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Chapter 8: Q60P. (page 460)

Unknown X, C5 H9 Br, does not react with bromine or with dilute KMnO4. Upon treatment with potassium tert-butoxide, X gives only one product, Y, C5 H8. Unlike X, Y decolorizes bromine and changes KMnO4 from purple to brown. Catalytic hydrogenation of Y gives methylcyclobutane. Ozonolysis–reduction of Y gives dialdehyde Z, C5 H8 O2. Propose consistent structures for X, Y, and Z. Is there any aspect of the structure of X that is still unknown?

Short Answer

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Proposed structures with reactions are shown below.

Step by step solution

01

Organic Reactions

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02

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Since compound X (C5H9Br) does not react with bromine or dilute KMnO4 which means compound is saturated (i.e., no double or triple bond is present in the structure X).

Also, X upon treatment with tBuOK gives one product Y. This is the dehydrobromination reaction which results in the removal of hydrogen bromide and double bond formation takes place in compound Y. As now, double bond (unsaturated bond) is present in compound Y, it decolorizes bromine and changes KMnO4 from purple to brown.

Further, catalytic hydrogenation (H2, Pd-C) of Y gives methylcyclobutane. At last, ozonolysis-reduction of Y gives dialdehyde Z (C5H8O2).


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Most popular questions from this chapter

(a) When HBr adds across the double bond of 1,2-dimethylcyclopentene, the product is a mixture of the cis and trans isomers. Show why this addition is not stereospecific.

(b) When 1,2 dimethylcyclopropene undergoes hydroboration oxidation, one diastereomer of the product predominantes. Show why this addition is stereospecific, and predict the stereochemistry of the major product.

Predict the carbenoid addition products of the following reactions.

(a) trans - hex - 3 - ene + CH2I2, Zn(Cu)

(b) cis - hept - 2 - ene + CH2I2, Zn(Cu)

Limonene is one of the compounds that give lemons their tangy odour.Show the structures of the products expected when limonene reacts with an excess of each of these reagents.

(a) Borane in tetrahydrofuran, followed by basic hydrogen peroxide

(b) m-chloroperoxybenzoic acid

(c) ozone, then dimethyl sulfide

(d) a mixture of osmic acid and hydrogen peroxide

(e) hot, concentrated potassium permanganate

(f) peroxyacetic acid in acidic water

(g) hydrogen and a platinum catalyst

(h) hydrogen bromide gas

(i) hydrogen bromide gas in a solution containing dimethyl peroxide

(j) bromine water

(k) chlorine gas

(l) mercuric acetate in methanol, followed by sodium borohydride

(m) CHBr3 and 50% aq. NaOH


The structures of three monomers are shown. In each case, show the structure of the polymer that would result from polymerization of the monomer. Vinyl chloride is polymerized to ‘’vinyl’’ plastics and PVC pipe. Tetrafluoroethylene polymerizes to Teflon, used as non-stick coatings and PTFE valves and gaskets. Acrylonitrile is polymerized to Orlon, used in sweaters and carpets.

Show how you would accomplish each of the following synthetic conversions.

a) Trans-but-2-ene→trans-1,2-dimethylcyclopropane

b) Cyclopentene→

c) Cyclohexanol→
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