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Chapter 21: 17P (page 817)

Draw the products of the following Wittig reactions

a.

b.

Short Answer

Expert verified

a.

b.

Step by step solution

01

Wittig reaction 

The treatment of a carbonyl compound with triphenylphosphonium ylide forms an alkene. Tiphenylphosphonium ylide is known as the Wittig reagent.

02

Product formation

a.

The reaction of propan-2-one with Ph3P=CH2 is shown below:

Product formation in a

b.

The reaction of cyclopentanone with Ph3P=CHCH2 CH2 CH2 CH3is shown below:

Product formation in b

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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

Show two different methods to carry out the following transformation: a one-step method using a Wittig reagent, and a two-step method using a Grignard reagent. Which route, if any, is preferred?

What carbonyl compound and alcohol are formed by hydrolysis of each acetal?

a.

b.

c.

Give the IUPAC name for each ketone

a.

b

c

Although the carbonyl absorption of cyclic ketones generally shifts to higher wavenumber with decreasing ring size, C=O of cyclopropenone absorbs at lower wavenumber in its roman IR spectrum than the C=O of cyclohex-2-enone. Explain this observation by using the principles of aromaticity learned in Chapter 17.
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