<p> Dr. Caroline Clower Chemistry 2412 Carboxylic Acids and Derivatives Key</p><p>1. Name the following compounds.</p><p>Cl (a) propanoyl chloride</p><p>O</p><p>O (b) isopropyl acetate O</p><p>N (c) N-ethyl-N-methylacetamide</p><p>O</p><p>O</p><p>(d) C O phenyl benzoate</p><p>CH3</p><p>(e) H (S)-3-hydroxybutanoic acid CH CO H HO 2 2</p><p>O (f) E-2-methyl-2-butenoic acid HO</p><p>(g) 2-ethyl-4-methylhexanoic acid</p><p>CO2H</p><p>O O</p><p>(h) acetic butanoic anhydride O Dr. Caroline Clower Chemistry 2412 Carboxylic Acids and Derivatives Key</p><p>2. Draw structures for the following compounds.</p><p>O (a) Octanoyl chloride</p><p>Cl</p><p>OH O (b) Ethyl 3-hydroxybutanoate</p><p>O</p><p>(c) N-Cyclohexylpentanamide O</p><p>N H</p><p>(d) Propanoic anhydride O O</p><p>O</p><p>(e) Formic propanoic anhydride O O</p><p>H O</p><p>O (f) 2-Pentynoic acid C C</p><p>HO</p><p>O (g) 10-Undecenoic acid</p><p>HO</p><p>CO2H (h) 2-Methylbenzoic acid</p><p>CH3 Dr. Caroline Clower Chemistry 2412 Carboxylic Acids and Derivatives Key</p><p>3. Provide reagents by each arrow below to complete the following reaction scheme.</p><p>Br CO2H CH2OH 1. Mg, Et2O 2. CO2 + 1. LAH, 2. H O+ 3. H3O 3</p><p>H2CrO4</p><p>CO2H CO2CH3 CO2H</p><p>+ - + H2O, H or OH CH3OH, H</p><p>SOCl2</p><p>C(O)Cl CO2H CHO 1. LAH + 2. H3O H2O, pyridine 3. PCC</p><p>N2H4, KOH</p><p>CH2OH CO2H CH3</p><p>+ 1. LAH, 2. H3O KMnO4</p><p>PCC</p><p>CHO CO2H CO2C(O)CH3</p><p>1. SOCl2 H2CrO4 2. CH3CO2Na Dr. Caroline Clower Chemistry 2412 Carboxylic Acids and Derivatives Key</p><p>4. Each of the following conversions requires more than one step. Show reagents and experimental conditions necessary to bring about each conversion.</p><p>O O (a)</p><p>H OCH3</p><p>O O O H2CrO4 CH3OH</p><p>H H2SO4 OH OCH3</p><p>CH3 CH2CO2CH2CH3 (b)</p><p>CH3 CH2Br CH2MgBr Br2 Mg</p><p> h Et2O</p><p>1. CO 2+ 2. H3O</p><p>CH2CO2CH2CH3 CH2CO2H CH3CH2OH</p><p>H+ Dr. Caroline Clower Chemistry 2412 Carboxylic Acids and Derivatives Key</p><p>CH3 O (c) C NO2</p><p>H2N</p><p>Cl</p><p>CH3 CH3 CH3</p><p>Cl Cl HNO3 2</p><p>H2SO4 FeCl3</p><p>NO2 NO2</p><p>- 1. KMnO4, OH ,  2. H+</p><p>CO2H C(O)NH2 C(O)Cl</p><p>Cl Cl Cl SOCl 2 NH3 2</p><p>NO2 NO2 NO2 O</p><p>C Dr. Caroline Clower Chemistry 2412 H3C OH Carboxylic Acids and Derivatives Key</p><p>5. What is the order of decreasing activity (most reactive = 1, least reactive = 4) towards 1 7 nucleophilic acyl substitution for the following carboxylic acid derivatives? 2 3 4 5 6</p><p>O O O O O</p><p>H C C O C CH H C C N(CH ) H C C O CH (CH ) CH C O CH O 3 O 3 O 3 3 2 O 3 3 O 3 2 3 8 9 10 C 1 C C 4 C 2 C 3 H3C Cl H3C O CH3 H3C OCH2CH3 H3C NH2</p><p>11 12 13 14 15 16 17 18 19 20</p><p>6. Draw the major organic products formed from the following reactions or sequences of reactions.</p><p>O O OH OH NH2 C H (a) 1. LiAlH4, ether OH + 2. H3O</p><p>CH3 C Ph</p><p>C Ph CH2OH O O</p><p>O O</p><p>OH OCH3 HCl (b) + CH3OH H2O</p><p>O excess OH MgBr + (c) H3O CH3CH2 C CH2CH2CH3 Cl ether</p><p>CH2CH2CH3</p><p>H N</p><p>+ N SOCl2 LiAlH4 H3O (d) CO2H</p>