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PHENANTHRENE

This document is a presentation on phenanthrene by Dr. Sumanta Mondal from March 2020. It discusses the structure and properties of phenanthrene, including that it is composed of three fused benzene rings and appears as a white powder with blue fluorescence. It also covers the Haworth phenanthrene synthesis and reactions of phenanthrene, including electrophilic addition versus substitution. The document compares the aromatic character and resonance energies of naphthalene, anthracene, and phenanthrene.

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94 views4 pages

PHENANTHRENE

This document is a presentation on phenanthrene by Dr. Sumanta Mondal from March 2020. It discusses the structure and properties of phenanthrene, including that it is composed of three fused benzene rings and appears as a white powder with blue fluorescence. It also covers the Haworth phenanthrene synthesis and reactions of phenanthrene, including electrophilic addition versus substitution. The document compares the aromatic character and resonance energies of naphthalene, anthracene, and phenanthrene.

Uploaded by

Keval
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
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See discussions, stats, and author profiles for this publication at: https://www.researchgate.

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PHENANTHRENE

Presentation · March 2020


DOI: 10.13140/RG.2.2.24277.78568

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Dr Sumanta Mondal
GITAM (Deemed to be University)
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 PHENANTHRENE
 Phenanthrene is a polycyclic aromatic hydrocarbon composed of three fused benzene rings.
 In its pure form, it is found in cigarette smoke and is a known irritant, photosensitizing skin to light.
 Phenanthrene appears as a white powder having blue fluorescence.
 Phenanthrene is the backbone of morphinan.

 Haworth Phenanthrene Synthesis:

Lecturer Notes_Dr. Sumanta Mondal_B.Pharm-II Sem._ Pharmaceutical Organic Chemistry-I _GITAM UNIVERSITY
1
 Reactions of Phenanthrene

 Aromatic character of naphthalene, anthracene and phenanthrene

 Resonance energy of A = 61 kcal mol-1


 Resonance energy of B = 84 kcal mol-1
 Resonance energy of C = 92 kcal mol-1
 Resonance energy of benzene = 36 kcal mol-1

Lecturer Notes_Dr. Sumanta Mondal_B.Pharm-II Sem._ Pharmaceutical Organic Chemistry-I _GITAM UNIVERSITY
2
 Reactions Phenanthrene (Electrophilic addition versus electrophilic substitution)

 Reactions of anthracene (Electrophilic addition versus electrophilic substitution)

 The reactivity of the 9- and 10-positions toward electrophilic attack, whether reaction leads to substitution or
addition, is understandable since the initially formed carbocation is the most stable one, in which aromatic
sextets are preserved in two of the three rings.
 This carbocation can then either (a) give up a proton to yield the substitution product, or (b) accept a
nucleophile to yield the addition product.
 The tendency for these compounds to undergo addition is due to the comparatively small sacrifice in
resonance energy (12 kcal/ mol for anthracene, 20 kcal/ mol or less for Phenanthrene).

Lecturer Notes_Dr. Sumanta Mondal_B.Pharm-II Sem._ Pharmaceutical Organic Chemistry-I _GITAM UNIVERSITY
3

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