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Topic: Reduction of carboxylic acids to aldehydes with CaH2  (Read 40353 times)

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Offline yufgyfyu

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Re: Reduction of carboxylic acids to aldehydes with CaH2
« Reply #15 on: May 17, 2011, 02:23:53 PM »
 Does not CaH2 reduce H2O to H2.
CaH2 is a base not a reducing agent.  much like you cant reduce carbonyls with NaH.  The s-orbitals of the hydride are non-directional (by definition) and are, therefore, terrible nucleophiles.  Reflux with LAH or use borane

Offline discodermolide

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Re: Reduction of carboxylic acids to aldehydes with CaH2
« Reply #16 on: May 17, 2011, 02:54:44 PM »
In any case, How can CaH2 react to produce H2 and the calcium salt of the acid?

CaH2 + 2H2O ------> Ca(OH)2 + 2H2

It does the same with carboxylic acids to give the Ca salt of the acid
, Ca2+(RCOO-)2
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Offline yufgyfyu

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Re: Reduction of carboxylic acids to aldehydes with CaH2
« Reply #17 on: May 17, 2011, 03:07:55 PM »
 I wrote


      2 RCOOH + CaH2 ----> 2 RCOH + Ca(OH)2


   Where do you see H2O?

Offline yufgyfyu

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Re: Reduction of carboxylic acids to aldehydes with CaH2
« Reply #18 on: May 17, 2011, 03:23:17 PM »
 Okay then write the formula for the reaction of acetic acid and calcium hydride and show me how H2 is produced.
Quote from: discodermolide don't include water.link=topic=48774.msg183291#msg183291 date=1305658484
In any case, How can CaH2 react to produce H2 and the calcium salt of the acid?

CaH2 + 2H2O ------> Ca(OH)2 + 2H2

It does the same with carboxylic acids to give the Ca salt of the acid
, Ca2+(RCOO-)2

Offline discodermolide

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Re: Reduction of carboxylic acids to aldehydes with CaH2
« Reply #19 on: May 17, 2011, 03:34:18 PM »
Okay then write the formula for the reaction of acetic acid and calcium hydride and show me how H2 is produced.
Quote from: discodermolide don't include water.link=topic=48774.msg183291#msg183291 date=1305658484
In any case, How can CaH2 react to produce H2 and the calcium salt of the acid?

CaH2 + 2H2O ------> Ca(OH)2 + 2H2

It does the same with carboxylic acids to give the Ca salt of the acid
, Ca2+(RCOO-)2



2CH3COOH + CaH2 -----------> (CH3COO-)2Ca2+ + 2H2

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Offline discodermolide

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Re: Reduction of carboxylic acids to aldehydes with CaH2
« Reply #20 on: May 17, 2011, 03:36:20 PM »
I wrote


      2 RCOOH + CaH2 ----> 2 RCOH + Ca(OH)2


   Where do you see H2O?

Nowhere, but this reaction is a reduction , as written, and CaH2 is not a reducing agent
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Offline yufgyfyu

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Re: Reduction of carboxylic acids to aldehydes with CaH2
« Reply #21 on: May 17, 2011, 03:41:35 PM »
 Doesn't CaH2 reduce H2O to H2? Making it the reducer?

Offline discodermolide

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Re: Reduction of carboxylic acids to aldehydes with CaH2
« Reply #22 on: May 17, 2011, 03:51:11 PM »
Doesn't CaH2 reduce H2O to H2? Making it the reducer?

This is not a redox reaction but an acid/base system
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Offline yufgyfyu

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Re: Reduction of carboxylic acids to aldehydes with CaH2
« Reply #23 on: May 17, 2011, 04:01:20 PM »
You may have won this round, but you've made a powerful enemy.

Offline discodermolide

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Re: Reduction of carboxylic acids to aldehydes with CaH2
« Reply #24 on: May 17, 2011, 04:06:29 PM »
You may have won this round, but you've made a powerful enemy.

Enemy, I hope not:)).
I enjoy discussing chemistry even if I am right or wrong.
See you back here sometime
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Offline Honclbrif

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Re: Reduction of carboxylic acids to aldehydes with CaH2
« Reply #25 on: May 17, 2011, 04:12:24 PM »
Doesn't CaH2 reduce H2O to H2? Making it the reducer?

This is not a redox reaction but an acid/base system

I think acid-base and redox both describe this reaction. I think of it as a comproportionation reaction where H- and H+ form H2 with H in the zero oxidation state. Hydride is the reductant, and H+ is the oxidant.

If you go by the Usanovich definition of acid-base behavior, any redox reaction is and acid-base reaction.
Individual results may vary

Offline yufgyfyu

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Re: Reduction of carboxylic acids to aldehydes with CaH2
« Reply #26 on: May 17, 2011, 04:17:53 PM »
 Yeah I was just joking about the enemy thing.

Offline nox

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Re: Reduction of carboxylic acids to aldehydes with CaH2
« Reply #27 on: May 18, 2011, 12:56:58 PM »
Wow first you necro a 7 year old thread then this?? Unbelievable.

Offline discodermolide

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Re: Reduction of carboxylic acids to aldehydes with CaH2
« Reply #28 on: May 18, 2011, 01:19:47 PM »
Wow first you necro a 7 year old thread then this?? Unbelievable.
Perhaps you could explain your remarks?
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Offline Dan

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Re: Reduction of carboxylic acids to aldehydes with CaH2
« Reply #29 on: May 18, 2011, 02:38:41 PM »
I think nox is pointing out that that BenFrank1 has so far managed to resurrect a dead 7 month old thread and post mostly nonsense in this one with a rather heavy dose of misplaced arrogance. Not the most auspicious start to chemicalforums life...

Hey azmanam, do you have any of that popcorn left?
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