The procedure of methylation of amines and thermal decomposition of quaternary ammonium hydroxides was first reported by Hofmann in 1851, but its value as a means of structure determination was not appreciated until 1881, when he published a report of its use to determine the structure of piperidine. Following are the results obtained by Hofmann. 1. CHI (excess), К,СО, 2. Ag,O, H,O 3. heat 4. CH3I (excess), K,CO3 5. Ag.O, H,О 6. heat C5H1|N C;H15N CH2=CHCH,CH=CH2 Piperidine (A) 1,4-Pentadiene

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter5: Alkenes: Bonding, Nomenclature, And Properties
Section: Chapter Questions
Problem 5.31P
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Propose two additional structural formulas (excluding stereoisomers) for C5H11N that are also consistent with the results obtained by Hofmann.

The procedure of methylation of amines and thermal decomposition of
quaternary ammonium hydroxides was first reported by Hofmann in 1851, but
its value as a means of structure determination was not appreciated until 1881,
when he published a report of its use to determine the structure of piperidine.
Following are the results obtained by Hofmann.
1. CHI (excess), К,СО,
2. Ag,O, H,O
3. heat
4. CH3I (excess), K,CO3
5. Ag.O, H,О
6. heat
C5H1|N
C;H15N
CH2=CHCH,CH=CH2
Piperidine
(A)
1,4-Pentadiene
Transcribed Image Text:The procedure of methylation of amines and thermal decomposition of quaternary ammonium hydroxides was first reported by Hofmann in 1851, but its value as a means of structure determination was not appreciated until 1881, when he published a report of its use to determine the structure of piperidine. Following are the results obtained by Hofmann. 1. CHI (excess), К,СО, 2. Ag,O, H,O 3. heat 4. CH3I (excess), K,CO3 5. Ag.O, H,О 6. heat C5H1|N C;H15N CH2=CHCH,CH=CH2 Piperidine (A) 1,4-Pentadiene
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