Organic chemistry synthesis lab: Lab 10: Fall 2017-Planning an Org 18 points TA:

Question

Organic chemistry synthesis lab: Lab 10: Fall 2017-Planning an Org 18 points TA: anic chemistry lab experiment Name: Due Week of Nov 27 before start of Lab final exam Problem 1: Using any technique and chemical reaction(s) covered in CHE 201 this semester prepare compound B from 5 mmoles of compound A. Compound A is very expensive and your planned reaction needs to be efficient (90 % or higher yield). PART A: 13 points (replaces data sheet, note book, performance and lab report points) 1. Plan and show your planned synthetic schem Properties Mol, weig 214.1 196.6 166 C 348 C377 C 488 C 0.5 e in the 178.2 form of a reaction equation. 3 points 194 C 94 C a detailed procedure (Preparation, PurificationMelting/Freezing Point & Analysis). 10 points Procedure should include quantities (with correct stoichiometry) of chemicals required 1. 0.8 0.02 2. Mention all the techniques that will be required. 10 ml hot water) 3. Name all the glassware required. 4. Provide a data table, it should list all the reagents(grams in 10 ml hexane) Solubility (grams in Solubility Solubility 0.8 0.4 0.44 0.5 and the required quantities needed for the preparation and purification. Provide a flowchart for the planned synthesis. 1.5 (grams in 10 ml ethyl ether) 5. Complete worksheet Attach more sheets of paper as needed PART B: 5 points (replaces pre-lab quiz 10) Using curved arrows to designate the flow of electrons, provide a detailed stepwise mechanism for your planned reaction(s) 11/10/2017 Ahsan-Riaz-CHE 201 Fall 2017-Lab 10-University at Buffalo 3

Explanation / Answer

Organic chemistry synthesis lab

The first step of the given reaction is an acid mediated ring-opening reaction. The reagent used may be HCl (aq) solution. The lactone ring opens with assistance from proton H+ coming from acid added and water present in the reaction. The resulting species may undergo and elimination and substitution to form product B as major product. The species formed in the first step may also to a small extent undergo substtituion at side chain carbon withot any elimination to form product C.

Here B is desired product and C is a side reaction.

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