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Chapter 16: Problem 22

With organolithium and organomagnesium compounds, approach to the carbonyl carbon from the less hindered direction is generally preferred. Assuming this is the case, predict the structure of the major product formed by reaction of methylmagnesium bromide with 4-tertbutylcyclohexanone.

Short Answer

Expert verified
Answer: The major product of the reaction between methylmagnesium bromide and 4-tertbutylcyclohexanone is 4-(tert-butyl)cyclohexanol with a methyl group on the less hindered side of the starting carbonyl group.

Step by step solution

01

Draw the Structure of 4-tertbutylcyclohexanone

Begin by drawing the structure of 4-tertbutylcyclohexanone. This molecule has a cyclohexanone ring with a carbonyl group (=O) and a tert-butyl group attached to the fourth carbon of the ring.
02

Identify the Less Hindered Side

We need to identify the less hindered side of the carbonyl group. Since the tert-butyl group contains three methyl groups, it creates significant steric hindrance on one face of the molecule. The carbonyl carbon thus will be less hindered on the opposite side, away from the tert-butyl group.
03

Draw the Structure of Methylmagnesium Bromide

Methylmagnesium bromide is an organomagnesium reagent, commonly known as a Grignard reagent, with the formula CH3MgBr. Draw its structure with a single bond between the carbon and magnesium atoms and a single bond between magnesium and the bromine atom.
04

Predict the Major Product

Knowing that organometallic reagents prefer to approach the carbonyl carbon from the less hindered direction, the methyl group from methylmagnesium bromide will attack the carbonyl carbon, and the carbonyl bond will shift to form a new O-MgBr bond. This results in an alkoxide intermediate, which, after quenching with an acidic workup, yields the corresponding alcohol as the major product. The final product will be 4-(tert-butyl)cyclohexanol with a methyl group on the less hindered side of the starting carbonyl group.

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Most popular questions from this chapter

Starting with acetylene and 1-bromobutane as the only sources of carbon atoms, show how to synthesize the following. (a) meso-5,6-Decanediol (b) racemic 5,6 -Decanediol (c) 5-Decanone (d) 5,6 -Epoxydecane (e) 5-Decanol (f) Decane (g) 6-Methyl-5-decanol (h) 6-Methyl-5-decanone

Draw a structural formula for the product formed by treating butanal with each reagent. (a) \(\mathrm{LiAlH}_{4}\) followed by \(\mathrm{H}_{2} \mathrm{O}\) (b) \(\mathrm{NaBH}_{4}\) in \(\mathrm{CH}_{3} \mathrm{OH} / \mathrm{H}_{2} \mathrm{O}\) (c) \(\mathrm{H}_{2} / \mathrm{Pt}\) (d) \(\mathrm{Ag}\left(\mathrm{NH}_{3}\right)_{2}{ }^{+}\)in \(\mathrm{NH}_{3} / \mathrm{H}_{2} \mathrm{O}\) (e) \(\mathrm{H}_{2} \mathrm{CrO}_{4}\), heat (f) \(\mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{OH}, \mathrm{HCl}\) (g) \(\mathrm{Zn}(\mathrm{Hg}) / \mathrm{HCl}\) (h) \(\mathrm{N}_{2} \mathrm{H}_{4}, \mathrm{KOH}\) at \(250^{\circ} \mathrm{C}\) (i) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}\) (j) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NHNH}_{2}\)

If the Favorskii rearrangement of 2-chlorocyclohexanone is carried out using sodium ethoxide in ethanol, the product is ethyl cyclopentanecarboxylate.

Starting with cyclohexanone, show how to prepare these compounds. In addition to the given starting material, use any other organic or inorganic reagents as necessary. (a) Cyclohexanol (b) Cyclohexene (c) cis-1,2-Cyclohexanediol (d) 1-Methylcyclohexanol (e) 1-Methylcyclohexene (f) 1-Phenylcyclohexanol (g) 1-Phenylcyclohexene (h) Cyclohexene oxide (i) trans-1,2-Cyclohexanediol

Using your roadmaps as a guide, show how to convert 1-butanol into racemic 4-octanol. You must use 1-butanol as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way.
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