ORGO EXAM 3 Alcohol Reactions

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9 Terms

1
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mechanism: acid halides

oxygen lone pair attacks H+ (protonation) to form H2O

2
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outcome: acid halides

H2O leaves, halide attacks. halide replaces

3
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stereochemistry: acid halides

carbocation intermediate for secondary and tertiary alcohol

inversion of stereochemistry and retention

4
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conversion: PBr3

primary and secondary alcohols to alkyl bromides

5
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mechanism: PBr3

alcohol attacks phosphorus atom. Br replaces alcohol

6
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stereochemistry: PBr3

proceeds SN2 - inversion

7
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conversion: thionyl chloride (SOCl2/pyridine)

converts primary and secondary alcohols to alkyl chlorides

8
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mechanism: thionyl chloride (SOCl2/pyridine)

alcohol attacks SO to create chlorosulfite intermediate

pyridine absorbs excess HCl

Cl attacks

Cl replaces OH

9
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stereochemistry: thionyl chloride (SOCl2/pyridine)

SN2 - inversion