Concept explainers
Interpretation:
The use of cyclic acetal in carrying out the given conversion is to be shown and the reason why the direct addition of methyl magnesium bromide fails to carry out the conversion is to be explained.
Concept introduction:
Electrophiles are electron deficient species, which has positive or partially positive charge. Lewis acids are electrophiles, which accept electron pair.
Nucleophiles are electron rich species, which has negative or partially negative charge. Lewis bases are nucleophiles, which donate electron pair.
Nucleophilic addition reaction is an addition reaction where electron deficient or electrophilic double or triple bond reacts with electron rich species (nucleophile), with disappearance of the double bond and creation of two single bonds.
When same compound contains two moieties with carbonyl groups, both are reactive toward nucleophilic addition. The more reactive one undergoes the reaction faster. The more reactive group has to be protected to make the less reactive one undergoes a reaction.
The protection can be done by converting ketone to cyclic acetals, because of which only ester group is available.
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EBK ORGANIC CHEMISTRY
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- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning