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CBSE Chemistry > Organic Chemistry 4 > Flashcards

Organic Chemistry 4 Flashcards

1
Q

Define Hydrogenation

A

addition of H2 to a multiple bond

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2
Q

Hydrogenation

A

alkene to alkane

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3
Q

Notes on Hydrogenation

A

syn addition

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4
Q

H2/Pd, Pt, or Ni

A

Hydrogenation

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5
Q

How does heat affect stability?

A

less heat = more stable more heat = less stable

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6
Q

Syn Addition

A

two atoms or groups add to the same face of a double bond

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7
Q

Anti Addition

A

atoms or groups add to opposite faces of the double bond

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8
Q

Stereoselectivity

A

a reaction in which a single starting material can give two or more stereoisomeric products but yields one of them in greater amounts than the other

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9
Q

slowest to fastest rate of addition

A

HF«HI

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10
Q

weakest acid to strongest acid HI, HF, HCL, HBR

A

HF«HI

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11
Q

Markovnikov’s Rule

A

when an unsymmetrically substituted alkene reacts with a hydrogen halide, the hydrogen adds to the carbon that has the greater number o fhydrogesn, and the halogen adds to the carbon having fewer hydrogens

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12
Q

Name the mechanism and any rule that applies: CH3CH2CH=CH2 + HBR CH3CH2CH(BR)CH3

A

Hydrohalogenation and markovnikov’s rule

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13
Q

Define Hydrohalogenation

A

is the electrophilic addition of hydrohalic acids like hydrogen chloride or hydrogen bromide to alkenes to yield the corresponding haloalkanes

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14
Q

Hydrohalogenation

A

Alkene to alkyl halide Alkyne to Alkenyl Halide Alkyne to Geminal dihalide

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15
Q

Notes on Hydrohalogenation

A

Markovnikov’s Rule

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16
Q

Hydrogen Halide ex: HBR, HCL

A

Hydrohalogenation

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17
Q

Define Dehydration

A

loss of water

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18
Q

Dehydration

A

alcohol to alkene

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19
Q

What kind of mechanism does Dehydration take place

A

E1-carbocation E2-no carbocation

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20
Q

H2SO4 or H3PO4

A

Dehydration

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21
Q

Elimination 1

A

alcohol to alkene carbocation present H2SO4 or H3PO4 TERTIARY weak NU, weak base (NH3/CH3NH2/C5H5N or pyridine), heat SECONDARY heat, weak base, weak NU, good LG, steric hindrance

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22
Q

Elimination 2

A

alcohol to alkene no carbocation H2SO4 or H3PO4 PRIMARY strong bulky base sterically hindered SECONDARY strong base sterically hindered secondary LG

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23
Q

SN2

A

nucleophillic substitution chirality present=stereochem achiral present=no stereochem PRIMARY aprotic solvent,good NU,strong/weak base, unhindered SECONDARY aprotic solvent, good NU, unhindered, inversion, backside attack), no carbocation

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24
Q

SN1

A

carbocation forms enantiomers TERTIARY protic solvent, good NU, forms enantiomers SECONDARY protic solvent, good NU,

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25
Q

Very Good NU

A

I, HS, RS

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26
Q

Good NU

A

Br, OH, RO, CN, N3

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27
Q

fair NU

A

NH3, Cl, F, RCO2

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28
Q

Weak NU

A

H20, ROH

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29
Q

Very Weak NU

A

RCO2H

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30
Q

Aprotic Solvents examples

A

no hydrogen bonding; no acidic hydrogen; stabilize ions; favor SN2 EXAMPLES DCM, THF, ethyl acetate, acetone, DMF, MeCN or acetonitrile, DMSN or dimethyl sulfoxide,

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31
Q

Protic Solvents examples

A

hydrogen bonding; acidic hydrogen; cations and anions;favor SN1 EXAMPLES Formic acid, n-Butanol, isopropanol, ethanol, methanol, acetic acid, water

