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Chemical Engineering Licensure Exam Oct. 2023 > Organic Chemistry (Reactions only) (Done) > Flashcards

Organic Chemistry (Reactions only) (Done) Flashcards

Questions give the reactant and you are asked about the product

1
Q

Oxidation of ketone with KMnO4 yields

A

Carboxylic acid

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2
Q

Reaction of carboxylic acid with chlorine yields _ then forms _ in the presence of ammonia

A

Acid chloride, amide

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3
Q

Hydrogenation of alkene yields

A

Alkane

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4
Q

Addition of alcohol to aldehyde or ketone yields

A

Hemiacetal, then further addition results to acetal

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5
Q

Reduction of aldehyde with LiAlH4 or NaBH4 yields

A

Primary alcohol

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6
Q

Oxidation of aldehyde with KMnO4 / Ag2O and HO- in acidic medium yields

A

Carboxylic acid

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7
Q

Reaction of Diazonium salt with Cu2Cl2 in heat yields

A

Chlorobenzene and N2

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8
Q

Reduction of alkyne using Pd or Ni-B yields

A

Cis alkenes

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9
Q

Oxidation of alkylbenzenes with KMnO4, HO-, heat then H3O+ yields

A

Benzoic acid, CO2

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10
Q

Reaction of diazonium salt with KI in heat yields

A

Iodobenzene and N2

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11
Q

Reduction of acyl chloride with LiAlH(O-t-butyl) and water yields

A

Aldehyde

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12
Q

Reduction of alkyne using Na or Li, NH3 yields

A

Trans alkenes

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13
Q

Hydroxylation of alkene in cold, dilute, neutral KMnO4 yields

A

Syn-diol

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14
Q

Sulfonation of benzene yields

A

Benzenesulfonic acid

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15
Q

Hydrogenation of alkynes in Lindlar’s Catalyst (Pd (Pb)) yields

A

cis-alkene

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16
Q

Reaction of ether with HX (X = I or Br) in excess yields

A

Lower order alcohol and higher order alkyl halide

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17
Q

Reaction of carboxylic acid with acyl chloride in base (NaOH, pyridine) yields

A

(Acid) anhydride

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18
Q

Reaction of acyl chloride with sodium acetate yields

A

Acid anhydride

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19
Q

Oxidation of tertiary alcohol yields

A

No reaction

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20
Q

Reaction of ether with HX (X = I, Br) yields

A

Lower order alkyl halide, higher order alcohol

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21
Q

Use of HX on alcohol yields

A

Alkyl halide

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22
Q

Oxidation of methylketone with X2 in NaOH then H3O+ yields

A

Carboxylic acid and haloform

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23
Q

Hydration of alkyne using water, H+ and HgSO4 yield

A

Keto-enol (ketone and enol in tautomerism)

