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Chapter 21: 35P (page 817)

How would you use a protecting group to carry out the following transformation?

Short Answer

Expert verified

Any chemical compound used in the modification of the reacting compound in order to specify the site of chemo-selectivity is known as the ‘protecting groups.’

Acetals are used as the protecting group of carbonyl compounds.

Step by step solution

01

Protecting group

Any chemical compound used in the modification of the reacting compound in order to specify the site of chemo-selectivity is known as the ‘protecting groups.’

Acetals are used as the protecting group of carbonyl compounds.

02

Acetal group

The given compound has two reactive functional groups among which ketone is more reactive than the ester group.

Therefore, the carbonyl group is converted into an acetal group as follows,

Mechanism

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Most popular questions from this chapter

(a) Explain how in can reduce hemiacetal A to butane-1,4-diol (b) What product is formed when A is treated with ? (c) The drug isotretinoin is formed by the reaction of X and Y. What is the structure of isotretinoin? Although isotretinoin (trade name Accutane or Roaccutane) is used for the treatment of severe acne, it is dispensed under strict controls because it also causes birth defects

What lactol (cyclic hemiacetal) is formed from intramolecular cyclization of each hydroxy aldehyde?

a.

b.

Use the 1 H NMR and IR data to determine the structure of each compound.

What reagents are needed to convert each compound into butanal (CH3CH2CH2CHO )?

a.

b.

c.

Draw the structure of all constitutional isomers that contain a ketone and have molecular formula C5H10O. Give the IUPAC name for each isomer and state how NMR spectroscopy could be used to distinguish these isomers.
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