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MCAT Organic > Alcohols > Flashcards

Alcohols Flashcards

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MCAT flashcards
1
Q

Suffix for alcohols

A

-ol

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2
Q

Prefix for alcohols

A

Hydroxy-

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3
Q

Phenol

A

Hydroxy attached to a benzene ring

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4
Q

Ortho

A

Next to the -OH on benzene ring

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5
Q

Meta

A

One down from -OH on benzene ring

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6
Q

Para

A

Directly across from -OH on benzene ring

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7
Q

Why are phenols so acidic?

A

Possible resonance between the ring & the lp’s on the oxygen make the H extra acidic

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8
Q

What causes alcohols to have high boiling & melting points?

A

Intermolecular hydrogen bonding

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9
Q

What does hydrogen bonding cause?

A

Increased melting points, boiling points, and solubility in water

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10
Q

What can cause an increase in boiling point?

A

Increased amount of -OH groups

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11
Q

Hydrogen bonding atoms

A

NOF

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12
Q

pKa of phenol

A

Around 10

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13
Q

Electron-withdrawing group on phenols?

A

Increase acidity

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14
Q

Electron-donating groups on phenols?

A

Decrease acidity

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15
Q

More alkyl groups creates?

A

Less acidity (donate electrons) & stabilizes positive charge stability, but destabilizes negative charge stability

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16
Q

What causes stability in carbocations?

A

More substitution

17
Q

What can primary alcohols be oxidized to ?

A

Aldehydes

18
Q

What can secondary alcohols be oxidized to?

A

Ketones

19
Q

What must primary alcohols be oxidized by to create aldehyde?

A

PCC

20
Q

Can tertiary alchohols be oxidized?

A

No

21
Q

What will oxidize a primary alcohol to a carboxylic acid?

A

Chromium

22
Q

What is Jones oxidation

A

CrO3, H2SO4 and acetone

23
Q

What will Jones oxidation do to primary & secondary alcohols

A

Primary- carboxylic acids

Secondary- ketones

24
Q

Mesylate

A

Contains -SO3CH3 from methanesulfonic acid
Better leaving group than hydroxyl
Protecting group

25
Q

Tosylate

A

Contain -SO3C6H4CH3
Better leaving group than hydroxyl
Protecting group

26
Q

Ketals & acetals are made from?

A

Diols

27
Q

How are ketals & acetals deprotected?

A

Aqueous acid

28
Q

Quinone

A

Treatment of phenols with oxidizing agents makes these (carbonyls on benzene ring)
Resonance stabilized electrophiles
Electron acceptors

29
Q

Phylloquinone is

A

Vitamin K used in photosynthesis & electron transport, carboxylation of some clotting factors in blood

30
Q

Hydroquinone

A

Benzene ring with 2 hydroxyl groups

31
Q

Hydroxyquinone

A

Contains 2 carbonyls and a variable number of hydroxyl groups on a benzene ring

32
Q

How do hydroxylquinones behave?

A

Like quinones with electron-donating groups making them less electronegative

33
Q

Ubiquinone/Coenzyme Q

A

Electron carrier associated with Complex I, II, and II of ETC
Reduced to ubiquinol when it accepts electrons
Within phospholipid bilayer

MCAT Organic (10 decks)

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