From the given compounds, the four β − hydroxy aldehyde formed by crossed aldol reaction are to be predicted. Concept introduction: Electrophiles are electron deficient species that has positive or partially positive charge. Lewis acids are electrophiles that accept electron pair. Nucleophiles are electron-rich species that has negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair. Free radical is an atom, molecule, or ion that has an unpaired electron, which makes it highly chemically reactive. Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction. Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction. Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules. A carbon-carbon bond formation occurs by aldol addition and aldol condensation reaction. Aldol reaction is preferred in basic conditions over acidic conditions as after the aldol condensation, acid catalysis promotes the reaction further. An aldol reaction takes place by acid catalysis, and direct dehydration of β − hydroxy aldol intermediate forms α , β − unsaturated product. A chemical reaction that is catalyzed by an acid is called acid catalyzed reaction. A chemical reaction that is catalyzed by a base is called base catalyzed reaction. An aldol reaction takes place in a protic solvent with a base. Dehydration of aldol addition product leads to the formation of conjugated α , β − unsaturated carbonyl compound and the overall reaction is aldol condensation. A reaction between two different carbonyl compounds known as a crossed aldol reaction. A crossed aldol reaction forms mixture of products by pairing different carbonyl reactants.

Question

Draw the friedel-crafts acylation mechanism of m-Xylene

Answer 1

Question

Chapter 19, Problem 34P

Interpretation Introduction

Interpretation:

From the given compounds, the four β− hydroxy aldehyde formed by crossed aldol reaction are to be predicted.

Concept introduction:

Electrophiles are electron deficient species that has positive or partially positive charge. Lewis acids are electrophiles that accept electron pair.

Nucleophiles are electron-rich species that has negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair.

Free radical is an atom, molecule, or ion that has an unpaired electron, which makes it highly chemically reactive.

Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.

Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.

Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.

A carbon-carbon bond formation occurs by aldol addition and aldol condensation reaction.

Aldol reaction is preferred in basic conditions over acidic conditions as after the aldol condensation, acid catalysis promotes the reaction further.

An aldol reaction takes place by acid catalysis, and direct dehydration of β− hydroxy aldol intermediate forms α,β− unsaturated product.

A chemical reaction that is catalyzed by an acid is called acid catalyzed reaction.

A chemical reaction that is catalyzed by a base is called base catalyzed reaction.

An aldol reaction takes place in a protic solvent with a base.

Dehydration of aldol addition product leads to the formation of conjugated α,β− unsaturated carbonyl compound and the overall reaction is aldol condensation.

A reaction between two different carbonyl compounds known as a crossed aldol reaction.

A crossed aldol reaction forms mixture of products by pairing different carbonyl reactants.

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Draw the friedel-crafts acylation mechanism of m-Xylene

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1. Base on this experimental results, how do you know that the product which you are turning in is methyl 3-nitrobenzoate(meta substituted product ) rather than either of the other two products? 2. What observation suggests that at least a small amount of one or both of the other two isomers are in the mother liquor?