The reaction of 1-iodopropane with potassium thiocyanate (KSCN) in certain solvents results in the formation of two isomeric products, propylthiocyanate and propylisothiocyanate (see scheme below), via the SN2 reaction mechanism.

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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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The reaction of 1-iodopropane with potassium thiocyanate (KSCN) in certain solvents results in the formation of two isomeric products, propylthiocyanate and propylisothiocyanate (see scheme below), via the SN2 reaction mechanism.

 

Attempts to prepare a similar mixture of these same isomeric products (propylthiocyanate and propylisothiocyanate) starting from 1-propene is illustrated below. Despite the strong acidity of thiocyanic acid (recall pKa = 1.1), this addition reaction does not lead to either of the products indicated. Based on your knowledge of alkene addition reactions, explain this experimental result. 

CH3CH=CH2
H-SCN
Pr-SCN
Pr-NCS
+
Not observed
(Pr = 1-Propyl)
Transcribed Image Text:CH3CH=CH2 H-SCN Pr-SCN Pr-NCS + Not observed (Pr = 1-Propyl)
Solvent
CH3CH2CH21
K SCN
Pr-SCN
Pr-NCS
+
1-Propylthio-
cyanate
1-Propylisothio-
cyanate
Transcribed Image Text:Solvent CH3CH2CH21 K SCN Pr-SCN Pr-NCS + 1-Propylthio- cyanate 1-Propylisothio- cyanate
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