Deduce the structures of compound A,B,C and D

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
Chapter21: Benzene And The Concept Of Aromaticity
Section: Chapter Questions
Problem 21.48P: In the chemical synthesis of DNA and RNA, hydroxyl groups are normally converted to triphenylmethyl...
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Deduce the structures of compound A,B,C and D
When the diol shown below is treated with excess PCC, Compound A (C7H1002) is formed as the major product. A gives a positive Tollens' test.
When A is treated with 1 equivalent of ethylene glycol with a catalytic amount of H2SO4 present, Compound B (C9H1402) is the major product. B gives a negative Tollens' test.
When B is with methyl magnesium bromide, followed by a workup with aqueous acid, Compound C (C8H1402) and ethylene glycol are the major organic products. C gives a
positive Tollens' test.
When C is heated with H2NNH2 and KOH, Compound D (C8H160) is isolated as the major organic product. D gives a negative Tollens' test.
Transcribed Image Text:When the diol shown below is treated with excess PCC, Compound A (C7H1002) is formed as the major product. A gives a positive Tollens' test. When A is treated with 1 equivalent of ethylene glycol with a catalytic amount of H2SO4 present, Compound B (C9H1402) is the major product. B gives a negative Tollens' test. When B is with methyl magnesium bromide, followed by a workup with aqueous acid, Compound C (C8H1402) and ethylene glycol are the major organic products. C gives a positive Tollens' test. When C is heated with H2NNH2 and KOH, Compound D (C8H160) is isolated as the major organic product. D gives a negative Tollens' test.
ОН
НО
OH
HO,
excess PCC
(1 equiv.)
H2SO4 (cat.)
A (C,H1,02)
B (C,H1403)
1) CH,MgBr
H,NNH,
2) H,0*
Кон, heat
C (C3H1402)
D (C3H160)
+
HO
OH
For the toolbar, press ALT+F10 (PC) or ALT+EN+F10 0M
Transcribed Image Text:ОН НО OH HO, excess PCC (1 equiv.) H2SO4 (cat.) A (C,H1,02) B (C,H1403) 1) CH,MgBr H,NNH, 2) H,0* Кон, heat C (C3H1402) D (C3H160) + HO OH For the toolbar, press ALT+F10 (PC) or ALT+EN+F10 0M
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