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1、 C H COOH CH3CH2 H3C H3CC2H5 H COOH C2H5COOH H CH3 HC2H5 A B C H3CH COOH C2H5 H CH3 COOH HCH3 H3CH C2H5 COOH HCH3 D E F G H COOH CH3 C2H5 COOH C2H5 C2H5 COOH s 1 1 How would you synthesize by using an acid chloride or ester CH3CH2CCH3 OH CH3 C OH CH3 2 How would you synthesize CH3CH2CHCH2CH2CH3 OH O
2、H CH3 3 2 4 3 5 6 4 7 8 5 9 10 1 1 Each of the following reactions has been reported in the chemical literature and gives a single organic product in good yield What is the principal product in each reaction 2 2 Wolff Kishner reduction hydrazine KOH ethylene glycol 130C of the following compound sho
3、wn gave compound A Treatment of compound A with m chloro peroxybenzoic acid gave compound B which on reduction with lithium aluminum hydride gave compound C OxidationofcompoundCwithchromicacidgave compound D C9H14O Identify compounds A through D in this sequence and the related reactions 3 3 Synthes
4、es of each of the following compounds have been reported in the chemical literature Using the indicated starting material and any necessary organic or inorganic reagents describe short sequences of reactions that would be appropriate for each transformation 4 4 The following five step synthesis has
5、been reported in the chemical literature Suggest reagents appropriate for each step ab c de 5 5 A compound C11H14O has a strong peak in its infrared spectrum near 1700 cm 1 Its 200 MHz 1H NMR spectrum is shown in following What is the structure of the compound 6 6 Compounds A and B are isomeric dike
6、tones of molecular formula C6H10O2 The 1H NMR spectrum of A contains two signals both singlets at 2 2 6 H and 2 8 ppm 4 H The 1H NMR spectrum of B contains two signals one at 1 3 ppm t 6H and the other at 2 8 ppm q 4 H What are the structures of compounds A and B 7 Suggest reasonable mechanism for e
7、ach of the following reactions 7 8 Hydride reduction with LiAlH4or NaBH4 of each of the following ketones has been reported in the chemical literature and gives a mixture of two diastereomeric alcohols in each case Give the structures or build molecular models of both alcohol products for each keton
8、e 8 9 Each of the following reactions has been reported in the chemical literature Write the structure of the product s formed in each case 9 10 Identify the reagents appropriate for each step in the following syntheses 10 11 Outline reasonable mechanisms for each of the following reactions 11 12 12
