A mechanism for the reaction of 1-chloroanthraquinone with methoxide ion to give the substitution product 1-methoxyanthraquinone is to be proposed using curved arrows to show the electron flow in each step. Concept introduction: Aryl halides that have electron-withdrawing groups undergo nucleophilic substitution reactions. The nucleophile first attacks the electron deficient aryl halide to form a resonance-stabilized, negatively charged intermediate, called Meisenheimer complex which then eliminates a halide ion to yield the product. To propose: Using curved arrows to show the electron flow in each step, a mechanism for the reaction of 1-chloroanthraquinone with methoxide ion to give the substitution product 1-methoxyanthraquinone.

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Aldol condensation- Synthesis of Dibenzalacetone reaction What is this reaction classified as?

Answer 1

Question

Chapter 16.SE, Problem 68AP

Interpretation Introduction

Interpretation:

A mechanism for the reaction of 1-chloroanthraquinone with methoxide ion to give the substitution product 1-methoxyanthraquinone is to be proposed using curved arrows to show the electron flow in each step.

Concept introduction:

Aryl halides that have electron-withdrawing groups undergo nucleophilic substitution reactions. The nucleophile first attacks the electron deficient aryl halide to form a resonance-stabilized, negatively charged intermediate, called Meisenheimer complex which then eliminates a halide ion to yield the product.

To propose:

Using curved arrows to show the electron flow in each step, a mechanism for the reaction of 1-chloroanthraquinone with methoxide ion to give the substitution product 1-methoxyanthraquinone.

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Aldol condensation- Synthesis of Dibenzalacetone reaction What is this reaction classified as?

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CH3 Ph3P-CHCH3 H3C H3C Aldehydes and ketones are converted into alkenes by means of a direct nucleophilic addition called the Wittig reaction. In the reaction, a triphenylphosphorine ylide, also called a phosphorane, adds to an aldehyde/ketone to give a four-membered cyclic intermediate called an oxaphosphetane. The oxaphosphetane is not isolated but instead spontaneously decomposes to release triphenylphosphine oxide and an alkene. Ph3P-CHCH3 H3C The ylide is formed by reaction of triphenylphosphine, a good nucleophile, with a primary alkyl halide in an S 2 reaction, followed by deprotonation of the carbon with a strong base, such as butyllithium. The carbonyl carbon and the carbon originally bonded to the halogen become the two carbons with the double bond in the product alkene :0: CH3 Com The real value of the Wittig reaction lies in its ability to yield an alkene of predictable structure, as the C-C bond is precisely where the C=O bond was in the reactant and no isomers (other than…