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MCAT Organic Chemistry > Chapter 5 : Alcohols > Flashcards

Chapter 5 : Alcohols Flashcards

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1
Q

what are alcohols

A

ROH ; suffix -ol ; prefix hydroxy-

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2
Q

what are phenols

A

benzene rings with hydroxyl groups

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3
Q

what is ortho position

A

adjacent carbons on ring

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4
Q

what is meta position

A

separated by one carbons on ring

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5
Q

what is para position

A

opposite sides of ring

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6
Q

how do hydrogen bonds affect alcohols

A

increase boiling and melting points; increase solubility

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7
Q

why are phenols more acidic than alcohols

A

ring can delocalize charge of conjugate base

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8
Q

how do electron donating groups affect alcohols (alkyl groups)

A

decrease acidity because they destabilize negative charge

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9
Q

how do electron withdrawing groups affect alcohols (electronegative atoms)

A

increase acidity because they stabilize negative charge

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10
Q

primary alcohol –> aldehyde

A

PCC ; weak oxidizing agent

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11
Q

primary alcohol –> carboxylic acid

A

CrO3 ; Na2Cr2O7 ; K2Cr2O7

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12
Q

secondary alcohol – > ketone

A

any oxidizing agent

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13
Q

How to make alcohols better LG from nucleophilic substitution reactions

A

conversion into mesylates or tosylates

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14
Q

what are mesylates

A

contain –SO3CH3 ; derived from methanesulfonic acid

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15
Q

what are tosylates

A

contain –SO3C6H4CH3 ; derived from toluenesulfonic acid

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16
Q

how do you protect aldehydes and ketones

A

conversion into acetals/ketals using two equivalents of alcohol (one equivalent = hemiacetal/ketal) or dialcohol

17
Q

how do you deprotect aldehydes and ketone

A

catalytic acid

18
Q

what are quinones

A

synthesized through oxidation of phenols ; resonance stabilized electrophiles

19
Q

what are biologically relevant quinones

A

vitamin K1 (phylloquinone) and vitamin K2 (menaquinone)

20
Q

what are hydroxyquinones

A

oxidation of quinonesw

21
Q

what is ubiquinone (coenzyme Q)

A

biologically active quinone that acts as an electron acceptor in complexes I, II, and III of the ETC ; reduced to ubiquinol

MCAT Organic Chemistry (12 decks)

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