Selecting Solvents for Reactions

In many questions about chemical reactions the solvent is often ignored. This question asks you to consider the suitability of certain common solvents for use in a specified reaction. Focus on reactivity problems rather than solubility issues.

Choose one of the twelve following reactions by clicking on its radio button.

  Reaction of thionyl chloride (SOCl2) with (CH3)2CHCH2OH to form (CH3)2CHCH2Cl.
  Addition of Br2 to CH3CH2CH2CH=CH2 to form CH3CH2CH2CHBrCH2Br.
  E2 elimination of cyclohexylbromide to cyclohexene by treatment with hot KOH. 
  Formation of the Grignard reagent (CH3)2CHCH2MgBr from (CH3)2CHCH2Br by reaction with Mg.
  Aldol reaction of CH3CH2CH2CH=O by treatment with NaOH.
  Fischer esterification of CH3CH2CO2H with (CH3)2CHCH2OH by heating with a strong acid catalyst.
  Conversion of CH3CH2CH2CH2OH to CH3CH2CH2CH2I by heating with conc. HI.
  Diels-Alder cycloaddition of CH2=CH–CH=CH2 with CH2=CH–C≡N
  Williamson ether formation by reaction of (CH3)2CHCH2O(–)K(+) with CH3CH2CH2CH2Br.
  Reaction of sodium acetylide (HC≡CNa) with CH3CH2CH2Br to give CH3CH2CH2C≡CH.
  Acetylation of C6H5CH2OH with (CH3CO)2O (pyridine catalyst) to give C6H5CH2OCOCH3.
  Formation of a Wittig reagent by reaction of (C6H5)3PCH3(+) Br(–) with n-butyl lithium (CH3CH2CH2CH2Li).

Once the problem is selected check all the following solvents that would be unsuitable for that reaction. (simply click the box beneath the name).

Common Solvents
Water
 Ethanol
 Acetone
 Ethyl Acetate
 Chloroform
 Acetonitrile
 Ether
 THF
Hexane
 Benzene





This script written by William Reusch, Dept. of Chemistry, Michigan State University. Please send comments and corrections to whreusch@pilot.msu.edu.