Experiment 6 Nucleophilic Substitution.docx - Experiment 6...

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Experiment 6Unimolecular and Bimolecular Nucleophilic Substitution ReactionLukas SegrovesSection 018Drawer #108Kenny NguyenNovember 15th, 2017PurposeThe purpose of this experiment is to synthesize t-amyl chloride and determine the reactivity of various alkyl halides.Introduction
Segroves 1Unimolecular reactions (Sn1) and bimolecular reactions (Sn2) are two types of nucleophilic substitution reactions.1 In organic chemistry, nucleophilic substitution reactions are when an electron rich nucleophile selectively bonds with or attacks the positive charge of an electrophile to replace a leaving group.2The Sn1 reaction is a stepwise reaction where the leavinggroup leaves first forming a carbocation intermediate that is attacked by a nucleophile. This reaction favors a tertiary carbocation and tends to proceed with weak nucleophiles which are usually neutral compounds. It also favors polar protic solvents such as water, alcohols, and carboxylic acid.3The Sn2 reaction is a single step reaction in which the nucleophile attacks the halogenated alkane while the leaving group dissociates away from it.1It favors primary carbocation and reacts better with strong nucleophiles that are negatively charged. This reaction also favors polar aprotic solvents such as acetone, DMSO, and DMF.3In this experiment, the alkyl halides: 1-chlorobutane, 2-chlorobutane, 2-chloro-2-methylpropane, 1-bromobutane, 3-chloropropane, and chlorobenzene were tested as substrates in Sn1 and Sn2 reactions in order to see which is more effective for each reaction.

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