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

(a) Draw the structure of (1E,4R)-1,4-dimethylcyclodecene. (b) Draw the enantiomer and name it, including its E,Z and R,S prefixes. (c) Draw two diastereomers and name them, including the E,Z and R,S prefixes.

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.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

(a) Draw the structure of (1E,4R)-1,4-dimethylcyclodecene. (b) Draw the enantiomer and name it, including its E,Z and R,S prefixes. (c) Draw two diastereomers and name them, including the E,Z and R,S prefixes.

(a) What product(s) are formed when the E isomer of C6H5CH = CHC6H5 is treated with Br2, followed by one equivalent of KOH? Label the resulting alkene(s) as E or Z. (b) What product(s) are formed when the Z isomer of C6H5CH = CHC6H5 is subjected to the same reaction sequence? (c) How are the compounds in parts (a) and (b) related to each other?

When treated with NaOH, the bromide below gives an alkene by the E2 mechanism, by elimination of the H atom indicated by the arrow: (a) Draw the Newman projection from which elimination takes place. (b) Draw the mechanism. (c) Draw the product with the proper stereochemistry. (d) Assign the proper stereochemical descriptor to the product. (e) Give the rate equation