Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 23, Problem 25P
Interpretation Introduction

Interpretation:

The mechanism thataccounts for each step of the given synthesis is to be written.

Concept introduction:

Cyperone derives its name from the Cyperusrotundus, a nut grass found in tropical, subtropical and temperate regions. It can exist in both αand β forms. It is majorly used in the medication of androgen-, estrogen-, and progestin-related hormonal diseases. Its molecular formula is C15H22O. Chemically, it is a terpene.

Robinson annulation process is an effective process for the ring formation of six-membered polycyclic compounds, such as lipids and steroids. It works with three important steps, which are as follows: conjugate addition of resonance-stabilized carbanion, aldol condensation, and elimination of hydroxyl ion (OH).

Aldol condensation involves the addition of the aldol (aldehyde and alcohol) group, followed by condensation of the product. In this reaction, the enolate of an aldehyde or a ketone reacts at the αcarbon with the carbonyl part of the other molecule to produce an βhydroxy aldehyde or a ketone.

Michael addition is a reaction that involves the conjugate addition of a resonance-stabilized carbanion for the formation of an enolate.

The reaction thatinvolves the removal of an αproton through a base is known as E1 elimination reaction.

The reaction thatinvolves the removal of the OH group through dehydration is known as E2 elimination reaction.

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The following substances can be prepared by a nucleophilic addition reaction between an aldehyde or ketoneand a nucleophile. Identify the reactants from which they were prepared. If the substance is an acetal, identifythe carbonyl compound and the alcohol; if it is an imine or enamine, identify the carbonyl compound and theamine. You do not have to consider stereochemistry. In cases where there is more than one answer, just giveone. Use Grignard reagents when an organometallic reagent is required. Draw the Grignard reagent as acovalent magnesium bromide.
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…
The ketone shown was prepared in a three-step sequence from ethyl trifluoroacetate. The first step in the sequence involved treating ethyl trifluoroacetate with ammonia to give compound A. Compound A was in turn converted to the desired ketone by way of compound B. Fill in the missing reagents in the sequence shown, and give the structures of compounds A and B.
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