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Chem GRE > Organic Rxns > Flashcards

Organic Rxns Flashcards

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1
Q

Alkane + X2

with heat or light

A

Alkyl halide + acid

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2
Q

Alkene

with H2 and Pt/Pd/Ni

A

Alkane

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3
Q

Acid + alcohol

with acid catalyst

A

Ester + water

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4
Q

Isobutane + Br2

with heat or light

A

t-butyl bromide

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5
Q

Alkene + HX

A

Mono-subst. alkyl halide

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6
Q

Alkene + X2

A

Di-subst. alkyl halide

Subst. on different C’s

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7
Q

Alkyne + 2HX

A

Di-subst. alkyl halide

Subst. on the same C

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8
Q

Alkyne + 2X2

A

Tetra-subst. alkyl halide

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9
Q

Allylic alkene

with NBS, light

A

Allylic bromide

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10
Q

Alcohol + HX, PX3, etc.

A

R-X

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11
Q

R-X

with I-

A

R-I + X-

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12
Q

Unhindered substrate

with strong nucleophile

A

Sn2: Substitution with reversed chirality

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13
Q

Carbocation-forming substrate

with weak nucleophile, stable LG (WB)

A

Sn1: Substitution with mixed chirality (sometimes rearrangements)

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14
Q

Carbocation-forming substrate

with good ionizing solvent

A

E1: Zaitsev (MS) product (sometimes rearrangements)

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15
Q

Anti-coplanar arrangement

with strong base

A

E2: Zaitsev (MS) product (cis or trans based on substrate)

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16
Q

R-X + HO-

A

Sn: R-OH + X-

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17
Q

R-X

with R’O or R’S

A

Sn: Williamson ether synthesis: R-O-R or R-S-R

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18
Q

R-X

with excess :NH3

A

Sn: R-NH2 + NH4X

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19
Q

R-X

with -CN

A

Sn: R-CN + X-

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20
Q

R-C(trip)C-

with R’-X

A

Sn: R-C(trip)C-R’ + X-

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21
Q

H-CR2-CR2-X

with KOH

A

E: R2C=CR2 + X-

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22
Q

Br-CR2-CR2-BR

with KI

A

R2C=CR2 + I-Br + KBr

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23
Q

R-X (not F) + Mg

in diethyl ether

A

Grignard: R-Mg-X

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24
Q

R-X (not F) + 2Li

A

Organolithium: R-Li + LiX

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25
Q

R-X

(1) Mg or Li
(2) H2O

A

Reduction: R-H

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26
Q

Vicinal dibromide

with NaI in acetone

A

E2: Alkene

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27
Q

Alcohol

with strong acid catalyst and heat

A

E1: Zaitsev alkene

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28
Q

Long chain alkane

with heat, catalyst

A

Catalytic cracking: alkanes and alkenes

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29
Q

Alkane

with heat, catalyst

A

Alkene + H2

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30
Q

Alkyl halide

with base, heat

A

Alkene + HX

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31
Q

C-C-N-(CH3)3

with Ag2O, heat

A

Hoffmann/Cope elimination: Hoffman alkene + :N(CH3)3

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32
Q

Alkyne

H2, Pd/BaSO4 in quinoline

A

Reduction: cis alkene

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33
Q

Alkyne

with Na, NH3

A

Reduction: trans alkene

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34
Q

R’-C=O-R

with Ph3P=CHR’’

A

Wittig: R’C=CHR’‘-R + Ph3P=O

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35
Q

Alkene

with water and acid

A

Alcohol

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36
Q

Alkene

with X2

A

Oxidation: Vicinal dihalide

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37
Q

Alkene

with HOX

A

Oxidation: Neighboring halo/alcohol

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38
Q

Alkene

with HOOH

A

Oxidation: Vicinal diol

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39
Q

Alkene

with HX

A

Alkyl halide

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40
Q

Alkene

with O2

A

Oxidative cleavage: 2 carbonyls

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41
Q

Alkene

with O

A

Epoxidation: CCO triangle

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42
Q

Alkene

with CH2

A

Cyclopropane

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43
Q

Alkene

with HBr, HOOH, heat

A

Anti-Markovnikov (LS) bromination product

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44
Q

Alkene
with Hg(OAc)2, water
then NaBH4

A

Oxymercuration/demercuration: Markovnikov alcohol

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45
Q

Alkene
with BH3+THF
then HOOH, -OH

A

Hydroboration: Anti-Markovnikov alcohol

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46
Q

Alkene

with X2

A

Anti alkyl halide

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47
Q

Alkene

with X2 in water

A

Anti halohydrin (Markovnikov)

