Epoxides are highly strained and can alleviate the strain by reacting under acidic and basic conditions to give different regiochemical and stereochemical products. In this epoxide tutorial, we will cover 1. ring opening of unsubstituted epoxide 2. which nucleophiles will open an epoxide 3. regiochemical and stereochemical results of basic ring opening of asymmetrical epoxides 4. regiochemical and stereochemical results of acidic ring opening Step 3: If the nucleophilic attack takes place on a chiral epoxide, an inversion of configuration is observed. Consider the epoxide ring-opening of a chiral epoxide. 1. NaSH ? 2. H₂O Select the product or products of the reaction. SH SH SH JOH ...OH OH OH .....SH

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter13: Substitution
Section: Chapter Questions
Problem 54CTQ
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Epoxides are highly strained and can alleviate the strain by
reacting under acidic and basic conditions to give different
regiochemical and stereochemical products. In this epoxide
tutorial, we will cover
1. ring opening of unsubstituted epoxide
2. which nucleophiles will open an epoxide
3. regiochemical and stereochemical results of basic ring
opening of asymmetrical epoxides
4. regiochemical and stereochemical results of acidic
opening
Step 3: If the nucleophilic attack takes place on a chiral
epoxide, an inversion of configuration is observed.
Consider the epoxide ring-opening of a chiral epoxide.
O
1. NaSH
?
2. H₂O
Select the product or products of the reaction.
SH
SH
SH
OH
.....OH
OH
JOH
SH
Transcribed Image Text:Epoxides are highly strained and can alleviate the strain by reacting under acidic and basic conditions to give different regiochemical and stereochemical products. In this epoxide tutorial, we will cover 1. ring opening of unsubstituted epoxide 2. which nucleophiles will open an epoxide 3. regiochemical and stereochemical results of basic ring opening of asymmetrical epoxides 4. regiochemical and stereochemical results of acidic opening Step 3: If the nucleophilic attack takes place on a chiral epoxide, an inversion of configuration is observed. Consider the epoxide ring-opening of a chiral epoxide. O 1. NaSH ? 2. H₂O Select the product or products of the reaction. SH SH SH OH .....OH OH JOH SH
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