Question

Propose an acetoacetic ester synthesis to generate each of thd following ketones:

3. Propose an acetoacetic ester synthesis to generate each of the following ketones:

Answer 1

1)Synthesisof Cyclohexyl methyl ketone Target Synthesis Na oEt CH,-CCH- c- O Et Et CH, -ETOH H. -B7 Aceto acetic ester (A-A.E) |(1,5-dibromopentare ONG0 C-OFt 17 J/ CH-C C C-OEt Na 0Et CH-C- - EtOH BY 1-6-v H2O/H CH5 CH-C Hydaoly sis Decetnylation Protonation Co2 HO o ELOH сH ell

) Target Synthesis Na H-C-Oft 60 Na OEt C-CH-C-Oft -EtoH DEE (A.A.E) H ph (phenylethyl bromide CH-C- C -Oft -Oft Na Oft -EtoH ph J CHTB mthar) oft HO/HO Hydreis : De carborylatie n, A- ) Protonato Eton 3- methyl 5-phery) 2 pentanore

9) Target Synthesis 11 NaO Et CH3 -EtoH -C CH- C-OEt -OEt CH CA A.E) HK CH3 (1 No DEt -CH-C-OEt сH CH, -EtoH CHTB CH H,o/H C C св CH-CCC -OEt CH i)DecartorylatiA Pro toation CH -CH CH 3-methyl 2-betanone

4) Tasget Sy nethesis Na OEt OEt Oft -EloH ONao OEt (A A-E) 8 Na 0Et -EtoH oEt oEt Na Det -EtoH LoEt H,/HP Hydra asis - Decadery kte, A Vi) Protonation, Etor

Target oprp Phenyl ketone The above compo end synthesi se frem acetoacetic e ster. Because, the product must containo 3 carbons originate from a cetoacetic ester. CH--CH an't be &in abore Compound, ph eanbear Cant be substituted carbonyl Cc=0) nean 6) Target:- Cyclo buty ethyl ketone Synthes's Nao0ft Br o Et - Eto H -Bs AA-E LOEL BY O -ELOH Et CH3-8 Na O Et -ftoA CHTAX Eto

ட் ஒ LoftM/ :YDecartary lation A Pro tomution Cydlabutyl ethy ketone