mit-o2-h3-ans

mit-o2-h3-ans - Massachusetts Institute of Technology Dr....

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Massachusetts Institute of Technology 5.13, Fall 2006 Dr. Kimberly L. Berkowski Organic Chemistry II EXAM #3 EXTRA PROBLEMS What to expect on Exam #3: 1. ~1 Labeling experiment 2. ~2 Mechanisms 3. ~2 Syntheses 4. ~5 transformations – supply missing product 5. ~5 transformations – supply missing reagents 6. ~3 General questions KEY
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1. (4 points each, 8 points total) In the boxes, please provide the reagents for the illustrated transformations. More than one step may be required. 2. (2 points each, 8 points total) Please provide the products of the following reactions. If no reaction is expected, write “NR”. NAME____________________________ 1 Figure by MIT OCW. Figure by MIT OCW. O OH i-Pr O H i-Pr O OH i-Pr i-Pr Br (a) (b) 1. KCN 2. H 3 O + or or 1. Mg ,ether 2. CO 2 3. H 3 O + /workup 1. SOCl 2 2. LiAl( OtBu ) 3 H 3. workup 1. LiAlH 4 (XS) 2. H 2 O 3. PCC Et O Et Cl O O Et OH O Et OMe O (a) (b) (c) (d) Et NMe 2 O 1. Excess Na BH 4 2. Workup 2. Workup 1. Excess MeMgBr 2. Workup 1. Excess MeLi 2. Workup 1. Excess LiAlH 4 OH NR or HO Me Me Et Et NMe 2 Et
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3. (2 points each, 16 points total) Please provide the requested products or reagents. If no reaction is expected, write “NR”. Name_________________________ 2 Figure by MIT OCW. NH 2 N 2 Br (d) (c) NH 2 O O n-Bu H 2 O H 3 O + Me Me H 2 N cat. H + (b) 1. LiAlH 4 2. workup Me Me Me Me NH 2 NH 2 H 2 O 2 , Δ (a) Br 2, NaOH N-OH POCl 3 NaNO 2 HCl CuBr O n-Bu NH 2 O OH nBu CN OH
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4. (11 points) Please provide a detailed mechanism for the illustrated conversion of acetic acid ( A ) to acetyl chloride ( B ). Name_______________________ 3 Figure by MIT OCW. OH Me O OH Me Me O O OH Me O Me O Cl Me O O + S Cl Cl O S Cl Cl O S Cl + + + + SO 2 SO 2 HCl B A Cl Cl H Cl OH
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5. (11 points each, 22 points total) Please provide syntheses for
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This note was uploaded on 02/10/2011 for the course CHEM 2420 taught by Professor Staff during the Spring '08 term at Wyoming.

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mit-o2-h3-ans - Massachusetts Institute of Technology Dr....

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