CHEM 372 Lecture Notes - Lecture 17: Malonic Ester Synthesis, Diethyl Malonate, Enol

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11 Aug 2015

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Chapter 23, 3rd edition: 1, 5-20, 21-28, 30, 32-34, 45-54, 58, 59, 64, 65. Chapter 23, 4th edition: 1, 2, 4-6, 10-13, 16-20, 21-28, 32-36, 38, 39, 44-48, 50-53, 58, 62. Warm-up problem: draw the products for the following reactions: Malonic ester synthesis: results in an alkylated carboxylic acid. Enolate alkylation (first set of steps: followed by hydrolysis and decarboxylation. Naoetbrooooh3o+oohheat123412233442. oooohoetna+oooobroooopka = 13sn2ooooh3o+oooohhco2oohhoohesterhydrolysis(seemechanism,3/17/09notes,p. 3)heatdecarboxylationketo-enoltautomerism since the malonic ester has two acidic protons, sometimes dialkylation can occur. The reaction can also form a cyclic alkane: Naoetbroooooohheat123412233442. br5br5oooonaoeth3o+512345acetoacetic ester synthesis: very similar reaction, results in a ketone. Overall reaction: enolate alkylation (first set of steps) note that there is more than one set of acidic protons. Why: alkylation is followed by hydrolysis and decarboxylation. Naoetbroooh3o+oheat2. ooohhoetna+ooobrooopka = 11, more acidic,so deprotonated atequilibriumpka = 19sn2oooh3o+ooohco2ohohydrolysisheatdecarboxylationo dialkylation can also occur for this reaction. Can a tertiary carbon be deprotonated in either the malonic ester synthesis or the acetoacetic ester synthesis: sure!

Related Questions

Give It Some Thought 6.16

Valence electron configurations of the elements.

Part A

The elements Ni, Pd, and Pt are all in the same group. By examining the electron configurations for these elements in the following figure, what can you conclude about the relative energies of the nd and (n+1)s orbitals for this group?

nd > (n+1)s

nd < (n+1)s

nd = (n+1)s

It is impossible to conclude.

Make a small table of the K_{\alpha } values from table 9.1 (included below), the K_{\alpha }(calc) value and the corrected value K_{\alpha }^{*} (calc) along with the \lambda_{K_{\alpha }} value from the experimental value and the value calculated from K_{\alpha }^{*} (calc) energy for the following elements: B, Na, Cl, Fe, and Ag. (note this is college upper level physical chemistry; I expect a full answer)

T A

0 0.481

1 0.476

2 0.471

3 0.466

4 0.460

5 0.454

6 0.449

7 0.445

8 0.440

9 0.435

10 0.430

11 0.425

12 0.420

13 0.415

14 0.411

15 0.408

16 0.403

17 0.399

18 0.394

19 0.390

20 0.385

21 0.380

22 0.375

23 0.372

24 0.367

25 0.362

26 0.359

27 0.357

28 0.355

29 0.348

30 0.343

31 0.339

32 0.335

33 0.332

34 0.328

35 0.324

36 0.321

37 0.317

38 0.314

39 0.311

40 0.307

41 0.304

42 0.301

43 0.297

44 0.295

45 0.293

46 0.289

47 0.285

48 0.283

49 0.280

50 0.277

51 0.274

52 0.272

53 0.270

54 0.267

55 0.264

56 0.261

57 0.259

58 0.257

59 0.254

60 0.251

61 0.248

62 0.246

63 0.244

64 0.241

65 0.240

66 0.240

67 0.239

68 0.233

69 0.228

70 0.225

71 0.223

72 0.221

73 0.220

74 0.218

75 0.219

76 0.216

77 0.211

78 0.208

79 0.206

80 0.205

81 0.203

82 0.200

83 0.198

84 0.197

85 0.194

86 0.192

87 0.190

88 0.188

89 0.186

90 0.184

91 0.182

92 0.180

93 0.178

94 0.177

95 0.174

96 0.173

97 0.171

98 0.170

99 0.168

100 0.167

101 0.165

102 0.163

103 0.162

104 0.159

105 0.158

106 0.156

107 0.155

108 0.153

109 0.151

110 0.149

111 0.149

112 0.147

113 0.146

114 0.144

115 0.143

116 0.141

117 0.140

118 0.138

119 0.137

120 0.136

121 0.135

122 0.134

123 0.132

124 0.131

125 0.130

126 0.128

127 0.126

128 0.125

129 0.125

130 0.123

131 0.122

132 0.121

133 0.120

134 0.119

135 0.118

136 0.117

137 0.116

138 0.115

139 0.114

140 0.114

141 0.114

142 0.111

143 0.110

144 0.109

145 0.108

146 0.107

147 0.106

148 0.105

149 0.105

150 0.104

151 0.103

152 0.103

153 0.102

154 0.100

155 0.100

156 0.099

157 0.099

158 0.098

159 0.097

160 0.096

161 0.096

162 0.095

163 0.094

164 0.094

165 0.093

166 0.092

167 0.092

168 0.091

169 0.090

170 0.090

171 0.089

172 0.088

173 0.087

174 0.087

175 0.086

176 0.085

177 0.085

178 0.084

179 0.084

180 0.084

181 0.083

182 0.082

183 0.081

184 0.076

185 0.055

186 0.053

187 0.053

188 0.052

189 0.052

190 0.051

191 0.052

192 0.053

193 0.051

194 0.049

195 0.049

196 0.049

197 0.048

198 0.047

199 0.047

200 0.047

Using excel, analyze the data graphically to decide if the reaction is zero, first or second order with respect to crystal violet.

1. was the reaction zero, first or second order, with respect to the concetration of crystal violet? Explain

2. Calculate the rate, K, using the slope of the linear regression line for your linear curve (k= --slope for zero and first order and K= slope for second order.) Be sure to include correct units for the rate constant

3. Write the correct rate law expression for the reaction, in terms of crystal violet (Omit OH-)

4. Using the data table, estimate the half-life of the reaction; select two points, one with an absorbance value that is about half of the other absorbance value. The time it takes the absorbance (or concentration) to be halved is known as the half life for the reaction

CHEM 372 Lecture Notes - Lecture 17: Malonic Ester Synthesis, Diethyl Malonate, Enol

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