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chapter 15 Flashcards

1
Q

reactivity scale

A

acid halide > anhydride > imine> enamine > aldehyde > ketone > carboxylic acid > ester > amide > nitrile > carboxylate

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2
Q

acid halide + carboxylate –>

A

anhydride

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3
Q

acid halide + H2O –>

A

carboxylic acid

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4
Q

acid halide + alcohol –>

A

ester

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5
Q

acid halide + 2 eq amine –>

A

amide

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6
Q

anhydride + H2O –>

A

2 carboxylic acids

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7
Q

anhydride + alcohol —>

A

ester + carboxylic acid

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8
Q

anhydride + 2 eq amine –>

A

amide + carboxylate (O- +NH3)

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9
Q

carboxylate + SOCl2 or PX3 with heat —>

A

acid halide

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10
Q

carboxylic acid + carboxylic acid with P2O5 or heat –>

A

anhydride

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11
Q

carboxylic acid + alcohol with HCl—>

A

ester + H2O
(Fischer esterification)

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12
Q

carboxylic acid + amine with heat (or DCC) —>

A

amide + H2O

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13
Q

ester + H2O with HCl –>

A

carboxylic acid + alcohol

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14
Q

ester + NaOH (hydroxide) with H2O —>

A

carboxylate + alcohol

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15
Q

ester + alcohol with HCl –>

A

new ester + alcohol

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16
Q

ester + alkoxide (CH3O-) with alcohol —>

A

ester + alcohol

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17
Q

ester + amine —>

A

amide + alcohol

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18
Q

amide + H2O with HCl, heat—>

A

carboxylic acid + protonated amine

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19
Q

amide + NaOH (hydroxide) with H2O, heat —>

A

carboxylate + amine

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20
Q

amide + alcohol with HCl, heat —>

A

ester

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21
Q

amide + SOCl2 —>

A

nitrile

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22
Q

pthalamide + 1.NaOH, 2.CH3CH2Br, 3.HCl,H2O,heat, 4.NaOH —>

pthalamide = anhydride with N instead of O in ring

A

primary amine + two carboxylates

Gabriel’s amine synthesis
second step determines amine being formed

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23
Q

nitrile + H2O with HCl, heat —>

A

carboxylic acid

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24
Q

carboxylic acid + PX3, pyridine, heat —>
carboxylic acid + SOCl2, pyridine, heat —>

A

acid halide

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25
Q

carboxylic acid + carboxylic acid with acetic anhydride (CH3CO)2O and heat —>

A

anhydride

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26
Q

carboxylate + primary alkyl halide —>

A

ester

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27
Q

carboxylic acid + DCC, CH3OH —>

A

ester

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28
Q

ester reactivity and resonance

A

-more stable leaving group of an ester is, the more reactive it will be
-if leaving group can resonate = ester more reactive
-benzene rings: EWG = more reactive ester and EDG = less reactive ester

examples: EWG = NO2 and EDG = OCH3

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29
Q

alkyl halide + -CN –>

30
Q

synthesis: alkyl halide adding no carbons —> carboxylic acid

A

primary:
1. NaOH
2. H2CrO4

secondary or tertiary:
1. NaOH
2.BH3, THF
3.H2O2, H2O, NaOH
4.H2CrO4

31
Q

synthesis: alkyl halide adding 1 carbon —> carboxylic acid

A

primary or secondary:
1. NaCN
2. H2O, HCl, heat

OR

  1. Mg, ether
  2. CO2
  3. HCl
32
Q

synthesis: alkyl halide adding 2 carbons —> carboxylic acid

A
  1. Mg, ether (or Gilman)
  2. epoxide
  3. HCl
  4. H2CrO4
33
Q

anhydride + carboxylate —>

A

new anhydride + carboxylate

34
Q

Grignard + formaldehyde with H3O+—>

A

primary alcohol

35
Q

Grignard + aldehyde with H3O+ —>

A

secondary alcohol

36
Q

Grignard + ketone with H3O+—>

A

tertiary alcohol

37
Q

Grignard with H2O+ acid halide/ester —>

A

tertiary alcohol (2 identical substituents)

38
Q

Gilman + acid halide –>

39
Q

acetylide anion + aldehyde —>

40
Q

cyanide anion + aldehyde/ketone —>

A

cyanohydrin

41
Q

acid halide + NaBH4 —>

A

primary alcohol

42
Q

acid halide + 1. LATB-H -78C and 2.H2O –>

43
Q

anhydride + NaBH4 —>

A

2 eq 1 alcohol

44
Q

imine + NaBH4 / NaBH3CN / H2, Pd/C –>

A

primary or secondary amine

45
Q

enamine + NaBH4 / NaBH3CN / H2, Pd/C –>

A

tertiary amine

46
Q

aldehyde + NaBH4 / H2, Raney Ni –>

A

primary alcohol

47
Q

ketone + NaBH4 / H2, Raney Ni –>

A

secondary alcohol

48
Q

ester + LiAlH4 –>

A

primary alcohol

49
Q

ester + DIBALH –>

50
Q

carboxylic acid + LiAlH4 –>

A

primary alcohol

51
Q

amide + LiAlH4 –>

52
Q

nitrile + NaBH4 / H2, Raney Ni –>

A

primary amine

53
Q

reactivity: aldehydes and ketones

A

aldehyde>ketone>benzaldehyde>benzoketone

EWG increase reactivity (example: CN)
EDG decrease reactivity (example: OCH3)

54
Q

Grignard + carboxylic acid –>

A

carboxylate
(acid workup for carboxylic acid)

55
Q

grignard + CO2 —>

A

carboxylate
(acid workup for carboxylic acid)

56
Q

protecting group alcohol

A

TMS-Cl or TBDMS-Cl with imidazole

reverse with TBAF or H3O+

57
Q

aldehyde/ketone + primary amine with trace H+ –>

58
Q

aldehyde/ketone + secondary amine with trace H+ –>

59
Q

aldehyde/ketone + 1 eq alcohol with H+ —>

A

hemiacetal

60
Q

aldehyde/ketone + 2 eq alcohol with H+ —>

61
Q

aldehyde + peroxyacid(CF3CO3-) –>

A

carboxylic acid

62
Q

ketone + peroxyacid (CF3CO3-) –>

63
Q

aldehyde/ketone + 2 eq thiol with H+ –>

A

thioacetal

64
Q

thioacetal + H2, Raney Ni —>

65
Q

aldehyde/ketone + wittig reagent —>

66
Q

aldehyde/ketone protecting group

A

1 eq diol/H+ or 2 eq alcohol/H+

reversal = H3O+

67
Q

carboxylic acid protecting group

A

1 eq alcohol/H+

reversal = HCl, H2O

68
Q

hierarchy of migration for (CF3CO3-)

A

H > 3 > 2 > phenol > 1 > methyl

69
Q

how to add carbons to thioacetal

A

1.nBuLi
2.CH3MgBr

70
Q

how to cut of thioacetal to make alkane

A

H2, Raney Ni

71
Q

primary alkyl halide + PPh3 + nBuLI –>

A

wittig reagent

o chem 2 (5 decks)

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