Chloroform Reactions with Metals & Alkoxides

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In summary, chloroform has been reported to react violently with a variety of metals including Al, Na, Li, Mg, K, Fe, and Zn, as well as with sodium methoxide (CH3ONa). It is known to form compounds such as CCl3Na with the release of H2, or CHCl2Na+NaCl. There is also concern about its reaction with alkoxides, and whether it mainly reacts with alkali metal methoxides or a wider range of alkoxides. This raises questions about its use as an NMR solvent for alkoxides. Unfortunately, the Gmelin Handbook of Inorganic Chemistry, a valuable resource for answering these questions, has been removed from the
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osskall
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Chloroform is said to react violently with both metals (Al, Na, Li, Mg, K, Fe, Zn) and e.g. sodium methoxide (CH3ONa). Does anyone know more about this? What happens?
Formation of e.g. CCl3Na with release of H2? Or CHCl2Na+NaCl?
And how about reaction with alkoxides?

Does chloroform react with many of the alkoxides or mainly with alkali metal methoxides? Otherwise, it doesn't seem as a smart choice for NMR solvent if one wants to do NMR on alkoxides...

Thank you for your answers.
 
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Help me!

:grumpy: :grumpy: :grumpy: :grumpy: :grumpy:

Aaaaargh! The :devil: :devil: :devil: at the library have removed the Gmelin Handbook of Inorganic Chemistry from the basement. I just faced lots of empty shelves. :confused: Ok they got rid of CAS, because that can be accessed with SciFinder, but Gmelin...?? :cry:
When I asked someone just before closing time where it is now she almost couldn't answer my question, it was just some "Oh, I guess it is at some depository now". It wouldn't surprise me if they threw away everything. They could as well have, I mean if one cannot access the books just for browsing... Gmelin is not something from which you order page xx to page yy. Those who made this decision (as so often with decision-makers) apparently have no clue about the things they decide about (and the consequences the decisions get...)

Now I really need an answer from you guys (chem_tr?) as to what happens when chloroform reacts with metals or metal alkoxides and why, since I'm not even able to consult Gmelin.
 
  • #3


Chloroform (CHCl3) is a highly reactive compound and can undergo various reactions with metals and alkoxides. When reacting with metals, such as Al, Na, Li, Mg, K, Fe, and Zn, chloroform can form metal chlorides and release hydrogen gas. For example, when reacting with sodium (Na), chloroform can form sodium chloride (NaCl) and release hydrogen gas (H2). This reaction is highly exothermic and can be considered violent.

With alkoxides, chloroform can undergo a similar reaction to form alkyl chlorides and release hydrogen gas. For example, when reacting with sodium methoxide (CH3ONa), chloroform can form methyl chloride (CH3Cl) and release hydrogen gas (H2). This reaction can also be considered violent.

The exact products formed in these reactions will depend on the specific metal or alkoxide used, as well as the reaction conditions. In some cases, the reaction may also result in the formation of by-products, such as CCl3Na or CHCl2Na+NaCl.

It is important to note that chloroform is not a suitable solvent for NMR studies involving alkoxides, as it can react with them and produce unwanted by-products. It is recommended to use alternative solvents, such as deuterated solvents, for NMR studies involving alkoxides.
 

1. What is the purpose of using chloroform in reactions with metals and alkoxides?

Chloroform is often used as a solvent in these reactions, as it can dissolve both metals and alkoxides. It also acts as a nucleophilic solvent, meaning it can donate electrons to the reaction and help stabilize intermediates.

2. What types of reactions can be performed with chloroform and metals/alkoxides?

Chloroform can be used in a variety of reactions, including the Grignard reaction and the Darzens reaction. These reactions typically involve the formation of carbon-carbon bonds, and chloroform can act as a reactant or solvent in these processes.

3. How do chloroform reactions with metals and alkoxides differ from reactions with other solvents?

Chloroform is a highly polar solvent, which can affect the rate and selectivity of the reaction. It can also form complexes with metal ions, which can alter the reactivity of the metal in the reaction. Additionally, chloroform can undergo hydrolysis under certain conditions, which can lead to the formation of byproducts.

4. What safety precautions should be taken when working with chloroform in these reactions?

Chloroform is a hazardous chemical and should be handled with care. It is important to work in a well-ventilated area and wear appropriate personal protective equipment, such as gloves and a lab coat. It is also important to properly dispose of any waste products and follow proper storage procedures for chloroform.

5. Are there any limitations to using chloroform in reactions with metals and alkoxides?

Chloroform may not be suitable for all reactions involving metals and alkoxides. It is not compatible with certain functional groups, such as strong acids and bases, and may not be the most effective solvent for certain reactions. Additionally, the use of chloroform may result in the formation of unwanted byproducts, which can affect the yield of the reaction.

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