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Chapter 9: Q21P (page 486)

For each compound, give the product(s) expected from (1) HgSO4/H2SO4– catalyzed hydration and (2) hydroboration–oxidation.

(a) hex-1-yne

(b) hex-2-yne

(c) hex-3-yne

(d) cyclodecyne

Short Answer

Expert verified

Alkyne is hydrated using the Kucherov reaction using the reagent dilute sulphuric acid and special reagent mercury sulfate HgSO4/H2SO4 .

Hydration of alkyne follows Markovnikov's rule, and intermediate enol is formed during the reaction.

Step by step solution

01

Hydration of Alkyne

Alkyne is hydrated using the Kucherov reaction using the reagent dilute sulphuric acid and special reagent mercury sulfate HgSO4/H2SO4 .

Hydration of alkyne follows Markovnikov's rule, and intermediate enol is formed during the reaction.

02

Products from HgSO4/H2SO4 - catalyzed hydration

(a) HgSO4/H2SO4catalyzed reaction of hex-1-yne from hex-2-one product.


(b) HgSO4/H2SO4catalyzed reaction of hex-2-yne from a mixture of two products hex-2-one and hex-3-one.

(c) HgSO4/H2SO4catalyzed reaction of hex-3-yne from hex-3-one product

(d) HgSO4/H2SO4catalyzed reaction of cyclodecyne forms cyclodecaone product.

03

Products from the hydroboration oxidation reaction

(a) Hydroboration oxidation reaction of hex-1-yne from hexanone product.

The hydroboration oxidation reaction of (a)

(b) Hydroboration oxidation reaction of hex-2-yne from a mixture of two products hex-2-one and hex-3-one.

(c) Hydroboration oxidation reaction of hex-3-yne from hex-3-one product.

(d) Hydroboration oxidation reaction of cyclodecyne forms cyclodecaone product

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Most popular questions from this chapter

Write structural formulas for the following compounds (includes both old- and new-style names).

(a) 2-octyne (b) ethyl isopentyl acetylene (c) ethynylbenzene

(d) cyclohexyl acetylene (e) 5-methyl-3-octyne (f) trans-3,5-dibromocyclodecyne

(g) 5,5-dibromo-4-phenylcyclooct-1-yne (h) (E)-6-ethyloct-2-en-4-yne

(i) 1,4-heptadiyne (j) vinylacetylene (k) (S)-3-methyl-1-penten-4-yne

Question:Predict the products of the reaction of but-1-yne with the following reagents.

(a)1 equivalent of HCl

(b)2 equivalents of HCl

(c)excess H2 , Ni

(d) H2 , Pd /BaSO4, quinolone

(e)1 equivalent of Br2

(f)2 equivalents of Br2

(g)cold, dilute KMnO4

(h)warm, concd.KMnO4 , NaOH

(i)Na, liquid ammonia

(j) NaNH2

(k) H2SO4/HgSO4, H2O

(l) Sia2BH, then , H2O2,OH-

Show how hex-1-yne might be converted to

(a) 1,2-dichlorohex-1-ene. (b) 1-bromohex-1-ene.

(c) 2-bromohex-1-ene. (d) 1,1,2,2-tetrabromohexane.

(e) 2-bromohexane. (f) 2,2-dibromohexane.

Question:When treated with hydrogen and a platinum catalyst, an unknown compound X absorbs 5 equivalents of hydrogen to give n-butylcyclohexane. Treatment of X with an excess of ozone, followed by dimethyl sulfide and water, gives the following products:

Propose a structure for the unknown compound X. Is there any uncertainty in your structure?

Oxidative cleavages can help to determine the positions of the triple bonds in alkynes.

(a) An unknown alkyne undergoes oxidative cleavage to give adipic acid and two equivalents of acetic acid. Propose a structure for the alkyne.

(b) An unknown alkyne undergoes oxidative cleavage to give the following triacid plus one equivalent of propionic acid. Propose a structure for the alkyne.
See all solutions

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