Alcohols Flashcards

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1
Q

phenol

A

when there is a hydroxide group attached to an aromatic ring

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2
Q

positions relative to the main functional group

A

ortho-, meta-, para-

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3
Q

physical properties of alcohols

A
  • intermolecular H-bonding
  • higher mp
  • higher bp
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4
Q

phenols are ____ acidic relative to nonaromatic alcohols.

A
  • much more (resonance stabilization of neg charge)
  • form salts with inorganic bases such as NaOH
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5
Q

The hydroxyl hydrogen is…

A

weakly acidic

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6
Q

alkyl groups…

A

donate electrons and decrease acidity

more substituted carbocations are more stable

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7
Q

1° alcohol ~~PCC~~>

A

aldehyde

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8
Q

2° alcohol ~~Na2Cr2O7, H2SO4~~>

A

ketone

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9
Q

1° alcohol ~~Na2Cr2O7, H2SO4~~>

A

CA

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10
Q

1° alcohol ~~CrO3, H2SO4, acetone~~>

A

CA

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11
Q

2° alcohol ~~CrO3, H2SO4, acetone~~>

A

ketones

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12
Q

mesylates and tosylates

A
  • OH groups are poor LG for nucleophilic sub reactions
  • can be reacted to form these
  • also protecting reagents
  • SO3CH3 and SO3C6H4CH3 respectively
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13
Q

aldehydes and ketones can be reacted w two equivalents of an alcohol or a diol forming…

A

acetals and ketals

protect from LiAlH4 and other reducing agents

freed using H2O and H+

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14
Q

treatment of phenols w oxidizing agents produces compounds called…

A

quinones

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15
Q

due to the conjugated ring system, quinones are…

A

resonance-stabilized electrophiles

not necessarily aromatic

e- receptors in ETC and in photosynthesis and aerobic respiration

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16
Q

phylloquinone

A

Vitamin K1

photosynthesis and carboxylation of clotting factors

17
Q

menaquinones

A

Vitamin K2

18
Q

hydroxyquinone

A

oxidized phyllo- and menaquinones

extra hydroxyl group

biologically active

behave like quinones w EDGs, making these slightly less electrophilic

19
Q

ubiquinone

A

biologically active quinone

coenzyme Q

electron carrier associated with complexes I-III of ETC

can be reduced to ubiquinol

lipid soluble