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48
Q

Diazomethane

with heat/UV

A

Carbene formation: H-:C-H (methylene)

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49
Q

Halogenated molecule

with base

A

Halogenated carbene

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50
Q

Epoxide

with strong acid

A

Epoxide opening: anti 1,2-diol (glycol)

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51
Q

Alkene

with OsO4 + H2O2

A

Syn dihydroxylation: syn 1,2-diol

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52
Q

Alkene

with KMnO4 + base

A

Syn dihydroxylation: syn 1,2-diol

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53
Q

Alkene

with conc. KMnO4

A

Oxidative cleavage: Acids and maybe CO2

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54
Q

Alkene

O3, then Zn or dimethyl sulfide

A

Oxidative cleavage: Ketones and aldehydes

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55
Q

Alkene

with BF3

A

Cationic polymerization: Addition polymer

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56
Q

Alkenes

with metal catalyst

A

Olefin metathesis: new alkenes

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57
Q

2 methanes

Heat

A

Acetylene + 3H2

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58
Q

Acetylide + R-X

A

Sn2: R-C(3)C-R’ + X-

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59
Q

Acetylide + carbonyl

A

Sn: R-C(3)-OH

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60
Q

Vicinal or geminal dihalide

with VERY strong base

A

Alkyne + 2HX

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61
Q

Alkyne

with H2 and Pt/Pd/Ni

A

Alkane

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62
Q

Alkyne

with Lindlar’s (Pd) catalyst

A

cis alkene

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63
Q

Alkyne

with e- from Na in liquid NH3

A

trans alkene

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64
Q

Alkyne + X2

A

cis and trans alkenes

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65
Q

Alkyne + HX

A

Markovnikov alkene –> geminal alkyl dihalide

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66
Q

Alkyne + HX + ROOR

A

Antimarkovnikov alkene

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67
Q 
Alkyne
with Hg(II) then acid
A

Enol –> ketone

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68
Q

Alkyne

with Sia2BH then HOOH

A

Antimarkovnikov enol –> ketone or aldehyde

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69
Q

Alkyne

with cold, dilute KMnO4

A

alpha-ketones (vicinal carbonyls)

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70
Q

Terminal alkyne

with cold, dilute KMnO4

A

ketone + neighboring COOH

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71
Q

Alkyne

with hot KMnO4

A

carboxylic acids

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72
Q

Terminal alkyne

with hot KMnO4

A

carboxylic acid + CO2 gas

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73
Q

Alkyne

with ozone

A

carboxylic acids

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74
Q

CO + 2H

with catalyst in hi T, hi P

A

Methanol

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75
Q

Glucose

with yeast enzymes

A

Fermentation: Ethanol + 2CO2

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76
Q

Ethene and water

with catalyst in hi T, hi P

A

Ethanol

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77
Q

Propylene and water

with catalyst in hi T, hi P

A

Propan-2-ol

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78
Q

Alcohol

with Na or K in NaH

A

Alkoxide and H gas

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79
Q

Terminal alkyne

with NaNH2

A

Sodium acetylide + NH3

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80
Q

Formaldehyde

with OMR

A

Primary alcohol

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81
Q

Aldehyde

with OMR

A

Secondary alcohol

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82
Q

Ketone

with OMR

A

Tertiary alcohol

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83
Q

Acid chloride or ester

with 2 OMR

A

Tertiary alcohol (with two R1’s)

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84
Q 
Ethylene oxide (CCO triangle)
with OMR
A

Primary alcohol

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85
Q

Water

with OMR

A

R-H and LiOH/XMgOH

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86
Q

Ketone or aldehyde

with NaBH4 or LAH

A

Secondary or primary alcohol (need to use NaBH4 to preserve acids or esters)

