A mechanism involving a carbocation rearrangement for the conversion of isoborneol into camphene on treatment with dilute sulfuric acid is to be proposed. Concept introduction: The steps involving a carbocation rearrangement for the conversion of isoborneol into camphene on treatment with dilute sulfuric acid are i) Protonation of the hydroxyl group by sulfuric acid ii) Loss of water to yield a carbocation iii) Migration of a ring carbon to produce a more stable carbocation. iv) Deprotonation. To propose: A mechanism involving a carbocation rearrangement for the conversion of isoborneol into camphene on treatment with dilute sulfuric acid.

Question

For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. ? NH2 MgBr Will the first product that forms in this reaction create a new CC bond? ○ Yes ○ No MgBr ? Will the first product that forms in this reaction create a new CC bond? O Yes O No Click and drag to start drawing a structure. :☐ G x c olo Ar HE

Answer 1

Question

Chapter 27.SE, Problem 16MP

Interpretation Introduction

Interpretation:

A mechanism involving a carbocation rearrangement for the conversion of isoborneol into camphene on treatment with dilute sulfuric acid is to be proposed.

Concept introduction:

The steps involving a carbocation rearrangement for the conversion of isoborneol into camphene on treatment with dilute sulfuric acid are i) Protonation of the hydroxyl group by sulfuric acid ii) Loss of water to yield a carbocation iii) Migration of a ring carbon to produce a more stable carbocation. iv) Deprotonation.

To propose:

A mechanism involving a carbocation rearrangement for the conversion of isoborneol into camphene on treatment with dilute sulfuric acid.

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For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. ? NH2 MgBr Will the first product that forms in this reaction create a new CC bond? ○ Yes ○ No MgBr ? Will the first product that forms in this reaction create a new CC bond? O Yes O No Click and drag to start drawing a structure. :☐ G x c olo Ar HE

Predicting As the lead product manager at OrganometALEKS Industries, you are trying to decide if the following reaction will make a molecule with a new C - C bond as its major product: H₂N O H 1. ? 2. H3O+ If this reaction will work, draw the major organic product or products you would expect in the drawing area below. If there's more than one major product, you can draw them in any arrangement you like. Be sure you use wedge and dash bonds if necessary, for example to distinguish between major products with different stereochemistry. 0 If the major products of this reaction won't have a new CC bond, just check the box under the drawing area and leave it blank. فا Explanation Check Click and drag to start drawing a structure.

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