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Chapter 9: Q38P (page 495)

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?

Short Answer

Expert verified

Answer

Compound X

Step by step solution

01

About n-butylcyclohexane

The organic compound that bears butyl and cyclohexane ring is n-butylcyclohexane. This compound has a molecular formula . The molecular weight of this compound is 140.27 g/mol.

02

About dimethyl sulfide

The organosulfur compound that bears two methyl groups attached to a sulfur atom is dimethyl sulfide. This compound has a disagreeable odor and exists in a liquid state that is highly flammable.

03

About the reaction

The given reaction says that the hydrogen consumed in the reaction is 5 equivalent. So, there must be five pi bonds in the carbon skeleton of compound X. But, the given information is not sufficient to predict the given compound X is cis or trans.

The reaction mechanism is shown below.

Mechanism of the reaction

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Most popular questions from this chapter

Develop syntheses for the following compounds, using acetylene and compounds containing no more than four carbon atoms as your organic starting materials.

(a) 3-methylnon-4-yn-3-ol (“3-ol” means there is an OH group on C3.)

(b) cis-1-ethyl-2-methylcyclopropane

(c)

(d) meso-hexane-3,4-diol

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

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.

Question: Predict the products formed when CH3CH2-C≡C:Na+ reacts with the following compounds.

(a)ethyl bromide

(b)tert-butyl bromide

(c)formaldehyde

(d)cyclohexanone

(e)CH3CH2CH2CHO

(f)cyclohexanol

(g)butan-2-one,CH3CH2COCH3

Deduce the structure of each compound from the information given. All unknown in this problem have molecular formula C8H12.

(a)Upon catalytic hydrogenation, unknown Wgives cyclooctane. Ozonolysis of W,followed by reduction with dimethylsulfide, gives octanedioic acid,HOOC-(CH2) 6-COOH . Draw the structure of W.

(b)Upon catalytic hydrogenation, unknown Xgives cyclooctane. Ozonolysis of X,followed by reduction with dimethyl sulfide, gives two equivalents of butanedial , O =CH -CH2 CH 2-CH = O. Draw the structure of X.

(c) Upon catalytic hydrogenation, unknown Y gives cyclooctane. Ozonolysis of Y, followed by reduction with dimethyl sulfide, gives a three-carbon dialdehyde and a five-carbon dialdehyde. Draw the structure of Y.

(d) Upon catalytic hydrogenation, unknown Z gives cis-bicyclo[4.2.0]octane. Ozonolysis of Z, followed by reduction with dimethyl sulfide, gives a cyclobutane with a three-carbon aldehyde (-CH2-CH2-CHO ) group on C1 and a one-carbon aldehyde (CHO) group on C2. Draw the structure of Z.
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