By Kenneth Berle Wiberg
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Extra info for Laboratory Technique in Organic Chemistry
H H HH * H N * H H H H H H * H H H H H H H * * H H H H H H H H OH H H CH3 CH3 * CO2H * Smith: Study Guide/ Solutions Manual to accompany Organic Chemistry, Third Edition 1. 63 In shorthand or skeletal drawings, all line junctions or ends of lines represent carbon atoms. Convert by writing in all C’s, and then adding H’s to make the C’s tetravalent. a. H H H C CH3 C C H H HO H C H CH3 C C H CH3 C H H menthol (isolated from peppermint oil) CH3 H H b. CH3 C C C H C C C H H H H C H H H O C H H H H H N CH3 C C C C N C C CH3 H H HH H H C H H H OH c.
4C) Types of water-soluble compounds: • Ionic compounds • Organic compounds having 5 C’s, and an O or N atom for hydrogen bonding (for a compound with one functional group). Types of compounds soluble in organic solvents: • Organic compounds regardless of size or functional group. 88)) • Nucleophiles react with electrophiles. • Electronegative heteroatoms create electrophilic carbon atoms, which tend to react with nucleophiles. • Lone pairs and bonds are nucleophilic sites that tend to react with electrophiles.
3). 7 lower pKa = stronger acid 33 34 Smith: Study Guide/ 2. 3). 4). H C C H + NH2 + H C C NH3 pKa = 38 weaker acid pKa = 25 stronger acid Equilibrium favors the products. 4). 8 CH3COO— CH3CH2O–H 16 CH3CH2O— These bases HCCH 25 HCC— can deprotonate H–H 35 H — CH3COO–H. 5A) The acidity of HA increases both across a row and down a column of the periodic table. C H N H O H H F Increasing electronegativity Increasing acidity H F H Cl H Br Increasing size Increasing acidity H I Smith: Study Guide/ Solutions Manual to accompany Organic Chemistry, Third Edition 2.
Laboratory Technique in Organic Chemistry by Kenneth Berle Wiberg