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Chapter 9: Alcohols Review
1. Classification of alcohols
Classify each OH group in Nasacort, a glucocorticosteroid used as an anti-inflammatory drug.
2. Nomenclature of alcohols
Give the common name for the following alcohols.
Give the IUPAC name for the following alcohols.
3. Boiling point of alcohols
Rank the following compounds in order of increasing boiling point.
Lowest B.pt < < < < Highest B.pt
Lowest B.pt < < < < Highest B.pt
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4. Preparation of alcohols
Nucleophile substitution reactions (SN1/SN2):
Identify the reagents that you would use to prepare following alcohols.
5. Acid-base reaction of alcohols
6. Dehydration of alcohols to alkenes
H2SO4 or TsOH
β-elimination reaction:
Acid converts bad leaving group into a good leaving group:
More substituted alcohols dehydrate more readily:
Zaitsev rule:
E1 mechanism:
E2 mechanism:
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Carbocation Rearrangements:
POCl3/pyridine
Cleaner reaction.
E2 mechanism.
No rearrangements.
Zaitsev rule.
What alkenes are formed when alcohol X is dehydrated under following conditions?
7. Conversion of alcohols to alkyl halides:
HX (X=Cl, Br, I)
Nucleophilic Substitution Reaction:
Acid converts bad leaving group into a good leaving group:
Cl-, Br-, I- become available as nucleophiles.
SN1 mechanism:
SN2 mechanism:
Alkyl halides produced can undergo further substitution or elimination reactions:
