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Chapter 16: PROBLEM 16.8 (page 612)

Question. Draw all possible resonance structures for the following cation and indicate which structure makes the largest contribution to the resonance hybrid.

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01

Resonance Structure

The group of Lewis contributing structures that represents all possible bond and charge shifts in a compound is known as the resonance structures.

The compound has a 鈥榯hree allyl system鈥�, so that pi-electrons shift forming a new carbocation in which there is an electronegative atom with a lone pair of electrons.

The lone pair shifts forming a resonance structure with more number of bonds and less charge separation.

Possible resonance structures of the given cation

02

Major Contributor of Hybrid

The resonance structure that best resembles the resonance hybrids in terms of bonds and charges separation is known as the major contributor of resonance hybrid.

The main contributor of resonance of the given cation is the one with the highest number of bonds and least charge separation

The major contributor of resonance

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Most popular questions from this chapter

Question: Rank the following compounds in order of increasing stability.

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b.

c.

Question: Compounds containing triple bonds are also Diels鈥揂lder dienophiles. With this in mind, draw the products of each reaction.

a.

b.

Question: Diels鈥揂lder reaction of a monosubstituteddiene (such as CH2=CH-CH=CHOCH3) with a monosubstituteddienophile (such as CH2=CHCHO) gives a mixture of products, but the 1,2-disubstituted product often predominates. Draw the resonance hybrid for each reactant and use the charge distribution of the hybrids to explain why the 1,2-disubstituted product is the major product.

Question: Draw the products of each reaction. Indicate the stereochemistry of Diels鈥揂lder products.

a.

b.

c.

d.

Question: Label each product in the following reaction as a 1,2-product or 1,4-product, and decide which is the kinetic product and which is the thermodynamic product.
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