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Topic: NaBH4 and H2SO4 is supposed to reduce the aldehyde on the left of this molecule?  (Read 10213 times)

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Offline discodermolide

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Re: NaBH4 and H2SO4 is supposed to reduce the aldehyde on the left of this molecule?
« Reply #15 on: March 14, 2013, 12:06:34 AM »
Again ester formation.
O=C1CCCCO1
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Offline theanonymous

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Re: NaBH4 and H2SO4 is supposed to reduce the aldehyde on the left of this molecule?
« Reply #16 on: March 14, 2013, 12:12:49 AM »
Quote from: discodermolide on March 14, 2013, 12:06:34 AM
Again ester formation.
O=C1CCCCO1

:O

I was close!

Ok ok ok...this is the very very last one! I promise!



I know this forms when but-1-ene reacts with HBr



I'm not sure about NaCN
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Offline discodermolide

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Re: NaBH4 and H2SO4 is supposed to reduce the aldehyde on the left of this molecule?
« Reply #17 on: March 14, 2013, 12:17:39 AM »
Well assuming your first product is correct NaCN will displace the bromine to give
CCCCC#N

What happens when you heat nitriles with acid?
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Offline theanonymous

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Re: NaBH4 and H2SO4 is supposed to reduce the aldehyde on the left of this molecule?
« Reply #18 on: March 14, 2013, 12:25:44 AM »
Quote from: discodermolide on March 14, 2013, 12:17:39 AM
Well assuming your first product is correct NaCN will displace the bromine to give
CCCCC#N

What happens when you heat nitriles with acid?

An acid such as HCl?
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Offline discodermolide

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Re: NaBH4 and H2SO4 is supposed to reduce the aldehyde on the left of this molecule?
« Reply #19 on: March 14, 2013, 12:27:08 AM »
Yes, for example conc. aqueous HCl. What happens to the nitrile?
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Offline theanonymous

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Re: NaBH4 and H2SO4 is supposed to reduce the aldehyde on the left of this molecule?
« Reply #20 on: March 14, 2013, 12:28:36 AM »
Quote from: discodermolide on March 14, 2013, 12:27:08 AM
Yes, for example conc. aqueous HCl. What happens to the nitrile?

It gets attacked and replaced by Cl-?
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Offline discodermolide

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Re: NaBH4 and H2SO4 is supposed to reduce the aldehyde on the left of this molecule?
« Reply #21 on: March 14, 2013, 12:30:15 AM »
Nope, it hydrolyses to the acid.
CCCCC(O)=O

which is your final product.
Note the chain elongation by 1 carbon!
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Offline theanonymous

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Re: NaBH4 and H2SO4 is supposed to reduce the aldehyde on the left of this molecule?
« Reply #22 on: March 14, 2013, 12:32:54 AM »
Quote from: discodermolide on March 14, 2013, 12:30:15 AM
Nope, it hydrolyses to the acid.
CCCCC(O)=O

which is your final product.
Note the chain elongation by 1 carbon!

That was my next guess! :D

What about the last part of the question
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Offline discodermolide

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Re: NaBH4 and H2SO4 is supposed to reduce the aldehyde on the left of this molecule?
« Reply #23 on: March 14, 2013, 12:39:50 AM »
Well this is a http://en.wikipedia.org/wiki/Hell–Volhard–Zelinsky_halogenation,
which gives initially, at least with bromine this compound
CCCC(Br)C(Br)=O

After an aqueous work-up you will get this as the final product.
CCCC(Br)C(O)=O
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Offline theanonymous

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Re: NaBH4 and H2SO4 is supposed to reduce the aldehyde on the left of this molecule?
« Reply #24 on: March 14, 2013, 12:41:43 AM »
Quote from: discodermolide on March 14, 2013, 12:39:50 AM
Well this is a http://en.wikipedia.org/wiki/Hell–Volhard–Zelinsky_halogenation,
which gives initially, at least with bromine this compound
CCCC(Br)C(Br)=O

After an aqueous work-up you will get this as the final product.
CCCC(Br)C(O)=O

Thank you SOOOO MUCH!!
You relieved a lot of stress and made my day! :D
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Offline discodermolide

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Re: NaBH4 and H2SO4 is supposed to reduce the aldehyde on the left of this molecule?
« Reply #25 on: March 14, 2013, 12:43:10 AM »
My pleasure. Till the next panic. 8)
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Offline theanonymous

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Re: NaBH4 and H2SO4 is supposed to reduce the aldehyde on the left of this molecule?
« Reply #26 on: March 14, 2013, 12:44:57 AM »
Lol! Yes indeed! But ill show my work better next time like last time :D
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