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z-Ch. 17 Alcohol Reactions
CHM2211 Dr. Elsheimer Fall 09
25
Organic Chemistry
Undergraduate 2
09/17/2009

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Term
Hydration of Alkenes (Non-Markovnikov)
Definition
1. BH3/THF 2. H2O2/-OH (R-CH=CH-R)->(R-OH-CH-CH2-R)
Term
Hydration of Alkenes (Markovnikov)
Definition
1. Hg(OAc)2/H2O 2. NaBH4 (R-CH=CH-R)->(R-CH2-CH-OH-R)
Term
Hydroxylation of Alkenes (trans)
Definition
1. RCO3H/CH2Cl2 2. H3O+ (R-CH=CH-R)->(R-OH-CH-CH-OH-R) TRANS
Term
Hydroxylation of Alkenes (cis)
Definition
1. OsO4/Pyridine 2. NaHSO3/H2O (R-CH=CH-R)->(R-OH-CH-CH-OH-R) CIS
Term
Aldehyde + [H]
Definition
Primary Alcohol
Term
Ketone + [H]
Definition
Secondary Alcohol
Term
Carboxylic Acid + [H]
Definition
Primary Alcohol
Term
Ester + [H]
Definition
Primary Alcohol
Term
1. NaBH4/ethanol 2. H3O+
Definition
Reduction of Aldehydes and Ketones
Term
1. LiAlH4/ether 2. H3O+
Definition
Reduction of Aldehydes, Ketones, Esters, and Carboxylic Acids
Term
Grignard Reagents
Definition
RMgBr + R'C=O -> HO-C-RR'

Does not work with carboxylic acid
RMgBr + R'CO2 -> R'CO2- + MgBr+ + RH
Term
Conversion of Alcohols to Alkyl Halides
Definition
SOCl2/ether PBr3/ether p-TosCl/pyridine
Term
SOCl2/ether
Definition
Adds Cl to 1* or 2* alcohol. Sn2 attacks opposite side of leaving group. see pg. 618
Term
PBr3/ether
Definition
Adds Br to 1* or 2* alcohol. Sn2 attacks opposite side of leaving group. see pg. 618
Term
p-TosCl/pyridine
Definition
Replaces OH see pg. 618
Term
Conversion of Alcohols into Esters
Definition
ROH/Strong Acid, heat or 1.SOCl2/2.CH3OH (R'-C=O-OH -> R'-C=O-O-R)
Term
Dehydration of Alcohols
Definition
POCl3/Pyridine or H3O+,THF/50 C (not as good)
Term
Oxidation of Alcohols
Definition
Primary alcohol -> Aldehyde -> Carboxylic Acid

Will NOT react with Tertiary alcohols
Term
PCC/CH2Cl2
Definition
Oxidation. Will convert primary alcohols to aldehydes.
Term
CrO3/H3O+,acetone
Definition
Oxidation. Will convert primary alcohols to carbocylic acid.
Term
Protection of Alcohols
Definition
(CH3)3SiCl/(CH3CH2)3N remove with H3O+
Term
Dehydrogenating an Alcohol
Definition
R-OH Na+H- -> R-O- Na+ H2(gas)
Term
Benzoquinones to Hydroquinone
Definition
SnCl2/H2O
Term
Hydroquinone to Benzoquinones
Definition
Fremy's salt
Term
Phenols to Benzoquinones
Definition
(KSO3)2NO/H2O
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