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Organometallic and Grignard Reactions

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There are just a few questions I'd like answered to check my understanding. The questions can be found near the bottom of the page.

Notes for Grignard
- All glassware must be completely dry! (Place the glassware in the oven for 20 minutes to dry. It is not necessary to flame-dry. Lightly grease the ground joints before placing the glassware in the oven. After drying, assemble the glassware while it is still hot.
- Plan to add 1 or 2 crystals of iodine, no more than that, prior to beginning to add 2-bromopentane to the magnesium. You will receive additional instructions for initiating the reaction from your AI.
- You will perform this reaction at ½ scale.

3. How might primary, secondary, and tertiary alcohols be prepared from a Grignard reagent and a suitable carbonyl-containing compound? Write chemical reactions for these preparations using any starting materials you wish; indicate stoichiometry where important.

13. What molecular feature or features allow carbon dioxide to function as an electrophile?

15. Why is it necessary to acidify the mixture obtained after the reaction of phenyl- magnesium bromide with carbon dioxide?

19. The yield of benzoic acid obtained when only enough acid is added to the aqueous solution of sodium benzoate to bring the pH to 7 is lower than that obtained if the pH is brought below 5. Explain.

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The solution discusses organometallic and grignard reactions.

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Organometallic Chemistry and Reaction Types

Hi, I need some help with these questions:
5. In the experiment, ligroin may be used as a solvent for the separation of
the product from biphenyl.
a. What is ligroin?
b. Can you suggest an alternative solvent that might be used in
this step?

9. Consider the same reaction as in the previous question (#8) except that in
this case it is carried out with ethyl benzoate. What product would be i
expected in this case?

10. Grignard reagents may be used to prepare other organometallic reagents,
for example, ethylmagnesium bromide reacts with cadmium chloride to
yield diethylcadmium.
2 CH3CH2MgCI + CdCI2 (CH3CH2)2Cd + 2 MgCI2
Indicate the product of the following reactions and name the
organometallic product.
4 CH3MgCI + SiCI4 2 C6HsMgCI + HgCI2 11. para-Nitrobenzaldehyde reacts at a faster rate than benzaldehyde in the
Perkin reaction while p-N,N-dimethylaminobenzaldehyde is much less
reactive toward the same nucleophile. Explain.

18. It is likely that the amount of Grignard reagent your analysis indicates was
formed is greater than the amount of Grignard reagent actually present
just before you added water. Explain.

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