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24
Q

Reaction of acyl chloride with ammonia yields

A

Amide

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25
Q

Hydrohalogenation of alkenes yields

A

Alkyl halides

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26
Q

Use of SOCl2 on primary or secondary alcohol yields

A

Alkyl halide

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27
Q

Grignard synthesis on alkyl halide yields

A

Alkane

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28
Q

Use of Grignard Reagent or Organolithium Compound on ketone yields

A

Tertiary alcohol

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29
Q

Use of K2Cr2O7, CrO7, H2CrO4 on secondary alcohol for oxidation yields

A

Ketone

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30
Q

Friedel-Crafts Acylation of benzene/aromatic hydrocarbon yields

A

Aromatic ketone

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31
Q

Reduction of alkyl halide by metal and acid yields

A

Alkane

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32
Q

Reaction of ester with alcohol in acidic or basic medium yields

A

Another ester and another alcohol

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33
Q

Reduction of amide with LiAlH4 yields

A

Amine

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34
Q

Use of PCC with CH2Cl2 and heat on primary alcohol yields

A

Aldehyde

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35
Q

Addition of Grignard or Organolithium reagent on nitrile yields

A

Ketone

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36
Q

Fridel-Crafts Alkylation of benzene yields

A

Alkylbenzene

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37
Q

Reaction of nitrile with DIBAL-H and water yields

A

Aldehyde

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38
Q

Reaction of carboxylic acid with halogen yields

A

Alpha-haloacid

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39
Q

Reaction of ester with Grignard Reagent yields

A

Tertiary alcohol

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40
Q

Addition of 2HX to alkyne yields

A

Geminal dihalide

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41
Q

Ozonolysis of alkyne yields

A

Carboxylic acid (main product) and CO2

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42
Q

Alkene + X2 (X is a halogen) in water yields

A

Halohydrin

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43
Q

Hydrolysis of nitriles yield

A

Carboxylic acid

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44
Q

Oxidation of alkylbenzenes in KMnO4, HO-, heat then H3O+ yield

A

Benzoic acid and CO2

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45
Q

Alcoholysis of acid anhydrides yield

A

Esters (main product) and carboxylate/carboxylic acid

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46
Q

Reduction of ketone yields _ while further reduction yields _

A

Secondary alcohol, alkane

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47
Q

Reduction of carboxylic acid yields _ and can form _

A

Carboxylate, salts

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48
Q

Oxidation of aldehyde with KMnO4 / Ag2O OH- (in acidic conditions) yields

A

Carboxylic acid

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49
Q

Addition of Grignard Reagent or Organolithium compound to ketone yields

A

Tertiary alcohol

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50
Q

Baeyer-Villiger oxidation of aldehyde yields

A

Carboxylic Acid

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51
Q

Hydrolysis of acid chloride yields

A

Carboxylic acid and HCl

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52
Q

Dehydration of alcohol yields

A

Alkenes

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53
Q

Addition of a primary amine to a ketone yields

A

Imine derivative

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54
Q

Reaction of carboxylic acid with ammonia yields

A

Amide

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55
Q

Halogenation of alkane in extreme conditions (UV/heat/light) yields

A

Alkyl halide

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56
Q

Dehydrohalogenation of alkyl (vicinal) dihalides yields

A

Alkynes

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57
Q

Reaction of diazonium salt with Cu2(CN)2 in heat yields

A

Benzonitrile and N2

58
Q

Reaction of ester with DIBAL-H and water yields

A

Aldehyde

59
Q

Addition of ketone to Grignard reagent yields

A

Tertiary Alcohol

60
Q

Addition of hydroxylamine to aldehyde yields

A

Oxime derivative

61
Q

Use of SOCl2 on tertiary alcohol yields

A

No reaction because tertiary carbons cannot undergo SN2

62
Q

Oxidation of alkene (1. KMnO4, HO- 2. heat 3. H3O+) yields

A

Ketone and carboxylic acid (if the other C is connected to an R group) or CO2 (if it is connected to just an H)

63
Q

Reaction of haloalkane with ammonia yields

A

Amine

64
Q

Oxidation of primary alcohol using a strong oxidizing agent (KMnO4 with HO-, H2O and heat) yields

A

Carboxylic acid

65
Q

Reaction of diazonium salt with Cu2Br2 in heat yields

A

Bromobenzene and N2

66
Q

Reaction of carboxylic acid with sodium acetate yields

A

Acid anhydride

67
Q

Oxidation of alkyne (1. KMnO4, HO-, heat 2. H3O+) yields

A

Carboxylic acid and CO2

68
Q

Williamson Synthesis of alkyl halide and sodium alkoxide yields

A

Ether

69
Q

Combustion/oxidation of alkane yields

A

CO2 and H2O

70
Q

Addition of HX (X - halogen) to alkene yields

A

Alkyl halide

71
Q

Use of PX3 (X = halogen) on primary and secondary alcohol yields

A

Alkyl halide

72
Q

Reaction of acid anhydride with primary and secondary amine yields

A

Amide

73
Q

SN2 favors _ carbons

A

Primary

74
Q

Use of Grignard Reagent or Organolithium Compound on methanal/formaldehyde yields

A

Primary alcohol

75
Q

Dehalogenation of tetrahalides in 2 Zn yields

A

Alkynes

76
Q

Reaction of sodium acetylide with alkyl halides yield

A

Alkynes

77
Q

Reaction of carboxylic acid with PCl3, PCl5 or SOCl3 yields

A

Acyl/acid chloride

78
Q

Reaction of carboxylic acid with primary alcohol in acidic condition yields

A

Ester

79
Q

Oxidation of alkyne (1. O3 2. Zn, Water) yields

A

Carboxylic acid and carbonic acid

80
Q

Oxymercuration-demercuration of alkene yields

A

Alcohol

81
Q

Reduction of carboxylic acid using LiAlH4 yields

A

Primary alcohol

82
Q

Hydrolysis of amide in basic conditions then heated yields

A

Carboxylic acid and ammonia

83
Q

Use of Na, K or NaH on an alcohol then reaction with methyl halide yields

A

Ether (unsymmetrical)

84
Q

Use of H2SO4 in 140 degC to dehydrate an alcohol yields

A

Ether (symmetrical)

85
Q

Reduction of nitrobenzene with Fe and HCl yields

A

amine (aniline)

86
Q

Ozonolysis of alkene yields

A

Ketone and aldehyde

87
Q

Hydrogenation of alkyne yields

A

Alkane

88
Q

Addition of HCN to aldehyde yields

A

Cyanohydrin derivative

89
Q

Baeyer-Villiger oxidation of ketone yields

A

Ester

90
Q

Reaction of carboxylic acid with tertiary amine yields

A

No reaction because no other hydrogen

91
Q

Ring substitution of carboxylic acid results in

A

meta placement of NO2

92
Q

Use of PX3 (X = halogen) on tertiary alcohol yields

A

No reaction because tertiary carbons cannot undergo SN2

93
Q

Reaction of acid anhydride with ammonia yields

A

Amide, ammonium carboxylates

94
Q

Hydroxylation of alkene in peroxy acid

A

Anti-diol

95
Q

Use of Grignard Reagent or Organolithium Compound on formaldehyde and epoxide yields

