Alcohols, Phenols, and Ethers
Alcohols, Phenols, and Ethers
Chapter Objectives
1.What is the general structure for an alcohol? A phenol? An ether? 2.What are functional groups? Why are they useful in the study of organic chemistry? 3.What structural feature is used to classify alcohols as primary, secondary, or tertiary? 4.How are alcohols named by the common and IUPAC systems? 5.Why are the boiling points of alcohols higher than those of ethers and alkanes of similar molar masses?
Objectives Cont
6.Why are alcohols and ethers of four carbons or less soluble in water while comparable alkanes are not? 7.How are alcohols prepared from alkenes? What is Markovnikov's rule? 8.How do various alcohols affect the human body? 9.What are the major reactions of alcohols? 10.What product is formed by the oxidation of a primary alcohol? A secondary alcohol? A tertiary alcohol?
Objectives Cont
11.Describe the structure and uses of some common polyhydric alcohols. 12.Describe the structure and uses of some phenols. 13.How does the structural difference between alcohols and ethers affect their physical characteristics and reactivity? 14.How are simple ethers named? Describe the structure and uses of some ethers.
Ethers
General Formulas
Bent molecule
Central oxygen atom Hydrogen and alkyl group attached (R) or an aryl group (Ar)
Alcohols
R-O-H
Ar-OH Benzene ring with an OH R-O-R
Phenols
Ethers
Functional Groups
Properties of alcohols depend on the arrangement of the carbon atoms of the molecule Primary (1) carbon atom Secondary (2) carbon atom Tertiary (3) carbon atom
Primary Alcohol
RCH2OH
R2CHOH R3COH
Secondary Alcohol
Tertiary Alcohol
IUPAC Naming
Name the longest continous chain of carbons containing the OH group Number which carbon the OH is attached to End name in ol If more than one hydroxyl group, use suffixes diol, -triol, etc.
Replacement of hydrogen with a hydroxyl group greatly changes properties Not as homologous as alkanes Higher boiling points
Due to strong intermolecular attractions The more compact the molecule is, the more soluble it is 4-5 carbons or lesssoluble in water
Solubility
Hydration Reactions
Markovnikovs Rule
Production of alcohols
Methanol
1.7 billion gallons produced a year Used in formaldehyde, acetic acid, fuels (MTBE), silicones, refrigerants
Production of Alcohols
Ethanol
Its the alcohol thats found in those certain beverages that people shouldnt drink
Wines
12% ethanol
14-20% ethanol
Champagnes
Beers
4% ethanol
50% ethanol
Whiskey
Proof spirit: alcoholic content of a beverage, twice that of the alcohol content by volume (whiskey: 100 proof)
LD50 (Lethal dose to 50% of a population) Tested on animals Varies per species though See table 14.5
Methanol
Can cause permanent blindness or death in high amounts Vapors are very dangerous as well
Ethanol
Toxic to humans Acute poisoning kills several hundred a year (drinking contests) Long term poisioning
Isopropyl Alcohol
Rubbing alcohol Rapid evaporation Antiseptic More toxic than ethanol, but induces vomitting Used for the manufacture of acetone
Reactions
Occur on the functional groups May involve hydrogen atoms as well Dehydration Oxidation
Dehydration
Oxidation
Produces an aldehyde Then goes through further oxidation to produce a carboxylic acid Produces a ketone No reaction Cant break the carbon-carbon bond
Secondary
Tertiary
Oxidation Cont
More than one hydroxyl group Polyhydric groups Dihydric alcohols Trihydric alcohols
Glycols
Dihydric alcohols 1,2 ethanediol (ethylene glycol) HOCH2CH2OH Two hydroxyl groupsextensive intermolecular hydrogen bonding
Glycerol
Most important trihydric alcohol Syrupy liquid Nontoxic, product of the hydrolysis of fats and oils Nitroglycerin
Detonates on slight impact Reaction produces temps of 3000 C and pressures above 2000 atm
Phenols
Used as:
Antiseptic Disinfectants
Methyl derivatives
Cresols
Creosote
Phenols
Dihydroxybenzenes
Naming
Properties
Quite inert Although react violently in the air Low boiling pointsno hydrogen bonds Diethyl ether