Problem: Select reagents from the table to synthesize this compound from cyclopentanone.A. C6H5CHOB. NaOH, ethanolC. Pyrrolidine, cat. H+ D. H2C=CHCN E. H3O+ D. LDAG. EtOC(=O)CO2Et H. BrCH2CH=CH2 I. Na+ -OEt, ethanol J. Br2, H+ K. K+ t-BuO- L.CH2(CO2Et)2 m. heat

FREE Expert Solution

Reaction steps: 

  1. Bromination of cylopentanone using J. Br2, H+ 
  2. Elimination (E2) reaction using K. K+ t-BuO- 
  3. Addition reaction with diethylmalonate L.CH2(CO2Et)2 
  4. Formation of sodium salt from compound formed in (3) using I. Na+ -OEt, ethanol
  5. Hydrolysis using E. H3O+ 
  6. Heating (m. heat) to eliminate CO2 to get the final product
View Complete Written Solution
Problem Details

Select reagents from the table to synthesize this compound from cyclopentanone.

A. C6H5CHO

B. NaOH, ethanol

C. Pyrrolidine, cat. H+ 

D. H2C=CHCN 

E. H3O+ 

D. LDA

G. EtOC(=O)CO2Et 

H. BrCH2CH=CH2 

I. Na+ -OEt, ethanol 

J. Br2, H+ 

K. K+ t-BuO- 

L.CH2(CO2Et)2 

m. heat

Frequently Asked Questions

What scientific concept do you need to know in order to solve this problem?

Our tutors have indicated that to solve this problem you will need to apply the Substitution/Elimination Retrosynthesis concept. If you need more Substitution/Elimination Retrosynthesis practice, you can also practice Substitution/Elimination Retrosynthesis practice problems.