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32
Q

Primary

A

SN2 E2

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33
Q

Tertiary

A

SN1 E1

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34
Q

Secondary

A

all four

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35
Q

alkyl halide/AgNO3/aq. EtOH

A

SN1

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36
Q

Alkyl Halide/NaI/acetone

A

SN2

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37
Q

Alcohol/HX

A

SN1

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38
Q

alcohol/SOCl2 or PX3

A

SN2

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39
Q

alkyl halide/H2O

A

E1

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40
Q

alkyl halide/KOH/heat

A

E2

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41
Q

alcohol/H2SO4/heat

A

E1

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42
Q

Dehydrohalogenation

A

alkyl halide to alkene

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43
Q

What kind of mechanism is Dehydrohalogenation

A

E2

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44
Q

Strong Base

A

Dehydrohalogenation of E2

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45
Q

Free Radical Addition of HBR

A

Alkene to Alkyl Bromide

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46
Q

Notes on Free Radical Addition

A

Anti-Mark peroxides needed

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47
Q

HBR, Peroxides

A

Free Radical Addition of HBR

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48
Q

Hydration

A

Alkene to alcohol Alkyne to ketone

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49
Q

Notes on Hydration

A

Markovnikov’s

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50
Q

dilute H2SO4, H20

A

Hydration

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51
Q

Hydroboration-oxidation

A

Alkene to alcohol

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52
Q

Notes on Hydroboration-oxidation

A

Syn addition, anti-mark

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53
Q

1.B2H6, diglyme/2.H2O2, OH

A

Hydroboration-oxidation

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54
Q

Halogenation

A

Alkene to vicinal dihalide alkene to vicinal halohydrin alkyne to vicinal dihalide-trans alkene alkyne to tetrahalide

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55
Q

Notes on Halogenation

A

anti addition, OH adds to more substituted Carbon

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56
Q

X2, CHCL3, or CCl4

A

Halogenation

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57
Q

X2, H2O

A

Halogenation alkene to vicinal halohydrin

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58
Q

Epoxidation

A

Alkene to epoxide (carboxylic acid)

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59
Q

Notes on Epoxidation

A

Syn addition

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60
Q

peroxy acid

A

Epoxidation

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61
Q

Ozonolysis

A

Alkene to aldehydes or ketones alkyne to 2 carboxylic acids

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62
Q

Notes on Ozonolysis

A

Ozonide is intermediate

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63
Q
  1. O3/ 2. H2O, Zn or (CH3)2S
A

Ozonolysis

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64
Q

Formation of alkyl tosylate

A

alcohol to alkyl tosylate

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65
Q

Notes on alkyl tosylate

A

-OTs is leaving group

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66
Q

Tosylate chloride

A

Alkyl Tosylate

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67
Q

Formation of Alkyne Anion

A

Terminal Alkyne to Alkyne anion (conj. base) Na, NH3

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68
Q

NaNH2, NH3

A

Alkyne Anion

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69
Q

Alkylation

A

Alkyne anion to alkyne

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70
Q

Notes on Alkylation

A

Alkyne anion is LG

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71
Q

Methyl or primary alkyl halide

A

Alkylation

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72
Q

Formation of Alkyne

A

Vicinal dihalide to alkyne

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73
Q

Notes of formation of alkyne

A

double dehydro-halogenation

74
Q
  1. 2NaNH2, NH3/ 2. H2O
A

Formation of alkyne

75
Q

Hydrogenation of Alkynes

A

alkyne to alkane

76
Q

2H2/Pt, Pd, or Ni

A

Hydrogenation of Alkynes alkyne to alkane

77
Q

Lindlar Reduction

A

alkyne to cis alkene

78
Q

Notes on Lindlar Reduction

A

Syn Addition

79
Q

H2/CaCO3

A

Lindlar Reduction

80
Q

Metal Ammonia Reduction

A

alkyne to trans alkene

81
Q

Notes on Metal Ammonia Reduction

A

free radical intermediates

82
Q

Na or Li/NH3

A

alkyne to trans alkene

83
Q

X2

A

Alkyne to vicinal dihalide-trans alkene;halogenation

84
Q

2X2

A

Alkyne to tetrahalide/halogenation

85
Q

HX

A

alkyne to alkenyl halide;hydrohalogenation

86
Q

2HX

A

Alkyne to geminal dihalide;hydrohalogenation

87
Q
  1. H20/ 2. H2SO4, HgSO4 (HgO)
A

alkyne to Ketone;hydration

88
Q
  1. O3/ 2. H2O
A

Alkyne to 2 Carboxylic Acids;ozonolysis

89
Q

1* alcohol + Na2Cr2O7/H2SO4

A

aldehyde intermediate then to carboxylic acid

90
Q

2* alcohol + Na2Cr2O7/H2SO4

91
Q

1* alcohol + PCC (CrO3+pyridine+HCl)

