Tag : Stereochemistry

A Study of Regiochemistry and Stereochemistry in the Hydroboration-Oxidation of (1R)-(+)--Pinene

By: Ryan DeAngelis, Andrew Mound Introduction The purpose of this experiment is to synthesize an alcohol using hydroboration-oxidation and determine the regiochemistry and stereochemistry of the product via 1H-NMR, 13C-NMR, and Infrared spectroscopy.1 Hydroboration-Oxidation is a two-step process used to convert an alkene to an alcohol. The first step, hydroboration, is the addition of borane (BH3) to the alkene. It proceeds as a concerted mechanism with the electron pair in the pi bond attacking the electrophilic boron, and one of […]

Stereochemistry of Bromine Addition to an Alkene

Written by Aarti Prabhu Objective: To be able to conduct a reflux reaction, and practice improving recrystallization and mp determination, by the bromination of trans-cinnamic acid to form 2,3-dibromo-3-phenylpropanoic acid, and connect syn and anti addition concepts and stereochemical consequences (erythro & threo) from the addition mechanism. PROCEDURE: Procedure: Observations: Combine 100 mg of trans cinnamic acid in a 4 mL conical vial. 0.1025 g of trans cinnamic acid was added. Add 0.7 mL of dichloromethane and 350 uL of […]