Solutions for Problem Set 18 - Ethers and Epoxides - Spring 2010 |, Assignments of Organic Chemistry

Download Solutions for Problem Set 18 - Ethers and Epoxides - Spring 2010 | and more Assignments Organic Chemistry in PDF only on Docsity! Problem Set 18_Ethers and Epoxides 2010 Spring CHE 311 1. What is the product of Claisen rearrangement of the 2-butenyl phenyl ether shown below? 2. Choose the best reagent for carrying out the following reactions from the list below. Place the letter of the reagent(s) in the box over the reaction arrow. Use only one letter per box. A. NaH, then CH3I B. NaOCH3, CH3OH C. m-ClC6H4CO3H D. CH3MgBr in ether, then H3O+ E. warm H2SO4/H2O F. Hg(O2CCF3)2, CH3OH G. H2/Pd H. PCC, CH2Cl2 I. Cl2, H2O J. LiAlH4 in ether, then H3O+ 3. Complete the synthetic sequence below by drawing the structures of the reaction in the boxes provided. O CH3 OH OCH3 H CH3 O CH3 CH3 OH CH3 OOH Br2 H2O NaOH NaOCH3 CH3OH PCC CH2Cl2 C8H14O2 Problem Set 18_Ethers and Epoxides 2010 Spring CHE 311 4. Propose a synthesis for the following compound using benzene or toluene and any other reagents necessary. Show all major intermediate compounds that would probably be isolated during the course of your synthesis. 5. Safrole, a substance isolated from oil of sassafras, is used as a perfumery agent. (1) Propose a synthesis of safrole from catechol (1,2-benzenediol). (2) Write the complete stepwise mechanisms for each and every synthetic steps involved in your synthesis. O O Safrolecatechol (1,2-benzene diol) OH OH step(s) H O