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Offline orgo814

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organic reactions
« on: June 12, 2012, 11:25:43 PM »
What is the equation for these two acid-base reactions when the following compounds or solutions are mixed? If no appreciable acid-base reaction would occur, you should indicate this.  I could use a little guidance in these.

a) NaH is added to CH3OH.
- For this one would the electrons transfer from the oxygen atom to the H on NaH making CH3OH2 and Na+?

b) NaNH2 is added to CH3CH2OH
- For this one, would the electrons transfer from the oxygen atom to a hydrogen atom on NaNH2 yielding ChCH2OH2 and NaNH?

c) Gaseous NH3 is added to ethyllithium in hexane
- Not sure about this one... the whole "ethyllithium in hexane" is throwing me off

d) NH4Cl is added to sodium amine in liquid ammonia
- Same thing... not sure, the whole "sodium amine in liquid ammonia" is throwing me off. Do I need to do sodium amine + ammonia(l) first and use that product to react with NH4Cl?

e) (CH3)3CONa is added to H2O
Would the electrons flow from the oxygen atom on H2O to the oxygen on (CH3)3CONa? Yielding OH- and (CH3)3COHNa?

f) NaOH is added to (CH3)3COH
Would the electrons flow from oxygen on NaOH to (CH3)3COH? Yielding (CH3)3COH2 and NaO?


Offline Schrödinger

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Re: organic reactions
« Reply #1 on: June 13, 2012, 12:33:04 AM »
a) b) and e) Your theories of electron transfer seem to be at fault. Plus, you also need to take care of charges on the species.

c) Organometallic, just like grignard reagent. Try separating the species into a Li+ cation and the C2H5-anion. This should help

d) Its sodium amide actually. NaNH2. Hint : NaNH2 is a strong base.

f) Once again, the electron transfer problem. What is the property of that peculiar Hydrogen on the tert-butyl alcohol?  Is it acidic or basic?
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Offline discodermolide

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Re: organic reactions
« Reply #2 on: June 13, 2012, 12:33:37 AM »
What is the equation for these two acid-base reactions when the following compounds or solutions are mixed? If no appreciable acid-base reaction would occur, you should indicate this.  I could use a little guidance in these.

a) NaH is added to CH3OH.
- For this one would the electrons transfer from the oxygen atom to the H on NaH making CH3OH2 and Na+?

b) NaNH2 is added to CH3CH2OH
- For this one, would the electrons transfer from the oxygen atom to a hydrogen atom on NaNH2 yielding ChCH2OH2 and NaNH?

c) Gaseous NH3 is added to ethyllithium in hexane
- Not sure about this one... the whole "ethyllithium in hexane" is throwing me off

d) NH4Cl is added to sodium amine in liquid ammonia
- Same thing... not sure, the whole "sodium amine in liquid ammonia" is throwing me off. Do I need to do sodium amine + ammonia(l) first and use that product to react with NH4Cl?

e) (CH3)3CONa is added to H2O
Would the electrons flow from the oxygen atom on H2O to the oxygen on (CH3)3CONa? Yielding OH- and (CH3)3COHNa?

f) NaOH is added to (CH3)3COH
Would the electrons flow from oxygen on NaOH to (CH3)3COH? Yielding (CH3)3COH2 and NaO?



a) NaH + CH3OH  :rarrow: CH3O-Na+ + H2
b)NaNH2 + CH3CH2OH  :rarrow: CH3CH2O-Na+ + NH3
c) NH3 + EtLi  :rarrow: LiNH2 + Et i.e. ethane
d) I think it is sodium amide in liquid ammonia, try think about this one again.
e) (CH3)3CONa + H2O  :rarrow: (CH3)3COH + NaOH
f) I don't think anything will happen.

So I have done a part of your homework apart from d) which you should re-think.
You tell me which are acid and base reactions. Think again about the products you suggest, why are yours different from mine?
« Last Edit: June 13, 2012, 01:01:04 AM by discodermolide »
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Offline orgo814

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Re: organic reactions
« Reply #3 on: June 13, 2012, 12:06:09 PM »
Ok so is it basically the cation replacing a proton? At least that's what I'm getting at.

For C, NH3 + Li+ C2H5 --> LiNH2 + C2H6 (benzene). Is this correct?

For D, NH4Cl + NaNH2 -->
Would this reaction not occur?

For F, why would that reaction not happen?
wouldn't it be NaOH + (CH3)3COH --> (CH3)3CONa + H2O?


Offline discodermolide

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Re: organic reactions
« Reply #4 on: June 13, 2012, 12:35:28 PM »
Ok so is it basically the cation replacing a proton? At least that's what I'm getting at.

For C, NH3 + Li+ C2H5 --> LiNH2 + C2H6 (benzene). Is this correct?

For D, NH4Cl + NaNH2 -->
Would this reaction not occur?

For F, why would that reaction not happen?
wouldn't it be NaOH + (CH3)3COH --> (CH3)3CONa + H2O?



For c) where do you get benzene from? Ethyllithium is a solution in hexane. You get what I stated above.
For d) I think nothing will happen, you may get an exchange of ions and get NaCl.
For f) NaOH is not a strong enough base to deprotonate t-Butyl alcohol. But if it does then your answer is ok.

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Offline orgo814

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Re: organic reactions
« Reply #5 on: June 13, 2012, 01:41:45 PM »
Oh, I thought my thing said C6H6 not C2H6, which is why I wrote benzene. My bad.

For D, the only thing I would think *Could* happen would be a double replacement, but that wouldn't really be an acid-base reaction..?

thanks for the help.

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