Alcohols, Diols, Thiols Flashcards
What are alcohols ?
Organic compounds containing hydroxyl groups
What is the most common and useful compound in nature, in industry, and around the house ?
Alcohol
Ethyl alcohol was considered to be what?
The essence of wine
Where is ethyl alcohol found in?
Alcoholic beverages, cosmetics, and drug preparations
What is methyl alcohol used as ?
A fuel and solvent
What is isopropyl alcohol use for ?
As a skin cleanser for injections and minor cuts
What are alcohols with two OH groups called ?
Diols or glycols
What does the term glycol generally mean ?
1,2 - diol or vicinal diol
How are glycols usually synthesized ?
By the hydroxylation of alkenes, using peroxyacids, osmium tetroxide, or potassium permanganate
What are phenols ?
Compounds in which an OH group is directly attached to an aromatic ring
How do phenols differ from alcohols ?
Phenols are more acidic in water
What alcohols are liquid at room temperature ?
11 to 12 carbon atoms
Which alcohols are heavier but still fruity odors ?
Higher alcohols
What are the two important intermolecular forces es responsible for the boiling point of alcohols ?
Hydrogen bonding
Dipole-dipole attractions
Which is the major intermolecular attraction responsible for ethanols high boiling point ?
Hydrogen bonding
Dipole-dipole attractions also contribute to what ?
To the relatively high boiling points of alcohols and ethers
Explain the solubility of alcohols in water
Alcohols form hydrogen bonds with water, and several of the lower-molecular-weight alcohols are miscible with water
When does the water solubility of alcohol decrease?
When the alkyl group becomes larger
What is the use of methanol ?
Industrial solvent
Preparation of methyl ethers, methyl esters and other compounds used in plastic, medicine, fuels and solvents
Why is methanol most common industrial solvent ?
Cheap
Relatively less toxic
Dissolves a wide variety of polar and non polar substances
What is ethanol used for ?
Excellent solvent of low toxicity that is cheap to produce
Good motor fuel
Ingredient in many mouthwashes
What are both ethanol and propane-2-ol used for?
Topical antiseptic
How is alkoxide ion formed ?
By removing the hydroxyl proton from alcohol by reduction with active metal such as sodium or potassium
The reactivity of alcohols towards sodium and potassium decreases in what order ?
Methyl
Primary
Secondary
Tertiary
Sodium reacts quickly with what ?
Primary alcohols and some secondary alcohols
What reacts quickly with tertiary alcohols and some secondary?
Potassium, as it is more reactive than sodium
What is more acidic phenol or cyclohexanol ?
Phenol
Why is phenol acidic ?
What was phenol once called “
Carbolic acid because of its stability to neutralize common bases
What is phenol used as ?
Antiseptic agent
What are grignards reagents ?
Strong nucleophiles and strong bases
What is the most useful nucleophilic reaction of Grignard reagents ?
Additions to carbonyl groups
Grignards reagents first adds to what ?
Ketones, aldehydes, formaldehyde to form an alkoxide ion
How is alkoxide ion turned into alcohol ?
Additional of dilute acid
How is primary alcohol formed ?
By addition of Grignard reagent to a formaldehyde, followed by protonation
Formation of primary alcohols
How are secondary alcohols formed ?
By addition of Grignard reagent to an aldehyde in ether, followed by protonation
Formation of secondary alcohols
How are tertiary alcohols formed ?
By addition of Grignard reagent to ketones, followed by protonation
Formation of tertiary alcohol
Oxidation of primary alcohols leads to what ?
Aldehyde and further oxidation leads to acid
Secondary alcohols are oxidized to what ?
Ketones
Tertiary alcohols are oxidized to what “
They can’t be oxidized
Oxidation of primary alcohols
What acid is used for oxidation if secondary alcohols ?
Chromic acid reagent
Oxidation of secondary alcohols
Why are tertiary alcohols resistant to oxidation ?
Tertiary alcohols don’t have hydrogen atoms so a carbon-carbon bond needs to be broken which requires severe conditions
Alcohols are reduced to what ?
Alkanes
Why is reduction of alcohols rare?
Because it removes a functional group, leaving fewer options for further reactions
What are the steps to reduce alcohol ?
By dehydration to an Alkene, then hydrogenating the Alkene
Reduction of alcohols
What is bimolecular dehydration of alcohols?
Type of condensation that joins two or more molecules often with the loss of a small molecule like water
What is bimolecular dehydration of alcohol used for ?
For the industrial synthesis of diethyl ether and dimethyl ether
What are the two reactions included in bimolecular dehydration ?
Elimination, substitution
How to get a carboxylic ester ?
Replacing the OH group of a carboxylic acid with the OR group of an alcohol
Fischer esterification
What is the application of ester as drugs ?
What is the application of alcohols in metabolism of drugs ?
