Reaction of HBr with 3-methylcyclohexene yields four products: and trans-1-bromo-2-methylcyclohexene. But an analogous reaction of HBr with 3-bromocyclohexene gives trans -1,2-dibromocyclohexane as the sole product. The structures of possible intermediates are to be drawn and further why only a single product is formed in the case of 3-bromocyclohexene is to be explained. Concept introduction: The reaction of HBr with cycloalkenes occurs in two steps. In the first step the Ï€ electrons of the double bond in the cycloalkenes attack the positively polarized hydrogen of HBr to yield a carbocation. In the second step the carbocation being planar can be attacked by the bromide ion from both sides to give different products. To draw: The structures of the possible intermediates in the reactions of HBr with 3-methylcyclohexene and 3-bromocyclohexene and to explain why the former gives cis- and trans -1-bromo-2-methylcyclohexenes while 3-bromocyclohexene gives trans -1,2-dibromocyclohexane as the sole product.

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> You are trying to decide if there is a single reagent you can add that will make the following synthesis possible without any other major side products: 1. ☑ CI 2. H3O+ O Draw the missing reagent X you think will make this synthesis work in the drawing area below. If there is no reagent that will make your desired product in good yield or without complications, just check the box under the drawing area and leave it blank. Click and drag to start drawing a structure. Explanation Check ? DO 18 Ar B © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibility

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Chapter 8.SE, Problem 69AP

Interpretation Introduction

Interpretation:

Reaction of HBr with 3-methylcyclohexene yields four products: and trans-1-bromo-2-methylcyclohexene. But an analogous reaction of HBr with 3-bromocyclohexene gives trans-1,2-dibromocyclohexane as the sole product. The structures of possible intermediates are to be drawn and further why only a single product is formed in the case of 3-bromocyclohexene is to be explained.

Concept introduction:

The reaction of HBr with cycloalkenes occurs in two steps. In the first step the Ï€ electrons of the double bond in the cycloalkenes attack the positively polarized hydrogen of HBr to yield a carbocation. In the second step the carbocation being planar can be attacked by the bromide ion from both sides to give different products.

To draw:

The structures of the possible intermediates in the reactions of HBr with 3-methylcyclohexene and 3-bromocyclohexene and to explain why the former gives cis- and trans-1-bromo-2-methylcyclohexenes while 3-bromocyclohexene gives trans-1,2-dibromocyclohexane as the sole product.

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> You are trying to decide if there is a single reagent you can add that will make the following synthesis possible without any other major side products: 1. ☑ CI 2. H3O+ O Draw the missing reagent X you think will make this synthesis work in the drawing area below. If there is no reagent that will make your desired product in good yield or without complications, just check the box under the drawing area and leave it blank. Click and drag to start drawing a structure. Explanation Check ? DO 18 Ar B © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibility

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Consider a solution of 0.00304 moles of 4-nitrobenzoic acid (pKa = 3.442) dissolved in 25 mL water and titrated with 0.0991 M NaOH. Calculate the pH at the equivalence point