Please draw out the structure of compounds A-D. Four compounds A, B, C and D have same molecular formula. All the compound could be hydrogenated to produce pentane, and all of the compounds could undergo clectrophilic addition with 2 equivalent of HBr. Only compound A can reaction with copper ammonia(Cu(NO3)+) solution to form red-brown solid. Only compound B could undergo Diels-Alder reaction with alkene. The oxidation of compound C with KMN04 release CO2. The products in the oxidation of compound D with KMNO4 are two different carboxylic acids.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter14: Conjugated Compounds And Ultraviolet Spectroscopy
Section14.SE: Something Extra
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4. Please draw out the structure of compounds A-D.
Four compounds A, B, C and D have same molecular formula. All
the compound could be hydrogenated to produce pentane, and all
of the compounds could undergo electrophilic addition with 2
equivalent of HBr. Only compound A can reaction with copper
ammonia(Cu(NO3)+) solution to form red-brown solid. Only
compound B could undergo Diels-Alder reaction with alkene. The
oxidation of compound C with KMNO4 release CO2. The products
in the oxidation of compound D with KMN04 are two different
carboxylic acids.
Transcribed Image Text:4. Please draw out the structure of compounds A-D. Four compounds A, B, C and D have same molecular formula. All the compound could be hydrogenated to produce pentane, and all of the compounds could undergo electrophilic addition with 2 equivalent of HBr. Only compound A can reaction with copper ammonia(Cu(NO3)+) solution to form red-brown solid. Only compound B could undergo Diels-Alder reaction with alkene. The oxidation of compound C with KMNO4 release CO2. The products in the oxidation of compound D with KMN04 are two different carboxylic acids.
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