5. Compound A and B are isomers of carbonyl groups with the molecular formula of CH,O. both compound A and B give positive result towards the Tollen's reagent and iodoform test respectively. Upon reaction with LIAIH4, compound B produces a secondary alcohol (compound C). Compound C further reacts with PCI3 and Mg in ether to produce compound D, a Grignard reagent. Compound A undergo an aldol condensation reaction to produce 3- hydroxy-2,2,4-trimethylpentanal. a) Draw the structural formula for compound A, B, C and D. b) Draw the structural formula of the product formed when compound A reacts with compound D. c) State two reagents (other than PCI3) that can be used to convert C to an acyl chloride.

5. Compound A and B are isomers of carbonyl groups with the molecular formula of CH,O. both compound A and B give positive result towards the Tollen's reagent and iodoform test respectively. Upon reaction with LIAIH4, compound B produces a secondary alcohol (compound C). Compound C further reacts with PCI3 and Mg in ether to produce compound D, a Grignard reagent. Compound A undergo an aldol condensation reaction to produce 3- hydroxy-2,2,4-trimethylpentanal. a) Draw the structural formula for compound A, B, C and D. b) Draw the structural formula of the product formed when compound A reacts with compound D. c) State two reagents (other than PCI3) that can be used to convert C to an acyl chloride.

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

Chapter16: Aldehydes And Ketones

Section: Chapter Questions

Problem 16.26P: Wittig reactions with the following -chloroethers can be used for the synthesis of aldehydes and...

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