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  • Alcohols, Phenols, and Ethers

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    This chapter covers alcohols, phenols, and ethers. It defines their general structures and functional groups. Alcohols are classified by whether they have a hydroxyl group on a primary, secondary, or tertiary carbon. Common alcohols like methanol and ethanol are produced industrially. Physiological effects range from toxicity to uses as disinfectants. Reactions include dehydration to form ethers or alkenes, and oxidation producing aldehydes, ketones, or no reaction. Multifunctional alcohols like glycols and glycerol are also discussed. Phenols are slightly acidic and used as antiseptics. Ethers are named based on groups

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    This chapter covers alcohols, phenols, and ethers. It defines their general structures and functional groups. Alcohols are classified by whether they have a hydroxyl group on a primary, secondary, or tertiary carbon. Common alcohols like methanol and ethanol are produced industrially. Physiological effects range from toxicity to uses as disinfectants. Reactions include dehydration to form ethers or alkenes, and oxidation producing aldehydes, ketones, or no reaction. Multifunctional alcohols like glycols and glycerol are also discussed. Phenols are slightly acidic and used as antiseptics. Ethers are named based on groups

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    303 views33 pages

    Alcohols, Phenols, and Ethers

    Uploaded by

    Kevin Thomas
    This chapter covers alcohols, phenols, and ethers. It defines their general structures and functional groups. Alcohols are classified by whether they have a hydroxyl group on a primary, secondary, or tertiary carbon. Common alcohols like methanol and ethanol are produced industrially. Physiological effects range from toxicity to uses as disinfectants. Reactions include dehydration to form ethers or alkenes, and oxidation producing aldehydes, ketones, or no reaction. Multifunctional alcohols like glycols and glycerol are also discussed. Phenols are slightly acidic and used as antiseptics. Ethers are named based on groups

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    Attribution Non-Commercial (BY-NC)
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    of 33

    Ch.

    14 Alcohols, Phenols, and Ethers

    Milbank High School

    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.

    Sec. 14.1 General Formulas and Functional Groups

    Two of the three families contain a hydroxyl group (OH)


    Alcohols Phenols Often made from alcohols and phenols

    Ethers

    All are considered organic derivatives of water.

    General Formulas

    Bent molecule

    Central oxygen atom Hydrogen and alkyl group attached (R) or an aryl group (Ar)

    General Formulas Cont

    Alcohols

    R-O-H
    Ar-OH Benzene ring with an OH R-O-R

    Phenols

    Ethers

    Functional Groups

    Group of atoms which confers characteristic properties on a family of organic compounds


    OH COOH Alkanes: none

    Sec. 14.2 Classification and Nomenclature of Alcohols

    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

    Classification and Nomenclature of Alcohols

    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.

    Physical Properties of Alcohols

    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

    Sec. 14.4 Preparation of Alcohols

    Hydration Reactions

    Markovnikovs Rule

    The hydroxyl group goes on the carbon with fewer hydrogens

    Production of alcohols

    Methanol

    1.7 billion gallons produced a year Used in formaldehyde, acetic acid, fuels (MTBE), silicones, refrigerants

    Production of Alcohols

    Ethanol

    Produced from sugars or starches by fermentation

    C6H10O5 C6H12O6 2CH3CH2OH + 2CO2 (Enzymes as catalysts)

    Its the alcohol thats found in those certain beverages that people shouldnt drink

    Production of Alcohols Cont

    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)

    Sec. 14.5 Physiological Effects of Alcohols

    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

    Most serious drug problem in US 40 times more addicts than heroin

    Isopropyl Alcohol

    Rubbing alcohol Rapid evaporation Antiseptic More toxic than ethanol, but induces vomitting Used for the manufacture of acetone

    Sec. 14.6 Chemical Properties of Alcohols

    Reactions

    Occur on the functional groups May involve hydrogen atoms as well Dehydration Oxidation

    Dehydration

    Removal of water Sulfuric acid as a catalyst Produces:


    Ether (excess ROH) + water Alkene (excess H2SO4) + water

    Oxidation

    Result depends on if alcohol is primary, secondary, or tertiary Primary


    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

    Sec. 14.7 Multifunctional Alcohols: Glycols and Glycerol

    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

    Higher boiling point Used as anti-freeze

    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

    Sec. 14.8 Phenols

    Slightly acidic Neutralized by strong bases

    Phenols

    Used as:

    Antiseptic Disinfectants

    First used was pure phenolproved to be too toxic

    Methyl derivatives

    Cresols

    Creosote

    Phenols

    Dihydroxybenzenes

    Components of biochemical molecules

    Sec. 14.9 Ethers

    Derivatives of water Both hydrogen atoms are replaced

    Naming

    Symmetrical Name groups attached and add ether

    Properties

    Quite inert Although react violently in the air Low boiling pointsno hydrogen bonds Diethyl ether

    Forms a peroxide in air First general anesthetic

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