain fewer degrees of unsaturation.
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