Experiment 9 - Vanessa Chew Ashleigh Ward Chem 3AL November...

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

View Full Document Right Arrow Icon
Vanessa Chew Ashleigh Ward Chem 3AL November 28, 2010 Experiment 8: Nucleophilic Substitution Reactions of Alkyl Halides Discussion Most substrates reacted as expected. 1-bromopentane and 1-chloropentane, being primary alkyl halides, reacted with NaI/acetone via S N 2, but did not react under the S N 1 conditions, AgNO 3 /EtOH, as simple primary carbocations are too unstable and do not form. Secondary alkyl halides demonstrated more varied results. 2-bromopentane and 3-bromopentane both reacted via S N 1 and S N 2. A cyclic variant, bromocyclopentane, reacted via S N 2 only upon heating, but reacted via S N 1 easily; bromocyclohexane only reacted via S N 1. All tertiary alkyl halides showed no reaction under S N 2 conditions, as steric hindrance prevented backside attack. 2-chloro-2- methylpropane and 1-bromoadamantane reacted via S N 1, as typical of tertiary alkyl halides, but 1-chloroadamantane did not. Other anomalies include primary alkyl halides 1-bromo-2- methylpropane, which reacted under both conditions despite, and 1-bromo-2,2-dimethylpropane, which did not react via S N 1. Schemes of all reactions are illustrated in Figure 1 . Reaction rates varied within the same mechanism. Within the bromopentane series, via
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 11/29/2010 for the course CHEM 3AL taught by Professor Li during the Fall '08 term at University of California, Berkeley.

Page1 / 5

Experiment 9 - Vanessa Chew Ashleigh Ward Chem 3AL November...

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