Alcohol, Phenols, Thiols, and Ethers

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Alcohol, Phenols,

Thiols, and Ethers


• Classification of Alcohols
• Naming Alcohols, Phenols, Thiols and Ethers
• Physical Properties
Contents • Preparation of Alcohols
• Chemical Properties
• Important Alcohols
• Society and culture
Alcohols, Phenols, Thiols
Classification of Alcohols
A – according to the number of –OH group (hydroxyl group)
• Monohydric Alcohols – contain only one –OH group, ex. CH3CH2OH (ethyl alcohol)
• Dihydric Alcohols – contains 2 –OH group, ex. Ethylene glycol HOCH2CH2OH
• Trihydric Alcohols – contains 3 -OH group, ex. Glycerol
Classification of Alcohols
B – according to the location of the –OH group (hydroxyl group)
Naming Alcohols
• IUPAC
• The rules for naming alkanes is applied with the addition of:
• Characteristics ending is “ol”
• Position of the –OH is indicated by the lowest number
Naming Phenols
Naming Thiols
Naming Ether
Physical Properties
Physical Properties
Physical Properties
• Solubility table of simple alcohols and ethers
Physical Properties
Preparation of Alcohols
A. Primary Alcohols
q Displacement of Halide ion
RCH2X + HOH RCH2OH + HX
qReduction of carbonyl group R-C=O
RCHO + LiAlH4 RCH2OH ether as catalyst (same rxn with carboxylic acid, esters)
qHydration of Olefins
H2C=CH2 + H2O CH3CH2OH H2SO4 as catalyst
qDeborane Method
CH3CH2CH=CH2 + B2H6 2(CH3CH2CH2CH2)3B
2(CH3CH2CH2CH2)3B + H2O2 6CH3CH2CH2CH2OH + H3BO3
qGrignard Reaction
RMgX + HCHO RCH2OMgX RCH2OMgX + HOH RCH2OH + Mg(OH)X
qFermentation of Sugar
Sucrose Glucose CH3CH2OH + HOH
Preparation of Alcohols
B. Secondary Alcohols
q Reduction of Ketones
CH3COCH3 + LiAlH4 4CH3CHOHCH3 in ether
q Hydration of Olefins
CH3CH=CH2 + HOH CH2CHOHCH3 in H2SO4
q Grignard Reaction (all other aldehydes except for formaldehyde HCHO)
CH3CHO + RMgX CH3CHOMgX + HOH CH3CHOH-R +Mg(OH)X
Preparation of Alcohols
C. Tertiary Alcohols
Chemical Properties of Alcohols
• Salt Formation (RCH2OH + Na RCH2ONa + H2)
• Dehydration (CH3CH2OH + CaC2 CH3CH2OH + acetylene + Ca(OH)2)
• Test for water in ROH
• Replacement of hydroxyl group with halides
• With PX3
• With SOCl2
• With Lucas Reagent
• Oxidation Reactions
• Esterification Reaction

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