Lab 5 - Experiment#5 Experiment#5 Synthesis of 7,7-dichloronocarane Objective The purpose of this experiment is to synthesize 7,7dichloronorcarane

Info iconThis preview shows pages 1–2. Sign up to view the full content.

View Full Document Right Arrow Icon
CHEM 237 Lab Fall 2009 Objective The purpose of this experiment is to synthesize 7,7- dichloronorcarane from a base-promoted reaction of CHCl 5 10 3 with cyclohexene. The reaction involves formation of carbene as a highly reactive intermediate. The reaction progress will be monitored by TLC. Reagents Cyclohexene CHCl3 (Chloroform) 50% NaOH (aq) Saturated NaCl (aq) 15 Ethyl ether Apparatus Erlenmeyer flasks Vials 20 TLC plate (SiO 2 ) Glass pipette and micropipette Graduate Cylinder (10 mL) Theory 25 Synthesis of 7,7-dichloronorcarane from the reaction of chloroform (CHCl 3 )* with cyclohexene in aqueous NaOH solution is shown in Scheme 1. CHCl 3 , aq. NaOH Cl Cl Scheme 1. Synthesis of 7,7-dichloronocarane Phase transfer catalyst (PTC) The mechanism for the synthesis of the product is proposed to involve carbene as a short-lived intermediate (Scheme 2). The acid-base reaction between chloroform and NaOH will produce an inductively stabilized carbanion possessing electrowithdrawing three chloride atoms. 30
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Image of page 2
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 03/03/2010 for the course CHEM 237 taught by Professor Chong during the Fall '10 term at Illinois Tech.

Page1 / 2

Lab 5 - Experiment#5 Experiment#5 Synthesis of 7,7-dichloronocarane Objective The purpose of this experiment is to synthesize 7,7dichloronorcarane

This preview shows document pages 1 - 2. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online