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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: Like other electrophiles, carbocations add to alkenes to form new carbocations, which can then undergo substitution or elimination reactions depending on the reaction conditions. With this in mind, consider the following reactions of nerol, a natural product isolated from lemon grass and other plant sources. Treatment of nerol with TsOH forms α-terpineol as the major product, whereas treatment of nerol with chlorosulfonic acid, HSO₃Cl , forms a constitutional isomer, α-cyclogeraniol. Write stepwise mechanisms for both processes. Each mechanism involves the addition of an electrophile—a carbocation— to a double bond.

Question: Draw a stepwise mechanism for the following reaction.

Question: Draw the products of each reaction using the two-part strategy from Sample Problem 10.7.

Question: What alkene can be used to prepare each alkyl halide or dihalide as the exclusive or major product of an addition reaction?

a.

b.

c.

d.

Question: How many degrees of unsaturation are present in each compound?

$C_{6} H_{6}$
role="math" localid="1648637368534" $C_{8} H_{18}$
$C_{7} H_{8} O$
$C_{7} H_{11} B r$
$C_{5} H_{9} N$

See all solutions

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