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Chapter 18: Q57P (page 971)

Both NaBH4 and NaBD4 are commercially available, and D2O is common and inexpensive. Show how you would synthesize the following labelled compounds, starting with propanone.

Short Answer

Expert verified

Sodium borohydride (NaBH4) or sodium borodeuteride (NaBD4) is used as a reducing agent which reduces aldehyde or ketone to its corresponding alcohol.

Step by step solution

01

Introduction

Sodium borohydride (NaBH4) or sodium borodeuteride (NaBD4) is used as a reducing agent which reduces aldehyde or ketone to its corresponding alcohol.

02

Reduction of ketone with NaBH4 or NaBD4  in presence of H2O or  D2O

Ketones on treatment with NaBD4 followed by hydrolysis with H20 yields a product in which the carbonyl group is reduced to hydroxyl group . Also, ketones on treatment with NaBD4 followed by hydrolysis with D20 yields a product in which the carbonyl group is reduced to hydroxyl group where D atom is present in place of H atom.

03

Synthesis of the given compounds from propanone (a ketone)

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Most popular questions from this chapter

Question: The family of macrolide antibiotics all have large rings (macrocycle) in which an ester is what makes the ring; a cyclic ester is termed as a lactone. One example is amphotericin B, used as an anti-fungal treatment of last resort because of its liver and heart toxicity. Professor Martin Burke of the University of Illnois has been making analogs to retain the antifungal properties but without the toxicity, including this structure published in 2015. (Nature Chemical Biology, (2015) doi: 10.1038/nchembio.1821). The carboxylate of amphotericin B has been replaced with the urea group (shown in red).

(a) Where is the lactone group that forms the ring?

(b) Two groups are circled. What type of functional group are they? Explain.

Give the structures of the carbonyl compound and the amine used to form the following imines.

(a)

(b)

(c)

(d)

(e)

(f)

Why were no products from McLafferty rearrangement observed in the spectrum of butan-2-one?

Question. An unknown compound gives a molecular ion of m/z 70 in the mass spectrum. It reacts with semicarbazide hydrochloride to give a crystalline derivative, but it gives a negative Tollens test. The NMR and IR spectra follow. Propose a structure for this compound, and give peak assignments to account for the absorptions in spectra. Explain why the signal atin the IR spectrum appears at an unusual frequency.

Show how you would accomplish the following syntheses.

(a).benzene鈫�n - butylbenzene

(b).benzonitrile鈫�propiophenone

(c).benzene鈫�p - methoxybenzaldehyde

(d).Ph(CH2)4-OH鈫�tetralone
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