Question

CHEM 220L Laboratory Manual (S.A. Cummings & J.K. Mahoney) CHEM 220L Data Sheet: Nucleophilic Substitutions (SN1 and SN2) (6 points) Part 1. Enter the results of each test into the table below: Alkyl Halides 10, 2 or 3? SN2 (Nal/acetone) 1-chlorobutane 1-bromobutane 2-chlorobutane 2-bromobutane bromocyclohexane 2-chloro-2-methylpropane (t-butyl chloride) Crotyl chloride Benzyl chloride (a-chlorotoluene) Arrange the alkyl halides in order of reactivity (from most to least reactive) with Nal/acetone: For those reaction which produced a precipitate: draw the reaction equation with the expected product(s) including stereochemistry if necessary.

Nucleophilic substitutions, mainly just need the arrangements, and the drawn out reaction equations

Answer 1

Past stracture Ichloro butane' ! ; ce 1-bromo butane : Br I - 2-chloro butane 20 2 bromo butanea 'Br Bromo cyclo hexane - Br 2-chloro, 2-methyl propane - crotyl chloride Benzyl chloride

. part-1 Reactivity order for SN? (Nas, Acelone) As the charge density increases and hideeance decteases the > Rate of of SN² also depends on leaving group ability so order of reactivity is Benzyl chloride > Crobyl chloride > 1-Bromo butane Most reactive I-chloro butane v 2- Bromo 2-chloro - butane g. methyl a butarea Рторам Least reactive bromo 9. chloro < cycloheraveni

Part-2 Reactivity Ordee of SN²-.. → As the stability carbocation inteimediate increases the rate of snt increases. → It also depends on leaving group tendeng stability order of cas © Lo > Vº 9XH Resonance 52H 22H V 4CH - D uration 1. Hyper conjugation so order of reactivity Benxyl chloride > Cro yl chloride > 2-chloro q-metlyl РФраиле 2- bromo butane 2-chloro butane 1- chloro I-bromo bu but are < bromo cyclo kenai - < butane