Question

Image files ai.bmp.gdraw gif lico jpe jpeg Jpg .pct.pic.pict .png .svg .svgz tif tiff Show full mechanism of each step in the sequence of reactions leading to formation of 3-(2- oxopropyl)cyclohexanone (the structure is shown below). On the first step ethyl 3-oxobutanoate (the structure is shown below) reacts with 1 equivalent of sodium ethoxide in ethanol as a solvent. On the second step cyclohex-2-en-1-one reacts with the product of the first step. This step is Michael addition step. On the third step the product of the second step undergoes hydrolysis reacting with sodium hydroxide in water. On the last fourth step the compound obtained on the third step is heated to 180°C and undergoes decarboxylation reaction to form 3-(2-oxopropyl)cyclohexanone, (10 points) 3-(2-oxopropyl)cyclohexanone ethyl 3-oxobutanoate E Paragrach - BI EEP E R -

Answer 1

1. leque Navet, Etoh POEt ethyl 3-oxo butanoate o - 3-(2-oxopropyl / Cyclohexanone 3. NaOH, water 9. 4, 180°c first step :- NO Et (sodium ethoxide) is a strong base gives Na+%Et which abstracts highest acidie proton. The most acidic proton is the one between two e- with drawing keto group. at Nadet Etolt Hooget second step - the carboanion, generated in first Coß un saturated Ketone in Michel addition fashion . = the carboanion, generated in first step, attacks the TOET hex-2-en-l-one O enoliza ott third skep :- hydrolysis of ester group by one from Naoit. It is basic hydrolysis. NaO H, HỒ Fost" fourth step- decarboxylation of ß-keto acid upon healing. de enligting out 3-(2- Oxopropyl eyelohexanone