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87
Q

Carbonyl

with H2 and Raney Ni

A

Alcohol

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88
Q

NaHS

with unhindered R-X

A

R-SH (thiol) + NaX

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89
Q

Pri/sec alcohol

with chromic acid

A

Carboxylic acid/ ketone

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90
Q

Pri/sec alcohol

with PCC in CH2Cl2

A

Aldehyde/ ketone

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91
Q

Collins reagent

A

PCC

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92
Q

Jones reagent

A

Chromic acid

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93
Q

Pri/sec alcohol

with nitric acid

A

Carboxylic acid/ ketone

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94
Q

Pri/sec alcohol

with KMnO4

A

Carboxylic acid/ ketone

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95
Q 
Pri/sec alcohol
with Swern (DMSO)
A

Aldehyde/ ketone

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96
Q 
Pri/sec alcohol
with DMP (iodine)
A

Aldehyde/ ketone

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97
Q

Pri/sec alcohol

with NaOCl

A

Carboxylic acid/ ketone

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98
Q

Alcohol

with TsCl in pyridine

A

Tosylate ester

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99
Q

Alcohol

1) TsCl in pyridine
(2) LAH/NaBH4 (X-

A

Alkane (alkyl halide)

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100
Q

Alcohol

with HX

A

Alkyl halide (rearr.)

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101
Q

3/2/1 alcohol

with HBr in water

A

Sn1/1/2: Alkyl bromide (rearr.)

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102
Q

3/2 alcohol

with Lucas reagent (HCl and ZnCl2)

A

Fast Sn1: Alkyl chloride (rearr.)

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103
Q

Primary alcohol

with Lucas reagent (HCl and ZnCl2)

A

Slow Sn2 Alkyl chloride

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104
Q

1/2 Alcohol

with PXn or P/I2

A

Alkyl halide (NO rearr.)

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105
Q

Alcohol

with SOCl2

A

Alkyl halide + SO2 + HCl (g’s)

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106
Q

1/2 alcohols to alkyl chlorides

A

SOCl2

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107
Q

Tertiary alcohols to alkyl halides

A

HX

108
Q

1/2 alcohols to alkyl bromides

A

PBr3

109
Q

1/2 alcohols to alkyl iodide

A

P/I2

110
Q

Alcohol

with acid catalyst

A

E1: Alkene (rearr.)

111
Q

Alcohol
with acid
(Subst. reaction)

A

Ether

112
Q

Diol

with acid

A

Pinacol rearrangement: ketone

113
Q

1,2-diol

with periodic acid

A

Ketones and aldehydes (like ozone)

114
Q

Alcohol

with acid

A

Ester and water

115
Q

Alcohol

with acid halide

A

Ester and HX

116
Q

Alkoxide

with unhindered R’X

A

Williamson Ether Synthesis: R-O-R’ + X-

117
Q

R-OH

with Na/K/NaH then R’-X

A

Williamson Ether Synthesis: R-O-R’ + X-

118
Q

Alkene
with ROH and Hg(OAc)2
then NaBH4

A

Ether

119
Q

2 primary R-OH

with H+

A

R-O-R

120
Q

R-O-R’

with excess HX (Br, I)

A

R-X + R’-X (or phenol)

121
Q

Ether

with O2

A

Hydroperoxide + dialkyl peroxide

122
Q

Thiol

with -OH

A

Thiolate ion

123
Q

Sulfide

witih HOOH in acetic acid

A

Sulfoxide then sulfone

124
Q 
Alkene
with peroxyacid (MCPBA or MMPP)
A

Epoxide + acid

Alkene stereochem retained

125
Q

Alkene

X2 in H2O

A

Markovnikov halohydrin

attack on MS carbon

126
Q

Halohydrin

with base

A

Epoxide (or cyclic ether) + X-

127
Q

Epoxide

with aqueous acid

A

Sn2: anti glycol

attack MS carbon

128
Q

Alkene

with aqueous peroxyacid

A

Glycol

129
Q

Epoxide

with alcohol

A

Sn2: anti alkoxy alcohol

130
Q

Epoxide

with HX

A

Halohydrin, then vicinal dihalide

131
Q

Epoxide

with -OH

A

Sn2: Anti glycol

attack unhindered C

132
Q

Epoxide

with alkoxide

A

Sn2: anti alkoxy alcohol

133
Q

Epoxide

with amine

A

Sn2: anti alcohol amine

134
Q

Epoxide

with OMR

A

Alcohol; least hindered C is attacked

135
Q

Conjugated diene

with HX

A

1,2 and 1,4 addition products (Markovnikov)

