Aside from the specified main starting material, only the following compounds can be used as sources of the carbon backbone for the target compound:acetaldehydeethanolpropanoic acidacetic acidethyl bromoacetatepropan-1-olbenzene(2E,4E)-hexa-2,4-dienepropan-2-olbuta-1,3-dienemethanolpropan-2-one (acetone)(chloromethyl)benzene (benzyl chloride)5-methyloxolan-2-onesodium cyanide1-(chloromethyl)-4-methylbenzenephenylacetaldehydesodium methoxidediethyl propanedioate (diethyl malonate)piperidinesodium ethoxideThere are no restrictions with regards to the use of other reagents such as catalysts, solvents, redox agents, protection/deprotection agents, etc. as long as they will not be used as sources of carbon for the skeleton of the target compound.Design a retrosynthetic map and from it, propose a multi-step synthetic approach for the preparation of the target compound from the specified starting material.Write both the retrosynthesis and synthesis plan with brief explanation Target compound:Main starting material:

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Answered: Target compound: Main starting…

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 21.49P

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Aside from the specified main starting material, only the following compounds can be used as sources of the carbon backbone for the target compound:

acetaldehyde	ethanol	propanoic acid
acetic acid	ethyl bromoacetate	propan-1-ol
benzene	(2E,4E)-hexa-2,4-diene	propan-2-ol
buta-1,3-diene	methanol	propan-2-one (acetone)
(chloromethyl)benzene (benzyl chloride)	5-methyloxolan-2-one	sodium cyanide
1-(chloromethyl)-4-methylbenzene	phenylacetaldehyde	sodium methoxide
diethyl propanedioate (diethyl malonate)	piperidine	sodium ethoxide

There are no restrictions with regards to the use of other reagents such as catalysts, solvents, redox agents, protection/deprotection agents, etc. as long as they will not be used as sources of carbon for the skeleton of the target compound.
Design a retrosynthetic map and from it, propose a multi-step synthetic approach for the preparation of the target compound from the specified starting material.
Write both the retrosynthesis and synthesis plan with brief explanation

Target compound:
Main starting material:

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Target compound: Main starting material: OH