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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
carboxylic acid + carboxylic acid with acetic anhydride (CH3CO)2O and heat --->
anhydride
26
carboxylate + primary alkyl halide --->
ester
27
carboxylic acid + DCC, CH3OH --->
ester
28
ester reactivity and resonance
-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
29
alkyl halide + -CN -->
nitrile
30
synthesis: alkyl halide adding no carbons ---> carboxylic acid
primary: 1. NaOH 2. H2CrO4 secondary or tertiary: 1. NaOH 2.BH3, THF 3.H2O2, H2O, NaOH 4.H2CrO4
31
synthesis: alkyl halide adding 1 carbon ---> carboxylic acid
primary or secondary: 1. NaCN 2. H2O, HCl, heat OR 1. Mg, ether 2. CO2 3. HCl
32
synthesis: alkyl halide adding 2 carbons ---> carboxylic acid
1. Mg, ether (or Gilman) 2. epoxide 3. HCl 4. H2CrO4
33
anhydride + carboxylate --->
new anhydride + carboxylate
34
Grignard + formaldehyde with H3O+--->
primary alcohol
35
Grignard + aldehyde with H3O+ --->
secondary alcohol
36
Grignard + ketone with H3O+--->
tertiary alcohol
37
Grignard with H2O+ acid halide/ester --->
tertiary alcohol (2 identical substituents)
38
Gilman + acid halide -->
ketone
39
acetylide anion + aldehyde --->
alkynol
40
cyanide anion + aldehyde/ketone --->
cyanohydrin
41
acid halide + NaBH4 --->
primary alcohol
42
acid halide + 1. LATB-H -78C and 2.H2O -->
aldehyde
43
anhydride + NaBH4 --->
2 eq 1 alcohol
44
imine + NaBH4 / NaBH3CN / H2, Pd/C -->
primary or secondary amine
45
enamine + NaBH4 / NaBH3CN / H2, Pd/C -->
tertiary amine
46
aldehyde + NaBH4 / H2, Raney Ni -->
primary alcohol
47
ketone + NaBH4 / H2, Raney Ni -->
secondary alcohol
48
ester + LiAlH4 -->
primary alcohol
49
ester + DIBALH -->
aldehyde
50
carboxylic acid + LiAlH4 -->
primary alcohol
51
amide + LiAlH4 -->
amine
52
nitrile + NaBH4 / H2, Raney Ni -->
primary amine
53
reactivity: aldehydes and ketones
aldehyde>ketone>benzaldehyde>benzoketone EWG increase reactivity (example: CN) EDG decrease reactivity (example: OCH3)
54
Grignard + carboxylic acid -->
carboxylate (acid workup for carboxylic acid)
55
grignard + CO2 --->
carboxylate (acid workup for carboxylic acid)
56
protecting group alcohol
TMS-Cl or TBDMS-Cl with imidazole reverse with TBAF or H3O+
57
aldehyde/ketone + primary amine with trace H+ -->
imine
58
aldehyde/ketone + secondary amine with trace H+ -->
enamine
59
aldehyde/ketone + 1 eq alcohol with H+ --->
hemiacetal
60
aldehyde/ketone + 2 eq alcohol with H+ --->
acetal
61
aldehyde + peroxyacid(CF3CO3-) -->
carboxylic acid
62
ketone + peroxyacid (CF3CO3-) -->
ester
63
aldehyde/ketone + 2 eq thiol with H+ -->
thioacetal
64
thioacetal + H2, Raney Ni --->
alkane
65
aldehyde/ketone + wittig reagent --->
alkene
66
aldehyde/ketone protecting group
1 eq diol/H+ or 2 eq alcohol/H+ reversal = H3O+
67
carboxylic acid protecting group
1 eq alcohol/H+ reversal = HCl, H2O
68
hierarchy of migration for (CF3CO3-)
H > 3 > 2 > phenol > 1 > methyl
69
how to add carbons to thioacetal
1.nBuLi 2.CH3MgBr
70
how to cut of thioacetal to make alkane
H2, Raney Ni
71
primary alkyl halide + PPh3 + nBuLI -->
wittig reagent

o chem 2 (5 decks)

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