Lecture5CHM233(10)final

Lecture5CHM233(10)final - Organic Chemistry, Third Edition...

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1 Organic Chemistry , Third Edition Janice Gorzynski Smith University of Hawai’i Chapter 2
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Which species behave as bases in the following reaction? H 2 SO 4 + HNO 3 HSO 4 + H 2 NO 3 + 1 2 3 4 A)3 and 4 B)2 and 3 C)2 and 4 D)1 and 3 E)1 and 2 !
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3 Acidity of Some Common Compounds
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4 Hybridization Effects Consider the relative acidities of three different compounds containing C–H bonds.
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5 Stability of Conjugate Bases The higher the percent of s -character of the hybrid orbital, the more stable the conjugate base.
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C C O H H H H H H C C O H H H H H H C C N H H H H H H H C C H H H C C H H A B C D E H !
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7 Figure 2.5 Summary of Factors that Determine Acid Strength
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8 Commonly Used Acids in Organic Chemistry The familiar acids HCl and H 2 SO 4 are often used in organic reactions. Various organic acids are also commonly used (e.g.,acetic acid and p -toluenesulfonic acid (TsOH)).
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9 Common strong bases used in organic reactions are more varied in structure. Commonly Used Bases in Organic Chemistry Figure 2.6
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10 Strong bases have weak conjugate acids with high p K a values, usually > 12. Strong bases have a net negative charge, but not all negatively charged species are strong bases. For example, none of the halides F ! , Cl ! , Br ! , or I ! , is a strong base. Carbanions, negatively charged carbon atoms, are especially strong bases. A common example is butyllithium. Characteristics of Strong Organic Bases
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11 Acidity of Some Common Compounds
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12 Amines (e.g., triethylamine and pyridine) are organic bases. They are basic due to having a lone pair on N. They are weaker bases since they are neutral, not negatively charged. Other Common Bases in Organic Chemistry
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13 Lewis Acids and Bases A Lewis acid is an electron pair acceptor. A Lewis base is an electron pair donor. Lewis bases are structurally the same as Br Ø nsted-Lowry bases. Both have an available electron pair—a lone pair or an electron pair in a ! bond.
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This note was uploaded on 01/03/2012 for the course CHEM 233 taught by Professor Anamoore during the Fall '10 term at ASU.

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Lecture5CHM233(10)final - Organic Chemistry, Third Edition...

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