Alcohols Flashcards
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
Hydroxyquinones
share the same ring and carbonyl backbone as quinone but have one or multiple hydroxyls added
behave like quinones with electron donating groups making them slightly less electrophillic
named by numbering position of hydroxyl group, total number of hydroxyls in prefic and the substituent name hydroxy
Ubiquinone
coenzyme Q
biologically active quinone
electron carrier most oxidized form and reduced to uniquinol when accepting electrons
long alkyl chain allows it to be lipid soluble
