MCAT Organic Chemistry Chapter 5- Alcohols

Alcohols

-have general form ROH
-named with suffix -ol
-if not highest priority, given prefix hydroxy-

Phenols

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Hydrogen bondings effect on alcohols

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Why are phenols more acidic than other alcohols?

because the aromatic ring can delocalized the charge of the conjugate base

Electron-donating groups like alkyl groups...

decrease acidity because they destabilize negative charges

Electron-withdrawing groups, such as EN atoms and aromatic rings...

increase acidity because they stabilize negative charges

How to oxidize primary alcohols to aldehydes?

react them with PCC

How to oxidize primary alcohols to carboxylic acids?

react them with strong oxidizing agent like chromium

Purpose of converting alcohol to mesylates or tosylates?

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Mesylates

contain functional group -SO3CH3, which is derived from methanesulfonic acid

Tosylates

contain the functional group -SO3C6H4CH3, which is derived from toluenesulfonic acid

How alcohols act as protecting groups

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Deprotection

acetal or ketal can be converted back to a carbonyl by catalytic aqueous acid

Quinone

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Phylloquinone

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Menaquinones

vitamin K2

Hydroxyquinones

produced by oxidation of quinones, adding a variable number of hydroxyl groups

Ubiquinone

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What chemical properties of ubiquinone allow it to carry out its biological functions?

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