Comments on: Reagent Friday: Sodium (Na) https://www.masterorganicchemistry.com/2011/10/07/reagent-friday-sodium-na/ Wed, 29 Jan 2020 20:47:30 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: James Ashenhurst https://www.masterorganicchemistry.com/2011/10/07/reagent-friday-sodium-na/#comment-560508 Tue, 13 Aug 2019 20:58:49 +0000 https://www.masterorganicchemistry.com/?p=2410#comment-560508 In reply to Neeraj.

Yes, it’s possible to do a Birch reduction of toluene using sodium metal.

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By: Neeraj https://www.masterorganicchemistry.com/2011/10/07/reagent-friday-sodium-na/#comment-560260 Sat, 10 Aug 2019 03:57:11 +0000 https://www.masterorganicchemistry.com/?p=2410#comment-560260 Hii.. Will sodium metal react with Toluene..?

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By: James Ashenhurst https://www.masterorganicchemistry.com/2011/10/07/reagent-friday-sodium-na/#comment-555508 Tue, 21 May 2019 04:03:23 +0000 https://www.masterorganicchemistry.com/?p=2410#comment-555508 In reply to Om.

No, because only the OH bond is broken giving the alkoxide. The C-O bond is unaffected.

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By: Om https://www.masterorganicchemistry.com/2011/10/07/reagent-friday-sodium-na/#comment-555453 Sun, 19 May 2019 10:31:19 +0000 https://www.masterorganicchemistry.com/?p=2410#comment-555453 What happens if I react sodium with chiral carboned alcohol does it’s chirality or configuration retained

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By: James Ashenhurst https://www.masterorganicchemistry.com/2011/10/07/reagent-friday-sodium-na/#comment-549292 Fri, 08 Mar 2019 19:10:28 +0000 https://www.masterorganicchemistry.com/?p=2410#comment-549292 In reply to Emanuel Greyson.

Well, that is an excellent question. The prevailing opinion is that the blue color of sodium dissolved in liquid ammonia is due to solvated electrons, and it is the electrons that perform the reduction. One could (and it is has been done) alternatively use electrochemical means to perform these reactions. See: http://openflask.blogspot.com/2019/02/e-birch.html
In those cases, it appears that reduction is not due to free electrons, but occurs at the surface of the electrode.

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By: James Ashenhurst https://www.masterorganicchemistry.com/2011/10/07/reagent-friday-sodium-na/#comment-549289 Fri, 08 Mar 2019 19:07:47 +0000 https://www.masterorganicchemistry.com/?p=2410#comment-549289 In reply to Shadow_of_death.

Glad to hear it. Thanks!

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By: James Ashenhurst https://www.masterorganicchemistry.com/2011/10/07/reagent-friday-sodium-na/#comment-549288 Fri, 08 Mar 2019 19:07:39 +0000 https://www.masterorganicchemistry.com/?p=2410#comment-549288 In reply to Moriarty.

Best approach if you are looking to reduce off a bromo group is just to employ lithium halogen exchange with n-butyllithium or t-butyllithium depending on whether it’s sp2 or sp3. Very clean and fast reaction.

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By: James Ashenhurst https://www.masterorganicchemistry.com/2011/10/07/reagent-friday-sodium-na/#comment-549287 Fri, 08 Mar 2019 19:06:21 +0000 https://www.masterorganicchemistry.com/?p=2410#comment-549287 In reply to vasant phadke.

A very low temperature is required because the boiling point of ammonia is –33 °C. Ammonia is a gas at room temperature, which makes it unsuitable.
In order to obtain liquid ammonia, ammonia gas is passed through a flask attached to a coldfinger apparatus (usually dry ice / acetone).

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By: James Ashenhurst https://www.masterorganicchemistry.com/2011/10/07/reagent-friday-sodium-na/#comment-549285 Fri, 08 Mar 2019 19:03:28 +0000 https://www.masterorganicchemistry.com/?p=2410#comment-549285 In reply to Sneha.

The resulting (sp3) carbanion would be many orders ( >10) of magnitude less stable than the (sp2) carbanion, and sodium doesn’t have the reduction potential to make that possible. One exception is alkenes adjacent to an electron withdrawing group (such as an ester) which can stabilize the negative charge. It turns out the pKa of the resulting anion is a pretty good guide to what species can be reduced.

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By: James Ashenhurst https://www.masterorganicchemistry.com/2011/10/07/reagent-friday-sodium-na/#comment-549282 Fri, 08 Mar 2019 19:02:20 +0000 https://www.masterorganicchemistry.com/?p=2410#comment-549282 In reply to Jacob Joshy.

No, it’s trans-2-butene.

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