136
Q

Alkene

with conc. Br2

A

Saturated vicinal dibromide

137
Q

Alkene

with trace NBS, light

A

Allylic bromide

138
Q

Diene

with electron-poor alkene

A

Diels-Alder: Cyclohexene ring

139
Q

Diene

with electron-poor alkyne

A

Diels Alder: Cyclohexa-1,4-diene ring

140
Q

Benzene

with KMnO4

A

NR

141
Q

Benzene

with Br2 in CCl4

A

NR

142
Q

Benzene

with Br2 and FeBr3

A

Ph-Br

143
Q

Reagent to brominate benzene?

A

FeBr3

144
Q

Reagent to chlorinate benzene?

A

AlCl3

145
Q

Reagent to iodinate benzene?

A

I2 and HNO3

146
Q

Benzene

with HNO3 in H2SO4

A

Ph-NO2 via NO2+

147
Q

Ph-NO2

with Zn, Sn, or Fe in HCl

A

Ph-NH2

148
Q

Benzene

with SO3 in H2SO4

A

Ph-SO2OH

149
Q

Water

with SO3

A

H2SO4

150
Q

Ph-SO3H

with water

A

Benzene + H2SO4

151
Q

Benzene

with R-X (+ Lewis acid catalyst)

A

Friedel-Crafts: Ph-R + H-X

often polyalkylation

152
Q

Alkene

with HF

A

Carbocation

153
Q

Alcohol

with BF3

A

Carbocation (no O)

154
Q 
Benzene
with acyl (acid) halide
A

Ph-C(=O)-R (monosubst.)

155
Q

Reagent to get acylated product to alkylated product?

A

Zn(Hg) in aqueous HCl

156
Q

Benzene

with CO, HCl, CuCl, AlCl3

A

Gatterman-Koch: Aryl aldehydes

157
Q

EWG-Aryl

with Nuc

A

Ortho/para substitution

158
Q

Aromatic ring

with strong base, hi T

A

Substitution via benzyne

159
Q

4 pi donors (EAS)

A

NH2, OH, OR, NCHOCH3
O/P Directing
Activating

160
Q

2 sigma donors (EAS)

A

R, Ph
O/P Directing
Activating

161
Q

Halogens are… (EAS)

A

O/P Directing

Deactivating

162
Q

4 Carbonyls (EAS)

A

Ketone, acid, aldehyde, ester
Meta directors
Deactivating

163
Q

4 strong electrophiles (EAS)

A

SO3H, C(trip)N, NO2, N+R3
Meta directors
Deactivating

164
Q

2 R-Li

with CuI

A

R2CuLi + LiI

165
Q

R’-X

with R2CuLi

A

R’-R + R-Cu + LiX

166
Q

R-X + Alkene-R’

with Pd catalyst, base

A

Heck reaction:
R-C=C-R’ at LS end
usually trans

167
Q

Aryl/vinyl-X + boron reagent

with Pd catalyst, base

A

Suzuki coupling:

R-R’, stereochem of reagent is preserved

168
Q 
Alkene/alkyne
with B(OR)2
A

Alkane/alkene with B(OR)2 at LS end

169
Q

Benzene

with Na or Li in liq NH3 with ROH

A

Birch reduction:
cyclohexa-1,4-diene
via radical

170
Q

Phenol

with chromic acid

A

QUinone: 1,4-diketone

171
Q

Phenol

with CO2

A

Salicylic acid (1,2 acid alcohol on ring)

172
Q

HC(=O)H

with water

A

CH2(OH)2

173
Q

Carboxylic acid

with 2 R-Li

A

Ketone

174
Q

Nitrile

with (1) OM and (2) Acid

A

Ketone

175
Q

Nitrole

with (1) DIBAL-H and (2) Acid

A

Aldehyde

176
Q

Carboxylic acid

with SOCl2

A

Acid chloride

177
Q 
Acid chloride
with LiAlH(OtBu)3
A

Aldehyde

178
Q

Acid or acid chloride or ester

with LAH

A

Primary alcohol

179
Q

Ester

with cold DIBAL-H then water

A

Aldehyde

180
Q

Acid chloride

with R2CuLi

A

Ketone

181
Q

R2C=O

with -CN

A

R2C(OH)(CN)

182
Q

R2C=O

with H2N-Z

A

R2C=N-Z

183
Q

R2C=O

with 2 R’-OH

A

R2C(OR’)2

184
Q

R2C=O

with diol

A

Cyclic acetal!

