Scribd
Upload
6 views24 pages

Phenylacetaldehyde Reactions Overview

The document discusses various organic chemistry reactions involving phenylacetaldehyde, including aldol condensation, Grignard reactions, and Mitsunobu reactions. It also covers concepts like oxidation, alcohol protection and deprotection, and the calculation of Hydrogen Deficiency Index (HDI). Additionally, it mentions specific reactions such as Negishi coupling and olefin metathesis, highlighting their relevance in synthetic pathways.

Uploaded by

deymoupiya07
Copyright
© All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
6 views24 pages

Phenylacetaldehyde Reactions Overview

The document discusses various organic chemistry reactions involving phenylacetaldehyde, including aldol condensation, Grignard reactions, and Mitsunobu reactions. It also covers concepts like oxidation, alcohol protection and deprotection, and the calculation of Hydrogen Deficiency Index (HDI). Additionally, it mentions specific reactions such as Negishi coupling and olefin metathesis, highlighting their relevance in synthetic pathways.

Uploaded by

deymoupiya07
Copyright
© All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd

phenylacetaldehyde

Aldol condensation
anion Z
Similar to nucleophilic acyl substitution
No useful info
1) Grignard reaction
2) Nucleophile attack (SN2) Oxidation Not reduced by LiAlH4

Aldehyde

Alcohol

Alkyne
Mitsunobu
reaction
SN2 (not Grignard)
Not reduced by LiAlH4
Oxidation
Aldehyde

HDI equals , , numerator , 12 times 2 plus 2 , minus open paren 15 plus 1 close paren end numerator , over 2 equals 5

12 × 2 + 2 − (15 + 1)
HDI = =5
2

A ring or a pi bond
4 , cap H cap D cap I.

4 𝐻𝐷𝐼 1 𝐻𝐷𝐼
Not reduced by LiAlH4
Oxidation
Aldehyde

𝐻𝐷𝐼 = 5 𝐻𝐷𝐼 = 5 𝐻𝐷𝐼 = 6

+ ring /
pi bond

1) Oxidation
2) Ring formation
Not reduced by LiAlH4
Oxidation
Aldehyde

𝐻𝐷𝐼 = 5 𝐻𝐷𝐼 = 5 𝐻𝐷𝐼 = 6


Not reduced by LiAlH4
Oxidation
Aldehyde

𝐻𝐷𝐼 = 5 𝐻𝐷𝐼 = 5 𝐻𝐷𝐼 = 6


Parikh–Doering oxidation
Mitsunobu reaction
Mitsunobu reaction (cont.)
Alcohol deprotection (SN2)
Alcohol
protection (SN2)
Swern oxidation

Aldehyde

bicyclic

Alkyne
Olefin
metathesis
tricyclic
Alcohol deprotection (SN2)
Alcohol
protection (SN2)
Swern oxidation

Aldehyde
Negishi coupling

bicyclic

Olefin
metathesis
HDI = 5

tricyclic

HDI = 6
Olefin Metathesis
Olefin Metathesis
bicyclic

Reduction Methylation

tricyclic

HDI = 6

You might also like