Indane can undergo free-radical chlorination at any of the

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L. G. Wade Jr

Problem 45SP Chapter 17

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L. G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 45SP

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?

Step-by-Step Solution:
Step 1 of 3

Indane can undergo free-radical chlorination at any of the alkyl positions on the aliphatic ring. The structure of Indane is,

Step-1

(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.

Step-2

(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.

Step-3

(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.

Step-4

(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...

Step 2 of 3

Chapter 17, Problem 45SP is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L. G. Wade Jr
ISBN: 9780321768414

Organic Chemistry was written by and is associated to the ISBN: 9780321768414. The answer to “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?” is broken down into a number of easy to follow steps, and 80 words. The full step-by-step solution to problem: 45SP from chapter: 17 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. Since the solution to 45SP from 17 chapter was answered, more than 781 students have viewed the full step-by-step answer. This full solution covers the following key subjects: products, monochlorinated, dichlorinated, determining, most. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8.

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