Chapter 21: 20P (page 817)
What starting materials are needed to prepare each alkene by a Wittig reaction? When there are two possible routes, indicate which route, if any, is preferred.
a.

b

c.

Short Answer
a.

b.

c.

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Chapter 21: 20P (page 817)
What starting materials are needed to prepare each alkene by a Wittig reaction? When there are two possible routes, indicate which route, if any, is preferred.
a.

b

c.

a.

b.

c.

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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.

Rank the following compounds in order of increasing reactivity towards nucleophilic attack.

What carbonyl compound and diol are needed to prepare each compound?
a.

b.

Draw a stepwise mechanism for the following reaction, a key step in the synthesis ofticlopidine, a drug that inhibits platelet aggregation. Ticlopidine has been used to reduce therisk of stroke in patients who cannot tolerate aspirin.
Safrole is a naturally occurring acetal isolated from sassafras plants. Once used as a common food additive in root beer and other beverages, it is now banned because it is carcinogenic. What compounds are formed when safrole is hydrolysed with aqueous acid?

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