The different experimental conditions used to give the major and minor product distribution should be given. Concept Introduction: Carbonyl compound when treated with LDA (Lithium Diisopropylamide) undergoes deprotonation at the α -carbon to form enolate. The enolate formed is resonance stabilized as the negative charge will be spread over other atoms too. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance. Deprotonation of α carbon to form enolate Nucleophilic attack of enolate S N 2 reaction with alkyl halide Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer. Asymmetric center is a sterocenters which arises to hydrocarbons if the carbon is bonded to four different groups. Chiral carbon: Chiral carbon is the one which is bonded to four different molecules or groups.

Question

A task is assigned to an undergraduate student to test two samples (known as compounds K and L) in the laboratory. She placed these two compounds through various scientific tests. She discovered that these compounds have the same molecular formula, CSHSO. When treated with 2,4-dinitrophenylhydrazine, all of these compounds produce brightly coloured precipitate, and both are reduced to an organic compound with the molecular formula C§H100. However, compound K can be easily oxidized by chromic acid to formed compound N and vice versa for compound L. Furthermore, when both compounds react with Fehling's solutions, they produce negative results. However, only compound K forms a silver mirror when it reacts with Tollen's reagent, and compound L does not. Identify the possible structural formulae for compounds K, L, and N by ignoring their position isomerism. Indicate the formation of compound N from compound K. Predict the chemical reaction that occurs when compound L reacts with 2,4-…

Answer 1

Question

Chapter 19, Problem 19.51P

Interpretation Introduction

Interpretation:

The different experimental conditions used to give the major and minor product distribution should be given.

Concept Introduction:

Carbonyl compound when treated with LDA (Lithium Diisopropylamide) undergoes deprotonation at the α-carbon to form enolate. The enolate formed is resonance stabilized as the negative charge will be spread over other atoms too. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance.

Deprotonation of α carbon to form enolate

Nucleophilic attack of enolate

S_N2 reaction with alkyl halide

Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.

Asymmetric center is a sterocenters which arises to hydrocarbons if the carbon is bonded to four different groups.

Chiral carbon: Chiral carbon is the one which is bonded to four different molecules or groups.

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