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Ch 19 notes - Chemistry 140C Spring 2009(K Albizati Course...

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Chemistry 140C Spring 2009 (K. Albizati) 1 Course Introduction Introduction Participant Survey Course Syllabus Teaching Format and Style Who likes O Chem? Very interactive Style Questions during lecture are important Will be a lot of problem solving during lecture, including audience participation What is Organic Chemistry and why is it important? Old definition – chemistry of compounds from living organisms New definition – chemistry of compounds which contain CARBON Nature has selected this element as the base element of life processes because it is able to form very strong covalent bonds to itself and to other elements. This enables highly complicated compounds, chemical reactions and chemical reaction pathways. Our bodies are just walking bags of chemicals inter-reacting which allow complex events, like locomotion, vision, speech, thought and others to occur. If you want to understand the field of medicine, you must understand biochemistry and Molecular Biology. To understand Biochemistry and Molecular Biology you must have a firm understanding of Organic Chemistry. Reading: V&S Chapter 19; sections to skip: 19.3 (spectroscopy) Problem assignments: V&S Chapter 19 problems; skip problems 19-2, 19-3, 19-26, 19-35, 19-44, 19-46, 19-49
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Chemistry 140C Spring 2009 (K. Albizati) 2 Chapter 19 – Carboxylic Acids The carboxyl group is a key functional group in biochemistry and molecular biology. The oxygens are Lewis basic sites and have slight nucleophilic character and carbonyl carbon is electrophilic. Like all carbonyl groups, carboxyl carbonyls are subject to nucleophilic addition reactions: Probably a good idea to review Chapter 17. Nomenclature Carboxylic acids take precedence in naming functional groups over any functional group we have already seen. The carboxyl group is always at the end of a chain and it is numbered as C1. Order of precedence is on p 857 but is not for memorization. In naming, the suffix –oic acid replaces the –e suffix on alkane names. So…..
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Chemistry 140C Spring 2009 (K. Albizati) 3 As usual many of the common low molecular weight carboxylic acids have common names that have stuck over the years. Important ones in science and in everyday life: Important dicarboxylic acids: OH O oxalic acid (industrial use) HO O COOH terephthalic acid (polymers) HOOC O O HO OH adipic acid (polymers) O HO succinic acid (foodstuffs) OH O Nomenclature Examples: Audience Participation Time!
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Chemistry 140C Spring 2009 (K. Albizati) 4 Structure and Physical Properties Carbonyl group is sp 2 –hybridized and trigonal planar, as you would suspect, with all bond angles around it being about 120 o . However, the C-O bond lengths are not what you would expect. The carbonyl is a little longer than a typical aldehyde and the C-O single bond is a little shorter.
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