The dichloride shown (configuration not specified) is heated with excess $NaI$ in dry acetone until both chlorine atoms are replaced by iodine. Counting enantiomers separately, how many stereoisomers does the constitution of the product have? Answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 3

Finkelstein exchange of both chlorines gives 2,3-diiodobutane. It has two identical stereocentres in a symmetric skeleton, so there are the (R,R) and (S,S) enantiomers and one meso form: 3 stereoisomers (RDKit enumeration gives 3, not the

2^{2} = 4

of an unsymmetrical case).

Practice Haloalkanes and Haloarenes More on KCN vs AgCN, KNO2 vs AgNO2, Finkelstein and Swarts on drawn halides

Previous questionNext question

More questions on KCN vs AgCN, KNO2 vs AgNO2, Finkelstein and Swarts on drawn halides

The bromide shown is treated with KCN in aqueous ethanol and the product is then boiled with dilute HCl. Which structure is the final organi... JEE Main level
The bromide shown is heated with AgCN and the product is reduced with H2 over Ni. Which structure is the final product? JEE Advanced level
The bromide shown is converted to compound X as follows: (i) AgNO2, (ii) Sn/HCl, (iii) CHCl3 with alcoholic KOH, heat. Which single reagent,... JEE Advanced level
The compound shown is P. Q is 1-chlorobutane, R is chlorobenzene and S is 2-chloro-2-methylpropane. Arrange them in decreasing order of reac... JEE Advanced level
The bromide shown is treated with different reagents. Following the textbook convention, select all correct statements. JEE Advanced level
The halide shown is treated with the reagent named in each option, and the structure drawn is claimed to be the main product. Select all opt... JEE Main level

The dichloride shown (configuration not specified) is heated with excess NaI in dry acetone until both chlorine atoms are replaced by iodine. Counting enantiomers separately, how many stereoisomers does the constitution of the product have? Answer as an integer.

Answer: 3

More questions on KCN vs AgCN, KNO2 vs AgNO2, Finkelstein and Swarts on drawn halides

The dichloride shown (configuration not specified) is heated with excess $NaI$ in dry acetone until both chlorine atoms are replaced by iodine. Counting enantiomers separately, how many stereoisomers does the constitution of the product have? Answer as an integer.