Please answer PRELAB QUESTIONS 1-4 Me O N CO H Me PEG-400 O2N H (rac) proline o

Question

Please answer PRELAB QUESTIONS 1-4

Me O N CO H Me PEG-400 O2N H (rac) proline o Me OH Me n> 8-9 Dime done Me Me Figure 1. Reaction Scheme. Prelab Questions 1) The Material Safety Data Sheets (MSDS) for all the chemicals involved in this lab are on iLearn. Read these and answer the following questions: a) Which chemical is the most dangerous in this lab? b) Explain why you chose your answer for part a), and the safety precautions you will take when handling this material. 2) Fill in the reaction table below. Make sure you correctly calculate the molar amounts of your reactive materials formula mol -eq. Mw mmol name amount p-Nitrobenzaldehyde 151 mg Dimedone 280 mg (t) Proline 57 mg PEG-400 2.0 mL product Page 128 Spring 2017 Chem 12C Lab Manual 3) Calculate the Theoretical Yield of your product, ie. the mass you would expect to recover (assuming 100% conversion to product). 4) We use racemic proline for this reaction, mainly for cost reasons single enantiomers are more difficult to isolate and are more expensive than racemic mixtures. Does this matter for the reaction? Would you expect any difference in the reaction if we used pure (S) proline?

Explanation / Answer

1. According to the material safety data sheet available,

a. Dimedone is the more toxic material

b. Dimedone compared to others are having known lowest acute oral toxicity apart from being an irritant and is thus the most hazardous chemical of all. The other reactants are irritant and have higher acute oral toxicity levels.

2. Reactant and product table

                                            Formula            FW            mol-eq             mmol             amount (mg)  

4-nitrobenzaldehyde          C7H5NO3         151               1.0                  1.0                     151

Dimedone                          C8H12O2          140               2.0                  2.0                     280   

(+/-)-proline                        C5H9NO2         115               0.5                  0.5                      57

PEG-400                                   -                    -                   -                     -                       2.0 mL

Product                            C23H27NO6       413               1.0                  1.0                     413

3. Theoretical yield of the product,

= strating material = 1.0 mmol

= 1.0 mmol x 413 g/mol

= 413 mg

4) No the product has no effect on using chiral or racemic proline for the reaction.

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