185
Q

Aldehyde

with any [O]

A

Acid

186
Q

Aldehyde

with Ag2O

A

Tollens test: Acid– selective!

187
Q 
Aldehydes and ketones
with NaBH(OAc)3
A

Acids and ketones

188
Q 
R2C=O
with Zn(Hg) in HCl
A

Clemmensen reduction: R2CH2

189
Q

R2C=O

with (1) H2NNH2 then (2) KOH

A

Wolff-Kishner reduction: R2CH2

190
Q

R’NH2

with RCOCl

A

RCONHR’

191
Q

Reagent to exhaustively methylate amines?

A

MeI

192
Q

NH4OH

with heat

A

Hoffman elimination: alkene + amine + water

193
Q

Reagent used to convert NH4I to NH4OH?

A

Ag2O, H2O

194
Q

Amine

with (1) excess CH3I then (2) Ag2O, H2O

A

Hoffman elimination: alkene (Hoffman product)

195
Q

Secondary amine

with HOOH

A

Hydroxylamine

196
Q

Tertiary amine

with HOOH

A

Amine oxide (R3N-O)

197
Q

Amine oxide

A

Cope elimination: syn, Hoffman alkene

198
Q

Primary amine

with NaNO2

A

R-N+(trip)N –> N2 and C+’s

199
Q

Secondary amine

with NaNO2

A

R2NN=O

200
Q

Ar

with HNO3 in H2SO4

A

Ar-NO2

201
Q

Ar-NO2

with Fe, HCl then OH

A

Ar-NH2

202
Q

Ar-NH2

with NaNO2 in HCl

A

Ar-N(+)(trip)N

203
Q

Ar-N(+)(trip)N + what = Ar-OH?

A

H3O+, warm

204
Q

Ar-N(+)(trip)N + what = Ar-Cl?

A

CuCl

205
Q

Ar-N(+)(trip)N + what = Ar-Br?

A

CuBr

206
Q

Ar-N(+)(trip)N + what = Ar-C(trip)N

A

CuCN

207
Q

Ar-N(+)(trip)N + what = Ar-F

A

HBF4

208
Q

Ar-N(+)(trip)N + what = Ar-I

A

KI

209
Q

Ar-N(+)(trip)N + what = Ar-H

A

H3PO2

210
Q

Ar-N(+)(trip)N + what = Ar-N=N=Ar’

A

H-Ar’

211
Q

x-ary amine

with (1) carbonyl then (2) hydride

A

(x+1)-ary amine

212
Q

Amine

with acid chloride

A

Amide

213
Q

Amine

with (1) acid chloride then (2) hydride

A

Alkylated amine via amine

primary alkyl group

214
Q

Ammonia

with halide or tosylate

A

Sn2: primary amine

215
Q

Protected NH3

with RX then H2NNH2

A

Gabriel amine synthesis: R-NH2

216
Q

R-X/Ts; primary or secondary

with (1) N3- then (2) H- or H2/Pd

A

RNH2

217
Q

R-X/TS; primary or secondary

with (1) -CN then (2) H- or H2/Pd

A

R-CH2-NH2

218
Q

Three things that change R-NO2 to R-NH2:

A

1) H2/cat
2) H+/met
3) H-

219
Q

Methanol + CO

with Rh catalyst

A

CH3COOH

220
Q

Toluene

with strong [O]

A

Benzoic acid

221
Q

Methyl ketone

with X2 in base

A

R-COO- + HCX3

222
Q 
R-COOH
with CH2N2 (diazomethane)
A

Methyl ester + N2

223
Q

Carboxylic acid + amine

with heat

A

Amide

224
Q

Carboxylic acid

with LAH

A 
Primary alcohol
(other C=O's reduced)
225
Q

Carboxylic acid

with boron reagent

A 
Primary alcohol
(other C=O's unaffected)
226
Q

How to make an acid an aldehyde?

