CHEM152L(7_09_09)

CHEM152L(7_09_09) - Summer 2009 Reactions Involving Allylic...

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CHEM 152L Summer 2009 17.1. Reactions Involving Allylic and Benzylic Carbocations allylic carbocations can be thought of the same way – What are the typical reactions that these types of compounds undergo? If we compare rates of SN1 solvolysis rates of allylic and nonallyic halides – we see the following trend Similarly compare benzylic and nonbenzylic SN1 solvolysis rates – Look at how substituents help to enhance the rate of SN1 reactions by extra resonance –
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CHEM 152L Summer 2009 Reactions Involving Allylic and Benzylic Radicals – similar stability is seen with allylic and benzylic radicals Ultimately we see substitution reactions rather than addition reactions with radical conditions – we can take advantage of the stability of allylic and benzylic radicals EX.
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CHEM 152L
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Unformatted text preview: Summer 2009 Reactions Involving Allylic and Benzylic Anions – more stable as a result of resonance. Allylic Grignards - resonance stabilized carbanion – asymmetric species may give rise to some regiochemical consequences E2 elimination involving benzylic and allylic hydrogens CHEM 152L Summer 2009 Allylic and Benzylic SN2 Reactions – enhanced as well (how do we promote SN2 over SN1 reactivity?) Benzylic Oxidation of Alkylbenzenes – interesting that we can oxidize alkyl side chains to carboxylic acids regardless of length of side chain – MUST have a benzylic hydrogen CHEM 152L Summer 2009 Terpenes – Isoprene Rule – fact that all terpenes contain same 5-carbon skeleton 5 carbon skeleton of isoprene some common terpenes – and a look at their structures –...
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