Question

The acetoacetic ester synthesis is a method for preparing

methyl

ketones from alkyl halides. For each of the following ketone

products, draw the structure of the alkyl chloride that

would

be

used in its synthesis.

Answer 1

5-chloro-2-methylpent-2-ene reacts with ethyl acetoacetate, in presence of NaOC2H5, C2H^OH and followed by NaOH, H2O to form 7-methyloct-6-en-2-one 1. Ethyl acetoacetate, CI 2. NaOH, H2O 3. H30", heat 5-chloro-2-methylpent-2-ene 7-methyloct-6-en-2-one Therefore, the alkyl chloride used in the above reaction is 5-chloro-2-methylpent-2-ene 1-chloro-2-methylpropane reacts with ethyl acetoacetate, in presence of NaOC2H5, C2HsOH and followed by NaOH, H20 to form 5-methylhexane-2-one 1. Ethyl acetoacetate CI 2. NaOH, H2O 3. H3O, heat 1-chloro-2-methylpropane Therefore, the alkyl chloride used in the above reaction is 1-chloro-2-methylpropane 1-(chloromethyl)-3,5-dimethylbenzene reacts with ethyl acetoacetate, in presence of NaOC2Hs, 5-methylhexan-2-one C2HOH and followed by NaOH, H2O to form 4-(3,5-dimethylphenyl)butane-2-one CI Ethyl acctoacetate, 2. NaOH, H2O 3. H3O, heat 1-(chloromethyl)-3,5-dimethylbenzene 4-(3,5-dimethylphenyl)butan-2-one Therefore, the alkyl chloride used in the above reaction is 1-(chloromethyl)-3,5-dimethylbenzene

Answer 2

Answer 3

The acetoacetic ester synthesis is a method for preparing methyl ketones from alkyl halides. For each o the following ketone products, draw the structure of the alkyl chloride that would be used in its synthesis Alkyl Chloride Reagents Ketone Product 1. Ethyl acetoacetate, 2. NaOH, H20 3. H30', heat CI 1. Ethyl acetoacetate, 2. NaOH, H20 3. H3O+, heat CI Ethyl acetoacetate, NaOC2Hs. C2H5OH Cl 2. NaOH, H20 3. H3Ợ, heat