A

Convert to acid chloride, then treat with LiAlH(OtBu)3

227
Q

Acid

with SOCl2 or (COCL)2

A

Acid chloride + gas

228
Q

How to make an acid an ester?

A

Convert to acid chloride, then react with alcohol

229
Q

How to make an acid an amide (not heat)?

A

Convert to acid chloride, then react with amine

230
Q

Nitrile

with water in acid

A

Primary amide then carboxylic acid

231
Q

Carboxylic acid

with ammonia, heat

A

Primary amide

232
Q

Primary amide

with POCl3

A

Nitrile

233
Q

How to make a nitrile from an acid?

A

First ammonia and heat, then POCl3

234
Q

Acid chloride to acid anhydride with…?

A

Carboxylic acid

235
Q

Acid chloride to ester with…?

A

Alcohol

236
Q

Acid chloride to amide with…?

A

Ammonia/amines (excess or with base)

237
Q

Frequent product of acid chloride interconversion?

A

HCl

238
Q

Acid anhydride to ester with…?

A

Alcohol (1 acid unit = LG)

239
Q

Acid anhydride to amide with…?

A

Ammonia/amines

240
Q

RCOOR’

with excess R’‘-OH

A

Transesterification:

RCOOR’’ + R’-OH

241
Q

Ester

with excess water

A

Carboxylic acid and alcohol

242
Q

Ester

with hydroxide

A

Saponification:

Carboxylate and alcohol

243
Q

What can LAH reduce to alcohols?

A

Acids, acid chlorides, anhydrides, and esters

244
Q

What can LAH reduce to amines?

A

Amides and nitriles

245
Q

Acid chloride or ester

with 2 OMR

A

Tertiary alkoxide

246
Q

Nitrile reduction via OMR?

A

OMR gives imine; acid hydrolysis gives ketone

247
Q

Hydroxy acid

A

Cyclic ester (lactone) and water

248
Q

Amino acid

A

Cyclic amide (lactam) and water

249
Q

CO2

with water

A

H2CO3

250
Q

Ketone or aldehyde

with secondary amine

A

Enamine (N equivalent of enol)

251
Q

Iminium (+N=C) salt

with acid

A

Ketone

252
Q

Ketone

with X2 in base

A

alpha-haloketone

multiple halogenations

253
Q

Ketone

with X2 in acid

A

alpha-haloketone

can stop at monohalogenation

254
Q

Aldehyde

with X2 in water

A

Carboxylic acid + 2HX

255
Q

HVZ reaction

A

Carboxylic acid with Br2/PBr3 to bromo acyl bromide. Add reagent to give alpha bromo acid or other derivative.

256
Q

Aldol condensation

A

Carbonyl C of one ket/ald reacts with alpha C of another to give aldol, which can dehydrate to unsaturated ket/ald

257
Q

Claisen ester condensation

A

Two esters combine to give a beta-keto ester

258
Q

Dieckmann condensation

A

Internal Claisen condensation of diester to form ring

259
Q

Malonic ester synthesis

A

Makes substituted derivatives of acetic acid

260
Q

Acetoacetic ester synthesis

A

Makes substituted derivatives of acetone

261
Q

Michael addition

A

Nucleophilic 1,4-addition by doubly stabilized carbanion to beta carbon of conjugated system

262
Q

Robinson annulation

A

Intramolecular aldol condensation of delta-diketone to form a 6-membered ring; dehydration gives alkene

263
Q

Polyamide (nylon) building blocks

A

-NH-Y-NH-(C=O)-Z-(C=O)-

264
Q

Polyester building blocks

A

-O-Y-O-(C=O)-Z-(C=O)-

265
Q

Polycarbonate building blocks

A

-O-Y-O-(C=O)-

C=O from XCOX

266
Q

Polyurethane building blocks

A

-O-Y-O-(C=O)-(NH)-Z-(NH)-(C=O)-

Chem GRE (5 decks)

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