Alcohols
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General Formula
R-OH
Nomenclature IUPAC
-e of alkane root is changed to -ol
Nomenclature Common Name
name alkyl group as a derivative and followed by alcohol ex: ethyl alcohol
When alcohol is NOT the highest prority group, it is named as a substituent with the prefix ____
hydroxy-
Phenols
hydroxyl groups attached to aromatic rings the hydroxyl H is particularly acidic due to the resonance
When benzene rings contain two substituents, two groups on ADJACENT carbons are called ________ and two groups SEPERATED by a carbon are called ______. Two groups on OPPOSITE sides of the ring are called _____
ortho meta para
One of the prominent properties of alcohols is that tey are capable of _________ which results in higher melting and boiling points. Molecules with more than one hydroxyl group show greater degrees of ______
hydrogen bonding hydrogen bonding
Hydrogen Bond
induction from oxygen pulls electrons away from hydrogen to make + charge on H and - charge on O which then leads to a noncovalent bond between the H and O.
Strong acids have high ____ values and low ____ values meaning that _____ are the most acidic alcohols. This is because of the _______ , the negative charge on the oxygen is stabilized to create an anion like environment.
Ka pKa phenols resonance stabilization
The presence of other substituents on the ring effect the ____, ____ and _______. Electron withdrawing groups ____ acidity while electron donating groups _____ acidity.
acidity, boiling point, melting point increase decrease
The presence of more alkyl groups in non aromatic alcohols produce _____ acidic molecules as the alkyl groups _____ electron density and ____ the negative charge. Conversely, they ____ positive charge explaining why more substituted carbocations have higher stability than less substituted carbocations.
less increase destabilize stabilize
PCC
anhydrous oxidant oxidizes Primary Alcohols into Aldehydes oxidized Secondary Alcohols to Ketones does this as it lacks the water needed to hydrate the aldehyde
With other oxidizing agents, aldehydes are hydrated to form ______ whcih can then be oxidized to ____
geminal diols carboxylic acids
Tertiary alcohols cannot be oxidized because they are already as oxidized as they can be without ______
breaking a C-C bond
Sodium/Potassium Dichromate Salts
strong oxidizing agent Primary Alcohol goes to Carboxylic Acid Secondary Alcohol to Ketone
Jones Oxidation
Chromium Trioxide in Sulfuric Acid and Acetone, strongest oxidation Primary Alcohols to Carboxylic Acids Secondary Alcohols to Ketones
Hydroxyl groups of alxohols are ____ leaving groups
poor
Mesylate
compound with the functional group SO3CH3 derived from methansulfonic acid alcohol + base + methylsulfonyl chloride
Tosylate
compound with the functional group -SO3C6H4CH3 derived from toluenesulfonic acid to produce an ester alcohol + p-toluenesulfonyl chloride
Mesyl and TOsyl groups make the hydroxyl of an alcohol a ______ leaving group and serve as ____ groups.
better protecting
Acetal
formed as a protecting group between an aldehyde/ketone with either: 1) two equivalents of alchol 2) a diol Primary Carbons with 2 OR groups and a Hydrogen do not react with reducing agents like LiAlH4 to protect the aldehyde/ketone until deprotection
Ketals
formed as a protecting group between an aldehyde/ketone with either: 1) two equivalents of alchol 2) a diol Secondary Carbons with 2 OR groups do not react with reducing agents like LiAlH4 to protect the aldehyde/ketone until deprotection
Quinone
phenols treated with oxidizing agents the OH becomes a carbonyl named by indicating position of carbonyls numerically and adding the name quinone to the parent phenol not necessarily always aromatic serve as electron acceptors
Phylloquinone
vitamin K1 important in photosynthesis and carboxylation of clotting factors