A

Primary alcohol

96
Q

Reaction of amine with strong acid yields

A

Salt

97
Q

Hydration of ester yields

A

Carboxylic acid, alcohol

98
Q

Partial oxidation of methane yields

A

Carbon monoxide and hydrogen

99
Q

SN1 favors _ carbons

A

Tertiary

100
Q

Reduction of nitrile with 2 H2, Raney Ni yields

A

Amine

101
Q

Hydrolysis of alkyl halides yields

A

Alcohol

102
Q

Acid-catalyzed hydration (H+, water) of alkene yields

A

Alcohol

103
Q

Reduction of ester using LiAlH4 and H3O+ yields

A

Two primary alcohols

104
Q

Nitration of benzene yields

A

Nitrobenzene

105
Q

Aniline reacted with HNO2 in low temp yield

A

Diazonium salt

106
Q

Corey House synthesis yields

A

Alkane

107
Q

Reaction of diazonium salt with water yields

A

Phenol and N2

108
Q

Reaction of ester in NaOH yields

A

Carboxylate, alcohol

109
Q

Addition of HCN to a ketone yields

A

Cyanohydrin derivative

110
Q

Addition of 2,4-Dinitrophenylhydrazine to ketone yields

A

2,4-Dinitrophenylhydrozone derivative

111
Q

Hydration of acid anhydride yields

A

Carboxylic acid

112
Q

Hydrogenation of alkyne in the presence of Na or Li in NH3 or C2H5NH2 in low temperature yield

A

trans-alkene

113
Q

Pyrolysis/cracking of alkane yields

A

Hydrogen, smaller alkanes and alkenes

114
Q

Oxidation of alkene with KMnO4, HO-, heat then H3O+ yields

A

Two carboxylic acids

115
Q

Reduction of nitro compound with LiAlH4 yields

A

Amine

116
Q

Benzenesulfonic acid in NaOH, fuse yield

A

Phenol

117
Q

Reduction of acid chloride using a bulky hydride source yields

A

Aldehyde

118
Q

Wurtz synthesis yields

A

Alkane

119
Q

Halogenation of alkyne yield

A

Alkyl halide

120
Q

Wolff-Kishner reduction of ketone yields _ then _ when heated

A

Hydrozone derivative, alkane

121
Q

Reaction of alcohols in the presence of metals yields

A

Metal alkoxide

122
Q

Dehydrogenation of alkyl halides yields

A

Alkenes

123
Q

Reaction of diazonium salt with H3PO2 (aka hypophosphorous acid or phosphinic acid) yields

A

Benzene, N2 and phosphorous acid

124
Q

Reduction of ketone with LiAlH4 or NaBH4 yields

A

Secondary alcohol

125
Q

Reaction of acyl chloride with primary and secondary amine yields

A

Amide

126
Q

Reaction of acyl chloride with tertiary amine yields

A

No reaction

127
Q

Oxidation of secondary alcohols with PCC, CH2Cl2 and heat yields

A

Ketone

128
Q

Reaction of carboxylic acid with primary and secondary amine yields

A

Amide

129
Q

Hydroboration-Oxidation of alkene yields

A

Alcohol

130
Q

Halogenation of alkenes in CCl4 yields

A

Vicinal dihalide

131
Q

Debromination of dibromide in Zn yields

A

Alkenes

132
Q

Carbonation (CO2) of Grignard reagent yields

A

Carboxylic Acid

133
Q

Reaction of acyl chloride with primary alcohol yields

A

Ester

134
Q

Addition of Grignard Reagent or Organolithium compound to aldehyde yields

A

Secondary alcohol

135
Q

Oxidation of primary alcohol with weakly oxidizing agent (K2Cr2O7) yields

A

Aldehyde, then carboxylic acid

136
Q

Halogenation of alkene with heat or UV yields

A

Allyl halides

137
Q

Use of Grignard Reagent or Organolithium Compound on aldehyde yields

A

Secondary alcohol

138
Q

Addition of phenylhydrazine to ketone yields

A

Phenylhydrozone derivatives

139
Q

Halogenation of benzene yields

A

Halobenzene

140
Q

Friedel-Crafts alkylation of benzene yields

A

Alkylbenzene

141
Q

Dehydrogenation of vicinal dihalides yields

A

Alkenes

Chemical Engineering Licensure Exam Oct. 2023 (3 decks)

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