Draw the arrow-pushing mechanism of a generic esterification reaction: (2) From

Question

Draw the arrow-pushing mechanism of a generic esterification reaction:

(2) From the spectral data (NMR, IR, MS) you were given, identify the structure of your ester product. (3) Based on your answer to Q2, what is the structure of your starting alcohol?
(4) Assign the major peaks in the IR spectrum of your product.

(5) Fully assign the 1H NMR spectrum of your product (i.e. determine which peaks in the 1H NMR correspond to which hydrogens in the product). You will not receive full marks for determination of the unknown unless you assign the 1H NMR spectrum completely.

(6) You will notice that we gave you the m/z value of the M+ ion of your product on the EI (electron impact) mass spectrum, but the actual peak on the spectrum is very small (or even non-existent). Read McMurry p426-432 (especially p431) and explain why the M+ peak is so small.

resin to the flask and, followed by 700 L glacial acetic acid. Equip with an air condenser and transfer the flask to a sand bath on a magnetic stirer. NOTE: Glacial Acetic Acid is corrosive and toxic all manipulations should be performed in the fumehood. Heat the reaction to 170 °C for 30 mins, then remove the reaction from the sand bath and allow to cocl to room temperature. 2. Isolation of Product Remove the Nafion strip and spinbar (with tweezers), and carefully rinse them (into the reaction flask) with 1 mL deionized water. Carefully add 3 mL 5% NaHCOs solution to the flask (add dropwise to avoid foaming) and swirl to mix the phases. Transfer to a separatory funnel and add 20 mL diethyl ether. Separate the aqueous phase and place it in a 50 mL Erlenmeyer flask (keep the organic layer in the separatory funnel). Wash the organic layer with 2 x 5 mL portions of 5% NaOH, followed by 2 x 10 mL deionized water, combining the aqueous washes in the Erlenmeyer flask. Transfer the organic layer to a second Erlenmeyer flask, add anhydrous sodium sulfate and leave to dry for 5 mins. Remove the sodium sulfate via gravity filtration. Discard the solid and transfer the solution to a 50mL round-bottomed flask, then remove the solvent via rotary Obtain an IR spectrum of your liquid product and you alcohol starting material. 3. Analysis of your product Your TA will give you a 'H and C NMR and El Mass spectrum of your product. Hand these in with your postlab report. Post Lab Questions In your lab report, MAKE SURE to identify which alcohol you were assigned (A-E) (1) Draw the arrow-pushing mechanism of a generic esterification reaction: 0 +CH3-OH CH3 +H20 (2) From the spectral data (NMR, IR, MS) you were given, identify the structure of your ester product. (3) Based on your answer to Q2, what is the structure of your starting alcohol? (4) Assign the major peaks in the IR spectrum of your product. (5) Fully assign the H NMR spectrum of your product (i.e. determine which peaks in the 'H NMFR correspond to which hydrogens in the product). You will not receive full marks for determination of the unknown unless you assign the 'H NMR spectrum completely. (6) You will notice that we gave you the m/z value of the M* ion of your product on the El (electron impact) mass spectrum, but the actual peak on the spectrum is very small (or even non-existent) Read McMurry p426-432 (especially p431) and explain why the M peak is so small. Page | 18

Explanation / Answer

Draw the arrow-pushing mechanism of a generic esterification reaction: (2) From

Related Questions

Navigate

• Browse (All)
• Browse D
• Subjects

---

---

Integrity-first tutoring: explanations and feedback only — we do not complete graded work. Learn more.