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McGill University
Biology (Sci)
BIOL 200
Karine Auclair

Chemistry 212 Fall 2013 Experiment 3: S N – Evaluation Summary Last Name:Atique First Name:Anika Date: 11/05/2013 Lab Day/TA/Group: Wednesday; TA: Patrick Julien; Group C Lab reports must be typed and chemical structures must be drawn with ChemDraw. Report must not exceed five pages (including this page). Page limit does not include any attached spectra or references. ** Deductions for hand written report/structures and exceeding page limit ** Report Breakdown Data/Results: _________________ /10 Discussion: _________________ /10 Report Total: _________________ /20 Other Lab Marks Performance: _________________ /6 Prelab Quiz: _________________ /3 TAComments on Report/Performance Report assessment TA(name): TA(signature): Performance assessment TA(name): TA(signature): 1 of 5 Chemistry 212 Fall 2013 Experiment 3: S 1N– Report Sheet Last Name:Atique First Name:Anika Date:11/05/2013 Lab Day/TA/Group: Wednesday; Patrick Julien, Group C Objective: (1 mark) (What is the purpose of this experiment?) To investigate the reaction mechanism via SN1 during the conversion of an alcohol2,5-dimethyl- 2,5-hexanediol) to an alkyl chloride (2,5-dichloro-2,5-dimethylhexane) Introduction: (2 marks) (Brief description of the concept/reaction studied N S 1 reactions – and why it is important) SN1 is a nucleophilic substitution reaction where the rate determining step is the formation of the carbocation via the cleavage of the carbon-leaving group. The reaction involves multiple steps, and is unimolecular, with only the concentration of electrophile determining the rate and not the nucleophile. SN1 is important because it provides a pathway for tertiary alcohol which have high steric hindrance to undergo substitution reaction. The high steric hindrance prevents it from going though an SN2 mechanism. In this experiment the OH group is protonated by HCl to make it a good leaving group H2O+. The rate determining step is the cleavage of this leaving group bond with carbon which results in the formation of a carbocation that is rapidly attacked by the nucleophile present in the vessel, Cl-, to form the product. Reaction Equation: (2 marks) (Equation and data [molar mass, concentration, density, volume, mass, moles, etc – as appropriate – including theoretical yield] for reactants and products) Materials Molar Quantity Density Concentrat Moles/ Molar Theoretic mass (g/ml) ion mmol ratio al yield (g/mol) 2,5-dimethyl- 146.2 .25g 1.71 1 2,5-hexandiol HCl 36.5 2ml 1.2 65.7 1 2 Chemistry 212 Fall 2013 2,5-dichloro- 183 1.71 1 .31g 2,5- methylhexane Table 1. Results – Yield and Physical Properties of SN1 Product (2 marks) 2,5-Dichloro-2,5-Dimethylhexane Yield (g) .24g Yield (%) 77.4
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