How could the following compounds be prepared, using cyclohexene as a starting material?
d.

Show how you would synthesize the following compound from alkyl halides, vinyl halides, and aryl halides containing no more than six carbon atoms.

(c) trans-oct-3-ene

Show how you would synthesize the following compound from alkyl halides, vinyl halides, and aryl halides containing no more than six carbon atoms.

(a) octane

Predict the major products of the following reactions, including stereochemistry where appropriate.

(h) cyclooctylmethanol + CH₃CH₂MgBr

(i) potassium tert-butoxide + methyl iodide

(j) sodium methoxide + tert-butyl iodide

Which of the following alkyl halides could be successfully used to form a Grignard reagent?

A laboratory student added 1-bromobutane to a flask containing dry ether and magnesium turnings. An exothermic reaction resulted, and the ether boiled vigorously for several minutes. Then she added acetone to the reaction mixture and the ether boiled even more vigorously. She added dilute acid to the mixture and separated the layers. She evaporated the ether layer, and distilled a liquid that boiled at 143 °C. GC–MS analysis of the distillate showed one major product with a few minor impurities. The mass spectrum of the major product is shown here.

(a) Draw out the reactions that took place and show the product that was formed.

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Starting with cyclohexane, how could the following compounds be prepared?

e.

A chemist attempted the reaction below, one we introduce in Chapter 17, expecting the reaction between a strong nucleophile and a ketone in water to give an alkoxide product.

(a) Why did the reaction fail?

(b) How could the reaction conditions be changed to give a successful reaction?

Give the expected products of the following reactions. Include a protonation step where necessary.

(a) 2,2-dimethyloxirane + isopropylmagnesium bromide

(b) propylene oxide + n-butyllithium

(c) cyclopentyloxirane + ethyllithium