Can you explain the mechanism? And can you give any shortcut to use on tbe test Cyclic Acetals are Useful Protecting Groups in Syntheric Organic Chemistry:Ethlene glycol/1,2-ethane diol form CYCLIC ACETALS with CARBONYL group under acidic conditions (reversible process). Cacetals are stable under basic conditions. Cylic acetals open up under acidic conditions.} O:cyclohexanoneexample:OH*catalystO?H:00ОН4-oxo-pentanal(aldehyde-morereactive than ketone)HOOHweaknucleophileShow the mechasimfor hydrolysis!O4-hydroxypentanalОНOH- ОНH* transferThis can be hydrolyzedback to cyclohexanoneand ethylene glycolOH₂O*0+(Hydrolysis)-0OH2HOH*COH₂OH-H₂O-OHO(i) NaBH4(ii) H₂O(Reduction)-H*HO+Hcyclic acetal;aldehyde protected

Consider the mechanism divided into steps as follows:

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Science

Chemistry

Can you explain the mechanism? And can you give any shortcut to use on tbe test

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

Chapter10: Alcohols

Section: Chapter Questions

Problem 10.52P: Alcohols are important for organic synthesis, especially in situations involving alkenes. The...

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Concept explainers

Alkanes and Cycloalkanes

Alkanes are saturated organic compounds which are made up of C and H atoms. Alkanes have the general formula of CnH2n+2. Alkane contains sp3 hybridized carbon atoms with four sigmas (σ) bonds & every hydrogen atom is connected with one of the carbon atoms. The size of the alkane could be determined by the number of carbon atoms located in it.

Question

Can you explain the mechanism? And can you give any shortcut to use on tbe test

Cyclic Acetals are Useful Protecting Groups in Syntheric Organic Chemistry:
Ethlene glycol/1,2-ethane diol form CYCLIC ACETALS with CARBONYL group under acidic conditions (reversible process). C
acetals are stable under basic conditions. Cylic acetals open up under acidic conditions.
} O:
cyclohexanone
example:
O
H*
catalyst
O
?
H
:00
ОН
4-oxo-pentanal
(aldehyde-more
reactive than ketone)
HO
OH
weak
nucleophile
Show the mechasim
for hydrolysis!
O
4-hydroxypentanal
ОН
O
H
- ОН
H* transfer
This can be hydrolyzed
back to cyclohexanone
and ethylene glycol
O
H₂O*
0+
(Hydrolysis)
-0
OH
2
HO
H*
COH₂
OH
-H₂O
-OH
O
(i) NaBH4
(ii) H₂O
(Reduction)
-H*
HO
+
H
cyclic acetal;
aldehyde protected

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