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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 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 all stereoisomers formed in each reaction.

Question: Devise a synthesis of each compound from the indicated starting material.

Question: Draw the products, including stereochemistry, of each reaction. 

Question: Draw a stepwise mechanism that shows how all three alcohols are formed from the bicyclic alkene.
See all solutions

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