92
Q

chromic acid test

A

1* and 2* alcohol will react, 3* wont

93
Q

Collins reagent

A

original PCC

94
Q

Jones reagent

A

Dilute Chromic Acid in acetone

95
Q

NaOCl/H2O

A

good oxidizer for acid sensitive compounds. Takes 1* all the way to a carboxylic acid

96
Q

alcohol + KMnO4 in base or water

A

1* to carboxylic acids, 2* to ketones

97
Q

HNO3/10-20*C

A

1* to carboxylic acids, 2* to ketones

98
Q

alcohol + CuO +heat

A

oxidation, not good for lab synthesis due to high temps

99
Q

alcohol + Cu-Zn/400*C

A

oxidation, not good for lab synthesis due to high temps

100
Q

alcohol + DMSO + oxyalyl chloride then hindered base (like Et3N) and low temps (Swern Oxidation)

A

to aldehydes and ketones

101
Q

alcohol + TsCl/pyridine

A

tosylate ester that can react via SN2

102
Q

alcohol + H2SO4/heat

A

alkene (reduction), can then react to form an alkane catalytically

103
Q

tosylate ester + LiAlH4

104
Q

alcohol + HBr/H2O

105
Q

alcohol + NaBr, H2SO4

106
Q

Alcohol + (lucas reagent) HCl/H2O –ZnCl2—>

107
Q

alcohol + PCl3

A

R-Cl + P(OH)3

108
Q

alcohol + PBr3

A

R-Br + P(OH)3

109
Q

alcohol + PCl5

A

R-Cl + POCl3 + HCl

110
Q

R-OH + P + I

A

R-I + P(OH)3

111
Q

R-OH + thionyl chloride (Cl2-S=O)–heat–>

A

chlorosulfite ester intermediate, then ion pair –> R-Cl + SO2 + HCl

112
Q

Alcohol —H2SO4, 180*C –>

A

E1 forms alkene

113
Q

(2)1* alcohol —H2SO4, 140*C –>

A

SN2 forms symmetrical dialkyl ethers

114
Q

diol –H2SO4/100* –>

A

one less OH group, ,ethyl shift to where OH was, double bond to O. PINACOL REARRANGEMENT

115
Q

alcohol + acid –H+ –>

A

ester + H2O

116
Q

alcohol + acid chloride

A

ester + HCl

117
Q

alcohol + sulfuric acid

A

alkyl sulfate ester, add another alcohol –> dialykl sulfate ester. really good leaving group

118
Q

alcohol + nitric acid

A

alkyl nitrate ester

119
Q

alcohol + phosphoric acid

A

phosphate ester

120
Q

Williamson Ether Synthesis

A

1) form alkoxide with Na, K or NaH 2) Sn2 attack of alkoxide on alkyl halide

121
Q

less hindered alkyl group (w/ halide or Ts) + more hindered alkoxide

A

williamson ether synthesis

122
Q

more hindered alky; group (w/ halide or Ts) + less hindered alkoxide

A

elimination

123
Q

R-X + Mg —ether–>

A

R-Mg-X, grignard reagent

124
Q

R-X + 2Li —>

A

R-Li(organolithium reagent) + Li+-X

125
Q

Formaldehyde + R-MgX –1)ether solvent, 2) H3O+ —>

A

1* alcohol

126
Q

Aldehyde + R-MgX –1)ether solvent, 2) H3O+ —>

A

2* alcohol

127
Q

Ketone + R-MgX –1)ether solvent, 2) H3O+ —>

A

3* alcohol, 1 group added

128
Q

acid chloride + 2R-MgX –1)ether solvent, 2) H3O+ —>

A

3* alcohol, 2 groups added

129
Q

ester + 2R-MgX –1)ether solvent, 2) H3O+ —>

A

3* alcohol, 2 groups added

130
Q

Ethylene Oxide + R-MgX –1)ether solvent, 2) H3O+ —>

A

1* alcohol, 2 carbons added

131
Q

R-MgX + compound containing O-H, N-H, S-H, or terminal alkyne

A

protonated reagent + alkane

132
Q

R-MgX + compound containing C=O, C=N, nitrile, S=O, N=O

A

will be attacked by reagent

133
Q

1* alcohol + Na(s)

134
Q

2* or 3* alcohol + K(s)

135
Q

difficult alcohol + NaH in THF

136
Q

Phenol + NaOH (aq) or KOH(aq)

137
Q

Why doesnt a phenol need to be treated with Na or K metal to form a phenoxide?

