Question

For the last step in your potential Nobel-prize winning cancer cure drug you need 3-cyclopentyl-1-phenylhexan-3-ol, but no chemical company sells this particular alcohol. You, being the wonderful synthetic chemist that you are, figure you can make this tertiary alcohol from the simple Grignard reagent reaction you learned in your CH223 course.

A) Draw the structure of your target alcohol. Use the name to make sure you have the correct number of carbons:

B) If the Grignard reagent contains the aromatic ring, draw both the appropriate Grignard reagent and carbonyl compound (not an ester) you would need to make your target molecule. Input the Grignard reagent first, then click the "New" tool to allow the carbonyl compound input.

C) If the Grignard reagent contains the five-membered ring, draw both the appropriate Grignard reagent and carbonyl compound (not an ester) you would need to make your target molecule. Input the Grignard reagent first, then click the "New" tool to allow the carbonyl compound input.


D) There is one more combination that you could use to arrive at the targent alcohol. Input the Grignard reagent first, then click the "New" tool to allow the carbonyl compound (not an ester) input of this last possible synthetic scheme.

Answer 1

Answer – A) The structure of 3-cyclopentyl-1-phenylhexan-3-ol –

B) Grignard reagent contains the aromatic ring, draw both the appropriate Grignard reagent and carbonyl compound to make your target molecule, so there is Grignard reagent contain benzene ring and the substituent with -CH₂-CH₂-MgBr and the 1-cyclopentylbutan-1-one as follow   –

C) Grignard reagent contains the five-membered ring, draw both the appropriate Grignard reagent and carbonyl compound to make your target molecule, so the Grignard reagent contains the five-membered ring with - MgBr and 1-phenylhexan-3-one as follow -

D) There is one more combination that use to arrive at the targent alcohol, so it the 1-cyclopentyl-3-phenylpropan-1-one and Grignard reagent is propyl magnesium bromide as follow –