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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

In the absence of water, ophthalaldehyde has the structure shown. Its strong IR absorption is at 1687 cm-1; the proton NMR data are shown by the structure. In the presence of water, a new compound is formed that has a strong IR absorption around 3400 cm-1 and no absortion in the C=0 region. propose a structure of X consistent with this information and suggest how X consistent with this information and suggest how X was formed.

Predict the products of the following reactions.

Show how you would synthesize each compound from starting materials containing no more than six carbon atoms.

(a)

(b)

(c)

Question. The UV spectrum of an unknown compound shows values ofat 225 nm(E = 10,000) and at 318 nm(E = 40). The mass spectrum shows a molecular ion at m/z 96 and a prominent base peak at m/z68. The IR and NMR spectra follow. Propose a structure, and show how your structure corresponds to the observed absorptions. Propose a favorable fragmentation to account for the MS base peak at m/z 68 (loss of C2H4 ).

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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