Indane can undergo free-radical chlorination at any of the alkyl positions on the aliphatic ring.
(a) Draw the possible monochlorinated products from this reaction.
(b) Draw the possible dichlorinated products from this reaction.
(c) What instrumental technique would be most helpful for determining how many products are formed, and how many of those products are monochlorinated and how many are dichlorinated?
(d) Once the products have been separated, what instrumental technique would be most helpful for determining the structures of all the dichlorinated products?
Indane can undergo free-radical chlorination at any of the alkyl positions on the aliphatic ring. The structure of Indane is,
(a)Here we have to draw the possible monochlorinated products:-
(Indane) (1-chloroindane) (2-chloroindane)
Indane on chlorination in presence of sunlight gives two possible monochlorinated products i.e 1-chloroindane and 2-chloroindane.
(b)The possible dichlorinated products of Indane:-
(Indane) (1,3-dichloroindane) (1,2-dichloroindane) (1,1-dichloroindane) (2,2-dichloroindane)
(1st structure) (2nd) (3rd) (4th)
Indane on chlorination (excess chlorine) in presence of sunlight (h) gives the above possible dichlorinated products.
(c) The above mixture can be separated by gas chromatographic technique but from GC we can not get any structural information. The structural information of a molecule can be obtained from mass spectroscopy. Thus some GC instruments have a mass spectrometer as the detector. After the separation of the samples by GC , the peaks will come and they go directly into the detector ( mass spectrum) , a mass spectrum is collected for each GC peak. The GC-MS will distinguish the monochloro from the dichloro isomers.
(d)Once the products have been separated, the structure of all the chlorinated products can be detect from NMR spectroscopy. In HNMR, a Cl-C-H would appear at a chemical shift =4 (if not benzylic) and =5...