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Chapter 10: PROBLEM 10.66 (page 424)

Question: Explain why A is a stable compound but B is not.

Short Answer

Expert verified

Answer

Due to the maximum overlapping of orbitals in compound A.

Step by step solution

01

Norbornene

Norbornene is an organic compound with a cyclohexane ring. Its positions 1 and 4 have a methylene bridge. Therefore, the molecule is highly strained and unstable.

02

Stability of norbornene

The stability of norbornene depends on the overlapping of the orbitals of the double bond and the methylene carbon.

03

Explanation

Compound A shows maximum overlapping of the orbitals of the alkene with methylene carbon. The overlapping gives more stability to norbornene.

Compound B has a double bond perpendicular to the bridged methylene carbon. Therefore, the overlapping of orbitals is minimum in this case, and the compound is unstable.

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Most popular questions from this chapter

Question: Draw a stepwise mechanism for the following reaction. This reaction combines two processes together: the opening of an epoxide ring with a nucleophile and the addition of an electrophile to a carbon鈥揷arbon double bond. (Hint: Begin the mechanism by protonating the epoxide ring.)

Question: Calculate the number of degrees of unsaturation for each molecular formula.

a. C6H8

b. C40H56

c. C10H16O2

d. C8H9Br

e. C8H9ClO

f. C7H11N

g. C4H8BrN

h. C10H10ClNO

Question: Treatment of 3-methylcyclohexene with HCl yields two products, 1-chloro-3-methylcyclohexane and 1-chloro-1-methylcyclohexane. Draw a mechanism to explain this result.

Question: Iejimalide B, an anticancer agent with a 24-membered ring, is isolated from a tunicate found off Ie Island in Okinawa.

(a) Label each double bond in iejimalide B as Eor Z.

(b) Label each tetrahedral stereogenic center as Ror S.

(c) How many stereoisomers are possible for iejimalide B?

Question: What three alkenes (excluding stereoisomers) can be used to prepare 3-chloro-3-methylhexane by addition of HCl?
See all solutions

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