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assignment4answers - CHM 3120 Assignment 4 1 Give the...

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CHM 3120 Assignment 4 1. Give the product formed from the reaction with one equivalent of NaOEt followed by neutralization with acid. Ph OEt O NaOEt Ph OEt Ph O O Ph OEt O H + Ph OEt Ph O ONa Ph OEt O NaOEt -NaOEt Ph O EtO OEt Ph O Ph OEt Ph O O a) Ethyl phenylacetate H H EtO 2 C CO 2 Et Et OEt O NaOEt Et OEt Et O O EtO 2 C NaOEt Et OEt O H + OEt O EtO O Et OEt Et O ONa Et OEt O NaOEt CO 2 Et EtO O -NaOEt Et O EtO OEt Et O Et OEt Et O O CO 2 Et O b) Ethyl butyrate c) H H H OEt O NaOEt CO 2 Et O H + CO 2 Et O EtO 2 C CO 2 Et EtO 2 C NaOEt NaOEt OEt O EtO O OEt O EtO O CO 2 Et EtO O CO 2 Et EtO O CO 2 Et O CO 2 Et O d) H OEt O Alternate solution NaOEt H CO 2 Et O H + CO 2 Et O
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EtO OEt O O NaOEt O OEt O OEt O EtO OEt O O -OEt NaOEt H + ONa OEt O O OEt O O OEt O Ph O Ph OEt O Ph O OEt O Ph NaOEt Ph O Ph O Ph OEt O -OEt NaOEt H + Ph ONa Ph O Ph O Ph O Ph O Ph O e) and f) and + + H H H H CO 2 Et O OEt O CO 2 Et CO 2 Et O NaOEt CO 2 Et O OEt NaO NaOEt CO 2 Et OEt O O NaOEt CO 2 Et NaO O H + CO 2 Et O O CO 2 Et CO 2 Et O CO 2 Et O EtO O CO 2 Et O O -OEt g) This will be difficult and easily reversable H 2. Give the products of the following sequences
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a) b) Et OEt O O c) OMe O O NaOEt A B Br C NaOH D H 3 O + E Ph OEt O O NaOEt A B Ph Br C (CH 3 ) 3 COK D Br E NaOH F H 3 O + G NaOEt A B [ C ] (CH 3 ) 3 COK D Br Br E NaOH F H 3 O + G Et OEt O O (or other isomer) Et OEt O O Et O O O Et OH O O Et O Ph OEt O O (or other isomer) Ph OEt O O Ph Ph OEt O O Ph Ph OEt O O Ph Ph O O O Ph Ph OH O O Ph Ph O Ph (or other isomer) OMe O O (or other isomer) Note: error in original structure OEt O O Br OEt O O Br OEt O O O O O OH O O O
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d) EtO OEt O O NaOEt A B C A E CH 2 I 2 NaOH D H 3 O + F e) OEt O NaOEt A B C E D H 3 O + F N I (CH 3 ) 3 COK I NaOH G f) EtO 2 C CO 2 Et NaOEt [ A ] B C H 3 O + D I NaOH E EtO OEt O O EtO OEt
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