Exam-3J - EXAM 3 1:4” 2.001 thm‘e33 A NOMENCLATURE(12 points 4 pts each Give an aceeptable IUPAC name for each of the following compounds Be

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Unformatted text preview: EXAM 3/. 1:4” 2.001 thm‘e33 A. NOMENCLATURE: (12 points, 4 pts. each) Give an aceeptable IUPAC name for each of the following compounds. Be sure to indicate the stereochemistry where appropriate. Br HO CH3 H3 B. FACTS (Total 26 points) 1. Place the following alcohols in order of their increasing reactivity in acid-catalyzed dehydration reactions (1 = least reactive, 3 2 most reactive). (3 pts) H 3 H3 H H3 H3 H3 H3 H3 H3 OH OH 2. Place the following alkenes in order of their increasing reactivity in reaction with HCl (1 = least reactive, 3 = most reactive). (3 pts) E El D 3. Check the box(es) below the reactive intermediate(s) that are generated during the reaction of CHC13 with KOH. (3 pts) \/ CI Cl 4. Check the box(es) below the reagent(s) that can be used to produce Grignard reagent. (3 pts) iBr jiA/Br /°\/\O/\/\B, D D E 5. Place the following compounds in order of their increasing boiling points (1 = lowest boiling point, 3 = highest boiling point). (3 pts) D E] D 6. Place the following indicated bonds in order of their increasing bond length (1 = shortest, 4 = longest). (3 pts) NW” D E] D 6. Check the b0x(es) below the reagent(s) that can be used to convert acetylene into aeetylide anion. (5 pts) 0 H3O /H\O® e CH3CH2C HgCHzLi H3C—>—OGK @ NaNH2 CHscHZMgBr H3C K m m at] :1 D 7. Place the following compounds in order of their increasing stability (1 = least stable, 3 = most stable). (3 pts) W W W m E m C. REACTIONS: (42 points, 7 pts. each) Please give the final major product, the starting material, or the reactants for each of the following_reactions in the box provided. Be sure your answers indicate stereochemistry where appropriate. Intermediate products may be placed below the reaction for partial credit but not in the answer box. 1. (CH3)3CO - K+ 1, 2. Br /H O 3. HZSO4/heat Br Br B r CH30H2 CH2CH3 | I \ / 2. CH3'CH'CH'CH3 C = C / \ H H 1. CH3CH20 - Na+ 2. MCPBA/CCI4 3. H30+ 003H NOTE : MCPBA = (:L Cl 1.Na/NH3 4. CHs-CEC‘CHs —————> 2. CHBr3 IKOH 1. SiagBH - CH3 OH 5- 2. H202/OH l l O a CH30HCH2-CH 3. MgBr 4. H30+ (or H20) 1.03 H30\ /CH3 2. (CH3)ZS 6. 0:0 ———> HSC/ \CH3 3. CHaCEC - Na+ 4. H30+ (or H20) D. MECHANISM: (10 points) The following reaction yields a mixture of products. Provide a clear mechanism for the formation of A, B and C. Use curved arrow notation to indicate “electron flow”, and show all intermediates and formal charges. 0 HO CH3 HCI / H20 (solvent) E. Synthesis: 10 Points From cyclohexane, any alkanes, alkenes or alkynes ofmo carbons or less, and any inorganic reagents, synthesize the compound below. Br <:><(13H CH ZCHZCHZCHa Br ...
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This note was uploaded on 11/09/2010 for the course CHEM 2324 taught by Professor None during the Spring '10 term at Lone Star College.

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Exam-3J - EXAM 3 1:4” 2.001 thm‘e33 A NOMENCLATURE(12 points 4 pts each Give an aceeptable IUPAC name for each of the following compounds Be

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