310-29 - CH 310 N LECTURE 29 Textbook Assignment: Chap 21...

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1 CH 310 N LECTURE 29 Textbook Assignment: Chap 21 Benzene & Aromaticity Homework (for credit): POW 9 posted (Due Apr 4) Today’s Topics: Nomenclature & Acidity of phenols Notice & Announcements: “Perspectives on Medicine” Today 2-2:50 WEL 1.308 Adam Horvit, MD - Neurologist Holli Temple, PharmD - Pharmacy 2 Benzene & Benzene & Aromaticity Aromaticity Chapter 21
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3 Cyclopentadienyl Cyclopentadienyl Anion Anion • To convert cyclopentadiene to an aromatic ion, it is necessary to convert the CH 2 group to a CH group in which carbon becomes sp 2 hybridized and has 2 electrons in its unhybridized 2 p orbital: H H H H H the origin of the 6 pi electrons in the cyclopentadienyl anion Cyclopentadienyl anion (aromatic) H H H H H : H H H H H 4 •The p K a of cyclopentadiene is 16 – in aqueous NaOH, it is in equilibrium with its sodium salt – it is converted completely to its anion by very strong bases such as NaNH 2 , NaH, and LDA p K a 15.7 p K a 16.0 Na + + H 2 O H H H H H CH 2 + NaOH : Cyclopentadienyl Cyclopentadienyl Anion Anion
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5 Nomenclature Nomenclature -Monosubstituted Monosubstituted • Monosubstituted alkylbenzenes are named as derivatives of benzene – many common names are retained Toluene Cumene Ethylbenzene Styrene Phenol Aniline Benzoic acid Anisole COOH NH 2 OCH 3 OH Benzaldehyde CHO (commit to memory) 6 Benzyl and phenyl groups: (Z)-2-Phenyl- 2-butene 4-(3-Methoxyphenyl)- 2-butanone
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This note was uploaded on 04/24/2011 for the course CH 56255 taught by Professor Colapret during the Spring '11 term at University of Texas at Austin.

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310-29 - CH 310 N LECTURE 29 Textbook Assignment: Chap 21...

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