The compound expected to have the greatest and smallest heat of combustion is to be identified, and the reason for it is to be explained. Concept introduction: If the two molecules are isomers of each other, they have precisely the same combustion products. Therefore, any difference in the heat of combustion must be because of the differences in stabilities of the alkenes . The most stable compound has the smallest heat of combustion. Double bond stability increases as the amount of alkyl substitution increases due to hyperconjugation. The alkyl substitution is the number of alkyl groups bonded to the alkene carbon atoms.

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R₂ R₁ R₁ a R Rg Nu R₂ Rg R₁ R R₁₂ R3 R R Nu enolate forming R₁ R B-Alkylated carbonyl species or amines Cyclic B-Ketoester R₁₁ HOB R R₁B R R₁₂ B-Hydroxy carbonyl R diester R2 R3 R₁ RB OR R₂ 0 aB-Unsaturated carbonyl NaOR Aldol HOR reaction 1) LDA 2) R-X 3) H₂O/H₂O ketone, aldehyde 1) 2°-amine 2) acid chloride 3) H₂O'/H₂O 0 O R₁ R₁ R R₁ R₁₂ Alkylated a-carbon R₁ H.C R₁ H.C Alkylated methyl ketone acetoacetic ester B-Ketoester ester R₁ HO R₂ R B-Dicarbonyl HO Alkylated carboxylic acid malonic ester Write the reagents required to bring about each reaction next to the arrows shown. Next, record any regiochemistry or stereochemistry considerations relevant to the reaction. You should also record any key aspects of the mechanism, such as forma- tion of an important intermediate, as a helpful reminder. You may want to keep track of all reactions that make carbon-carbon bonds, because these help you build large molecules from smaller fragments. This especially applies to the reactions in…

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Chapter 5, Problem 5.54P

Interpretation Introduction

Interpretation:

The compound expected to have the greatest and smallest heat of combustion is to be identified, and the reason for it is to be explained.

Concept introduction:

If the two molecules are isomers of each other, they have precisely the same combustion products. Therefore, any difference in the heat of combustion must be because of the differences in stabilities of the alkenes. The most stable compound has the smallest heat of combustion. Double bond stability increases as the amount of alkyl substitution increases due to hyperconjugation. The alkyl substitution is the number of alkyl groups bonded to the alkene carbon atoms.

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