Chap 19 Carboxylic Acid

Chap 19 Carboxylic Acid - Chemistry 140C Winter 2010 (K....

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Chemistry 140C Winter 2010 (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? 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.
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Chemistry 140C Winter 2010 (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 you 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 Winter 2010 (K. Albizati) 3 As usual, many of the common low molecular weight carboxylic acids have common names that have caught on over the years and persist to this day. . Important ones in science and in everyday life: Important dicarboxylic acids: Nomenclature Examples: Audience Participation Time!
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Chemistry 140C Winter 2010 (K. Albizati) 4 Structure and Physical Properties The carbonyl group is sp 2 -hybridized and trigonal planar, as you would suspect, with all bond angles around it being about 120 o . R O O H 1.20 A 1.34 A However, the C-O bond lengths are not what you would expect. The carbonyl is a little longer than a typical aldehyde or ketone and the C-O single bond is a little shorter. Resonance structures can explain this: There is a lot of double bond character between the hydrogen-bearing oxygen and carbonyl carbon and a lot of single bond character between carbonyl carbon and carbonyl oxygen. Because it is such a polar functional group, carboxylic acids have relatively high MP’s and BP’s compared to the corresponding aldehydes and ketones. Also, carboxylic acids form hydrogen-bonded dimers in the solid state and in dilute non-aqueous solutions: C O O R H C O O R H hydrogen bond
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Chemistry 140C Winter 2010 (K. Albizati) 5 Low molecular weight carboxylic acids have very pungent odors. Think about vinegar, which contains a high percentage of acetic acid.
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This note was uploaded on 02/18/2010 for the course CHEM 140C 674224 taught by Professor Albizati during the Spring '10 term at UCSD.

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Chap 19 Carboxylic Acid - Chemistry 140C Winter 2010 (K....

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