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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: Give the structure corresponding to each name.

a. (E)-4-ethylhept-3-ene

b. 3,3-dimethylcyclopentene

c. 4-vinylcyclopentene

d. (Z)-3-isopropylhept-2-ene

e. cis-3,4-dimethylcyclopentene

f. 1-isopropyl-4-propylcyclohexene

g. 3,4-dimethylcyclohex-2-enol

h. 3,5-diethylhex-5-en-3-ol

Question: Bromoetherification, the addition of the elements of Br and OR to a double bond, is a common method for constructing rings containing oxygen atoms. This reaction has been used in the synthesis of the polyether antibiotic monensin (Problem 21.37). Draw a stepwise mechanism for the following intramolecular bromoetherification reaction.

Question: Give the IUPAC name for each alkene.

Question: Label each carbon-carbon double bond in 11-cis-retinal as E or Z. As we will learn in Section 21.11, the isomerization of one double bond in this compound to a less crowded stereoisomer takes place when light strikes the retina of the eye.

Question: Which alkene reacts faster with HBr? Explain your choice
See all solutions

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