Imagining that the epoxide ring in (2R, 3R)-2, 3-epoxy-3-methylpentane is opened when treated with aqueous acids. a) The structure of the epoxide with stereochemistry is to be drawn. b) The name and structure of the product with stereochemistry are to be given. c) Whether the product is chiral or not is to be explained. d) Whether the product is optically active or not is to be explained. Concept introduction: The acid protonates the epoxide and then water attacks the protonated epoxide to yield the diol . When both epoxide carbons are either primary or secondary the nucleophilic attack of water mainly occurs at the less highly substituted side. When one of the epoxide carbons is tertiary, the nucleophilic attack of water mainly occurs at the more highly substituted side. To draw: The structure of the epoxide with stereochemistry. To give: The name and structure of the product with stereochemistry. To explain: Whether the product is chiral or not and whether the product is optically active or not.

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 18.SE, Problem 50AP

Interpretation Introduction

Interpretation:

Imagining that the epoxide ring in (2R, 3R)-2, 3-epoxy-3-methylpentane is opened when treated with aqueous acids. a) The structure of the epoxide with stereochemistry is to be drawn. b) The name and structure of the product with stereochemistry are to be given. c) Whether the product is chiral or not is to be explained. d) Whether the product is optically active or not is to be explained.

Concept introduction:

The acid protonates the epoxide and then water attacks the protonated epoxide to yield the diol. When both epoxide carbons are either primary or secondary the nucleophilic attack of water mainly occurs at the less highly substituted side. When one of the epoxide carbons is tertiary, the nucleophilic attack of water mainly occurs at the more highly substituted side.

To draw:

The structure of the epoxide with stereochemistry.

To give:

The name and structure of the product with stereochemistry.

To explain:

Whether the product is chiral or not and whether the product is optically active or not.

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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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