Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter H, Problem 4PP

Practice Problem H.4

In 1891 G. Merling transformed tropine (see Practice Problem H.3) into 1,3,5-cycloheptatriene (tropylidene) through the following sequence of reactions:

Tropine ( C 8 H 15 NO ) H2O C 8 H 13 N CH 3 I C 9 H 16 NI ( 2 ) heat ( 1 ) Ag 2 O/H 2 O C 9 H 15 N CH 3 I C 10 H 18 NI ( 2 ) heat ( 1 ) Ag 2 O/H 2 O 1,3,5-cycloheptatriene + ( CH 3 ) 3 N + H 2 O

Write out all of the reactions that take place.

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