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Chapter 11: Q60P (page 590)

The Williamson ether synthesis involves the displacement of an alkyl halide or tosylate by an alkoxide ion. Would the synthesis shown be possible by making a tosylate and displacing it? If so, show the sequence of reactions. If not, explain why not and show an alternative synthesis that would be more likely to work.

Short Answer

Expert verified

The compound derived from tosyl chloride is tosylate.This compound is an ionic species and is represented by the symbol ‘Ts’. It is useful for organic synthesis for SN2 reactions.

Step by step solution

01

About tosylate

The compound derived from tosyl chloride is tosylate.This compound is an ionic species and is represented by the symbol ‘Ts’. It is useful for organic synthesis for SN2 reactions.

02

About the reaction

The given reaction cannot proceed via SN2 reactions because there is a possibility of a backside attack due to the blockage of bridgehead carbon by the other bridgehead.

Another reason is the impossibility of bridgehead carbon to undergo inversion due to the constraints of the bridged ring system.

03

About the chemical reaction

The sketch of the chemical reaction is given below.

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Most popular questions from this chapter

The following pseudo-syntheses (guaranteed not to work) exemplify a common conceptual error.

(a)What is the conceptual error implicit in these syntheses?

(b)Propose syntheses that are more likely to succeed.

To practice working through the early parts of a multistep synthesis, devise syntheses of

(a) pentan-3-one from alcohols containing no more than three carbon atoms.

(b) 3-ethylpentan-2-one from compounds containing no more than three carbon atoms.

Some alcohols undergo rearrangement or other unwanted side reactions when they dehydrate in acid. Alcohols may be dehydrated under mildly basic conditions using phosphorus oxy-chloride (POCl3) in pyridine. The alcohol reacts with phosphorus oxychlorides much like it reacts with tosyl chloride (Section 11-5), displacing a chloride ion from phosphorus to give an alkyl dichlorophosphate ester. The dichlorophosphate group is an outstanding leaving group. Pyridine reacts as a base with the dichlorophosphate ester to give an E2 elimination. Propose a mechanism for the dehydration of cyclohexanol by POCl3 in pyridine.

Unlike ethylene glycol, propylene glycol (propane-1, 2-diol) is non toxic because it oxidizes to a common metabolic intermediate. Give the structures of the biological oxidation products of propylene glycol.

Show how you would use a simple chemical test to distinguish between the following pairs of compounds. Tell what you would observe with each compound.

(a)isopropyl alcohol andtert-butyl alcohol

(b)isopropyl alcohol and butan-2-one, CH3COCH2CH3

(c)hexan-1-ol and cyclohexanol

(d)allyl alcohol and propan-1-ol

(e)butan-2-one andtert-butyl alcohol
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