To prepare the given products from the reaction of a ketone with an alkyl halide . Concept introduction: To increase the carbon chain, substituting an alkyl group on alpha carbon of a carbonyl group is called alkylation. Alkylation is carried out by removing a proton from an alpha carbon with a strong base, LDA, to form an enolate ion and then adding an appropriate alkyl halide. The alkylation is a S N 2 reaction. The alkylation works best with a primary alkyl halide.

Question

Draw the most stable chair conformation of 1-ethyl-1-methylcyclohexane, clearly showing the axial and equatorial substituents. [4] Draw structures corresponding to the following IUPAC name for each of the following compounds; [5] i) 4-Isopropyl-2,4,5-trimethylheptane ii) trans-1-tert-butyl-4-ethylcyclohexane iii) Cyclobutylcycloheptane iv) cis-1,4-di-isopropylcyclohexane (chair conformation) v) 3-Ethyl-5-isobutylnonane

Answer 1

Question

Chapter 17.7, Problem 14P

(a)

Interpretation Introduction

Interpretation: To prepare the given products from the reaction of a ketone with an alkyl halide.

Concept introduction: To increase the carbon chain, substituting an alkyl group on alpha carbon of a carbonyl group is called alkylation.

Alkylation is carried out by removing a proton from an alpha carbon with a strong base, LDA, to form an enolate ion and then adding an appropriate alkyl halide. The alkylation is a SN2 reaction. The alkylation works best with a primary alkyl halide.

(b)

Interpretation Introduction

Interpretation: To prepare the given products from the reaction of a ketone with an alkyl halide.

Concept introduction: To increase the carbon chain, substituting an alkyl group on alpha carbon of a carbonyl group is called alkylation.

Alkylation is carried out by removing a proton from an alpha carbon with a strong base, LDA, to form an enolate ion and then adding an appropriate alkyl halide. The alkylation is a SN2 reaction. The alkylation works best with a primary alkyl halide.

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