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Chapter 18: Q64P (page 971)

Hydration of alkynes (via oxymercuration) gives good yields of single compounds only with symmetrical or asymmetrical alkynes. Show what products would be from hydration fo each compound.

(a) hex-3-yne

(b) hex-2-yne

(c) hex-1-yne

(d) cyclodecyne

(e) 3-methylcyclodecyne

Short Answer

Expert verified

(a)

(b)

(c)

(d)

(e)

Step by step solution

01

Oxymercuration reaction

It is an electrophilic addition reaction that can transform an alkyne into an enol which tautomerizes into a ketone.

(alkyne) (enol) (ketone)

02

Tautomerism

Tautomerism is defined as the phenomenon in which a hydrogen atom is shifted from one place to another. This means that a single chemical compound can exist in two or more interconvertible structures. The making and breaking of a and bond is involved in tautomerism.

03

Formation of products

(a)

(b)

(c)

(d)

(e)

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Most popular questions from this chapter

Question. The mass spectrum of unknown compound A shows a molecular ion at m/z 116 and prominent peaks at m/z 87 and m/z 101. Its UV spectrum shows no maximum above 200 nm. The IR and NMR spectra of A follow. When A is washed with dilute aqueous acid, extracted into dichloromethane , and the solvent evaporated, it gives a product B. B shows a strong carbonyl signal at 1715 cm-1in the IR spectrum and a weak maximum at 274nm(E =16) in the UV spectrum. The mass spectrum of B shows a molecular ion of m/z 72. Determine the structures of A and B, and show the fragmentation to account for the peaks at m/z 87 and 101.

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