A

Ion formation is favored due to resonance stabilization

138
Q

aldehyde + 1)NaBH4, 2)H3O+

A

1* alcohol

139
Q

ketone + 1)NaBH4, 2)H3O+

A

2* alcohol

140
Q

carboxylic acid + 1)NaBH4, 2)H3O+

A

no reaction, NaBH4 is selective

141
Q

ester + 1)NaBH4, 2)H3O+

A

no reaction, NaBH4 is selective

142
Q

aldehyde + 1)LiAlH4, 2)H3O+

A

1* alcohol

143
Q

ketone + 1)LiAlH4, 2)H3O+

A

2* alcohol

144
Q

carboxylic acid + 1)LiAlH4, 2)H3O+

A

1* alcohol

145
Q

ester + 1)LiAlH4, 2)H3O+

A

1* alcohol

146
Q

alkene + 1)LiAlH4

A

no reaction

147
Q

alkene + NaBH4

A

no reaction

148
Q

aldehyde or ketone with double bonds + H2 –Raney Nickel–>

A

alcohol without double bonds

149
Q

Na+-S-H + R-X

A

R-SH (thiol)

150
Q

thiol + KMnO4 or HNO3

A

sulfonic acid (has 2 other resonance forms)

151
Q

R2CuLi(gilman reagent) +R’-X

A

R’-R + R-Cu + LiX

152
Q

2R-Li + CuI

A

R2CuI(gilman reagent formation) + LiI

153
Q

secondary alcohol + Na2Cr2O7, H2SO4 –>

154
Q

primary alcohol + Na2Cr2O7, H2SO4 –>

A

carboxylic acid

155
Q

primary alcohol + PCC –>

156
Q

alcohol + TsCl/pyridine, LiAlH4 –>

157
Q

Alcohol + HCl or SOCl/pyridine –>

A

alkyl halide (R-Cl)

158
Q

alcohol + HBr or PBr3 –>

A

alkyl halide (R-Br)

159
Q

Alcohol + H2SO4 or H3PO4 –>

160
Q

2R-OH + H+

A

R-O-R (ether)

161
Q

alcohol + TsCl/pyridine –>

A

alkyl tosylate (R-O-Ts)

162
Q

alcohol + acyl chliride –>

163
Q

alcohol + NaH –>

A

(alkoxide) R-O Na + H2

164
Q

R-O + R’-X –>

A

ether (R-O-R’) + X

165
Q

Alcohol –> alkene (1)

A

acid-catalyzed dehydration of alcohol

166
Q

Conversion of alcohols in alkyl halides (4)

A
  1. alcohol + alkyl halide by substitution 2. convert an alcohol to a sulfonate ester for alkyl chloride 3. alcohol + SOCL2 4. alcohol + PBr3
167
Q

Oxidation of alcohols

A

1a. primary alcohol + anhydrous chromium VI (aldehydes) 1b. primary alcohol + chromium VI (carboxylic acids) 2. secondary alcohol + chromium vi (ketones)

168
Q

Synthesis of alcohols from alkenes

A
  1. hydroboration-oxidation–follows Markovnikov’s Rule 2. oxymercuration-reduction–anti-Markovnikov’s Rule
169
Q

Synthesis of Ethers and Sulfides

A
  1. Williamson Ether Synthesis–alkylation of an alkoxide 2. Alkoxymercuration-Reduction 3. Alcohol dehydration to form ether 4. Alkene addition to form ether
170
Q

Synthesis of Epoxides

A
  1. Oxidation of Alkene with peroxycarboxylic acid 2. Cyclization of halohydrins (intra-molecular Williamson Ether Synthesis) 3.
171
Q

Cleavage of Ethers

A

Using acid of either concentrated or trace amounts

172
Q

Nucleophilic Substitution Reactions of Epoxides

A
  1. Ring Opening under Basic–at least substituted carbon 2. Ring Opening Under Acidic–at most substituted carbon 3. Reaction with Grignard reagents to add alkyl groups
173
Q

Preparation of Glycols

A
  1. Acid-catalyzed reaction of epoxide with h20 2. Oxidation of alkene with OsO4 3. Reaction with KMnO4
174
Q

Oxidative cleavage of glycol

A

using Periodic Acid

175
Q

Nitration

A

HNO3 H2SO4

176
Q

Sulfonation

177
Q

Hydrogenation

178
Q

Oxidation

179
Q

Bromination

180
Q

Chloronation

181
Q

Alkylation

A

CH3Cl AlCl3

182
Q

Acylation

A

CH3COCl AlCl3

CBSE Chemistry (5 decks)

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