MiniQuiz 3 Problem: Draw a rough (but clear) H-NMR of a sample that contains (only)  -monobromoethyl benzene in CCl 4

Lab Lectures: Today, March 2: Conclusion of “Esterification” Grignard reactions MiniQuiz Next Tuesday, 3/9: Conclusion of Grignard. TLC. MiniQuiz Following Tuesday 3/16: Practice. Introduction to Unknowns. Midterm: Tuesday, 3/16, 2:10 – 4pm in your lab (5 Problems. Total: 100 Pts.) Do Sample Midterm (in eres…)! Review/study labs with calculations and problems and our lab lectures.

Methyl Benzoate Synthesis an equilibrium reaction! k equ = 3.0

1.What are the advantages of "boiling under reflux”? 2.What was the purpose of each of the following extraction steps: 1. rinsing with water 2. then extracting with sodium bicarbonate solution 3. extracting with sat. sodium chloride solution? 3.In our extraction with ether, which was the organic layer, top or bottom? 4. What would the H-NMR of methyl benzoate look like? Our Esterification Procedure

Grignard Reaction Grignard Lab postponed to Tuesday Give a definition of "Grignard reagents". Which products do you obtain from the reaction of a Grignard reagent with a carbonyl group followed by hydrolysis? from an aldehyde from a ketone from an ester… ? What type of a reaction is it ….?

Victor Grignard found that, in the presence of ether, magnesium reacts with alkyl and aryl halides at room temperature to form organomagnesium compounds. For this discovery he was awarded the 1912 Nobel Prize in Chemistry (shared with Paul Sabatier, discoverer of catalytic hydrogenation).

RMgX – Ether Complex

Chlorophyll a Grignard reagents are metal-organic compounds. Other examples of metal-organic compounds? Are there any in nature?

Grignard done next week, Tu, Th Our multistep synthesis of triphenyl methanol, starting with the synthesis of our Grignard reagent: Grignard Adduct

Write the structure of the product obtained if our Grignard reagent reacts with a) water b) methanol c) benzoic acid d) carbon dioxide e) acetone f) formaldehyde

Next Tuesday’s Lab lecture: Conclusion of Grignard. TLC MiniQuiz!

MiniQuiz 4 Problem: Write the structure of a diene that would be very reactive in a Diels-Alder reaction: Write the structure of a diene that would NOT react in a Diels-Alder reaction: