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Orgo II > C11: Alcohol Reactions > Flashcards

C11: Alcohol Reactions Flashcards

1
Q

oxidation of alkane to carboxylic acid

A

alkane – 1 alcohol – aldehyde – carboxylic acid

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2
Q

oxidation of alkane to ketone

A

alkane – 2ndary alcohol – ketone

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3
Q

R-OH –_____–> alkenes

A

dehydration

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4
Q

R-OH –_____–> ketones, aldhydes, acids

A

oxidation

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5
Q

R-OH –_____–> R-X (halides)

A

substitution

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6
Q

R-OH –_____–> R-H (alkanes)

A

reduction

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7
Q

R-OH –_____–> R-O-C(=O)-R’ (esters)

A

esterification

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8
Q

R-OH –_____–> R-OTs (tosylate esters)

A

tosylation

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9
Q

R-OH –______–>–______–> R-O-R’ (ethers)

A

[1] form alkoxide [2] R’X

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10
Q

___ and ____ ____ are easily oxided

A

Primary, Secondary, Alcohols

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11
Q

oxidation of ____ alcohols gives ketones

A

secondary

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12
Q

oxidation of ____ alcohols gives aldehydes

A

primary

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13
Q

______ can be further oxidized to carboxylic acid

A

aldhydes

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14
Q

Primary alcohol + ______ = carboxylic acid

A

Chromic acid

HO-(O=)Cr(=O)-OH

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15
Q

Primary alcohol + ______ = stop at aldehyde

A

PCC. HCl. (Pyridine or dichloromethane)

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16
Q

Collins Reagent

A

Chromium Trioxide + Pyridine

CrO3 + (benzene ring with N replacing one carbon)

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17
Q

Jones Reagent

A

Chromic acid + Hydrosulfuric acid + acetone

CrO3 + H2SO4 + CH3-C(=O)-CH3

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18
Q

Bleach

A

Sodium hypochlorite

NaOCl

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19
Q

DMSO4, Swerns Reagent

A

dimethyl sulfoxide, oxalyl chloride and triethyl amine

CH3-(S=O)C-CH3 , (COCl)2

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20
Q

Secondary Alcohol oxidized to ketone by

A

Chromium Reagent: Chromic acid or PCC

Non Chromium Reagent: Bleach, Swern, DMP

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21
Q

Primary Alcohol oxidized to aldehyde by

A

Chromium Reagent: PCC

Non Chromium Reagent: Swern or DMP

22
Q

Primary Alcohol oxidized to carboxylic acid by

A

Chromium Reagent: Chromic acid

Non Chromium Reagent: Bleach

23
Q

R-OH + TsOH

alcohol + p-toluenesulfonic acid

A 
R-O-Ts + H20
alkyl tosylate (p-toluenesulfonate ester) + water
24
Q

Primary alcohol + TsCl/pyridine –______—>

A

nucleophile: - (substitution, OH replaced by nucleophile)
base: - (elimination, C=C formed)

25
Q

____ displacement of tosylate ion, with inversion

A

SN2

26
Q

R-OTs + -OH —> ????

A

R-OH + -OTs

alcohol

27
Q

R-OTs + -C(triplebond)N —> ????

A

R-C(triplebond)N + -OTs

nitrile

28
Q

R-OTs + Br- —> ????

A

R-Br + -OTs

alkyl halide

29
Q

R-OTs + R’-O- —> ????

A

R-O-R’ + OTs

ether

30
Q

R-OTs + :NH3 —> ????

A

R-NH3+/-OTs

amine salt

31
Q

R-OTs + LiAlH4, LAH —> ????

A

R-H + -OTs

alkane

32
Q

Tertiary alcohol + HBr –____–> ????

A

SN1, carbocation formed

33
Q

Primary alcohol + HBr –____–> ????

A

SN2, no carbocation formed

34
Q

HCl + ZnCl2 , does what

A

Lucas Reagent, replaces OH

35
Q

___ and ____ alcohols react with Lucas reagent by SN1, a _____ reaction

A

secondary, tertiary, fast

36
Q

___ and ____ alcohols react with Lucas reagent by SN2, a _____ reaction

A

methyl and primary, slow

37
Q

Order of reactivity of alcohols with sulfuric acid

A

3>2>1

38
Q

Chromic acid test distinguishes ____ from ____ by ____

A

tertiary from secondary and primary by color, tertiary stays orange, secondary and primary turn blue green

39
Q

Lucas test distinguishes ___ from ___ by ____

A

Primary from secondary from tertiary by reaction rate
Primary - takes forever
Secondary - takes 1-5 min
Tertiary - takes less than a minute

40
Q

Best reagents for converting primary alcohol to alkyl halide

A

Chloride: SOCl2
Bromide: PBr3 or HBr
Iodide: I2

41
Q

Best reagents for converting secondary alcohol to alkyl halide

A

Chloride: SOCl2
Bromide: PBr3
Iodide: I2

42
Q

Best reagents for converting tertiary alcohol to alkyl halide

A

Chloride: HCl
Bromide: HBr
Iodide: HI

43
Q

acid dehydration of alcohol mechanism, works best with ____, follows _______ rule stating that the _____ substituted alkene will form

A

E1, tertiary and secondary, rearrangement may occur, Zaitsev rule, most

44
Q

H3C-H2C-OH —______—> CH2=CH2

A

H2SO4, heat

45
Q

H3C-H2C-OH —______—> H3C-H2C-O-CH2- _

A

H2SO4, no heat

46
Q

_____ migration after carbocation formation of a _____ forms a _____

A

methyl , pinacol, pinacolone

47
Q

alkene —______—> glycol —-______—> ketones and aldhydes

A

[1] OsO4/H202 [2] HIO4

48
Q

alcohol + nitric acid

R-OH + H-O-N(=O)-O-

A

alkyl nitrate ester + water

R-O-N(=O)-O-

49
Q

phosphoric acid + alcohol (up to x3)

A

[1] mono-R-phosphate
[2] di-R-phosphate
[3] tri-R-phosphate

50
Q

Williamson Ether Synthesis (step 1)

A

Alcohol + Na(NaH or K) —> R-O- +Na + H2

51
Q

Williamson Ether Synthesis (step 2)

A

alkoxide displaces the leaving group of a good SN2 substrate

R-O- + R’-CH2-X —> R-O-CH2-R’ + XNa

Orgo II (8 decks)

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