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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: shalikadm on June 22, 2012, 03:04:42 PM

Title: Hydrolysis of Organic compounds
Post by: shalikadm on June 22, 2012, 03:04:42 PM
The following compounds can be hydrolyzed using strong acids..Can we use bases for that ?
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And the following compounds can be hydrolyzed using bases.Can we use acids for that?
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Title: Re: Hydrolysis of Organic compounds
Post by: discodermolide on June 22, 2012, 03:17:30 PM
The following compounds can be hydrolyzed using strong acids..Can we use bases for that ?
(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fs7.postimage.org%2Faep6ikkgb%2Fimage.png&hash=a75eea7b352c3916b19444f6a6f5167f)
And the following compounds can be hydrolyzed using bases.Can we use acids for that?
(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fs15.postimage.org%2Fug2r0ja2j%2FUntitled.png&hash=22aff832a9e52933da8e9c7984c09590)

Have you any ideas to these questions?
Title: Re: Hydrolysis of Organic compounds
Post by: shalikadm on June 22, 2012, 03:20:42 PM
The following compounds can be hydrolyzed using strong acids..Can we use bases for that ?
(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fs7.postimage.org%2Faep6ikkgb%2Fimage.png&hash=a75eea7b352c3916b19444f6a6f5167f)
And the following compounds can be hydrolyzed using bases.Can we use acids for that?
(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fs15.postimage.org%2Fug2r0ja2j%2FUntitled.png&hash=22aff832a9e52933da8e9c7984c09590)

Have you any ideas to these questions?


No idea about it..Our book only give the above things...I'm wondering why can't we use acid or base also ?
Title: Re: Hydrolysis of Organic compounds
Post by: discodermolide on June 22, 2012, 03:37:39 PM
You must have some thoughts. Showing an attempt is part of thr Forum rules.
Title: Re: Hydrolysis of Organic compounds
Post by: shalikadm on June 22, 2012, 03:42:08 PM
You must have some thoughts. Showing an attempt is part of thr Forum rules.

As I think..
acids and bases are mere catalysts..So we can use either acid or base in the process maybe with heat.. :)
Title: Re: Hydrolysis of Organic compounds
Post by: discodermolide on June 22, 2012, 03:51:43 PM
You must have some thoughts. Showing an attempt is part of thr Forum rules.

As I think..
acids and bases are mere catalysts..So we can use either acid or base in the process maybe with heat.. :)

For the first two bases ,e.g. NaOH will exchange and you will get the Mg(OH)Br and the corresponding alcohol and acid  
Respectively .
The amide will hydrolyze under both sets of conditions with heating.
The nitro aniline will not react.
Title: Re: Hydrolysis of Organic compounds
Post by: shalikadm on June 22, 2012, 03:58:23 PM
You must have some thoughts. Showing an attempt is part of thr Forum rules.

As I think..
acids and bases are mere catalysts..So we can use either acid or base in the process maybe with heat.. :)


The nitro aniline will not react.

What is the reason?..anyway bromo aniline reacts when there is acid..
Title: Re: Hydrolysis of Organic compounds
Post by: discodermolide on June 22, 2012, 04:39:15 PM
You must have some thoughts. Showing an attempt is part of thr Forum rules.

As I think..
acids and bases are mere catalysts..So we can use either acid or base in the process maybe with heat.. :)


The nitro aniline will not react.

What is the reason?..anyway bromo aniline reacts when there is acid..

What does bromo aniline give?
Title: Re: Hydrolysis of Organic compounds
Post by: shalikadm on June 23, 2012, 01:39:27 AM
Oooops..Sorry ...I have put something wrong...It's not nitro aniline...It must be an amide..
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I know..
Aniline and its derivatives acts as bases..Because the both bromo and nitro derivatives have lone electron pairs to act like bases..But there's no hydrolysis for aniline and its derivatives...
Sorry for that  ;)
Title: Re: Hydrolysis of Organic compounds
Post by: discodermolide on June 23, 2012, 01:47:49 AM
Oooops..Sorry ...I have put something wrong...It's not nitro aniline...It must be an amide..
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I know..
Aniline and its derivatives acts as bases..Because the both bromo and nitro derivatives have lone electron pairs to act like bases..But there's no hydrolysis for aniline and its derivatives...
Sorry for that  ;)

No problem.
That anilide will hydroyse with acid or base with heating to give the amine.
Title: Re: Hydrolysis of Organic compounds
Post by: shalikadm on June 26, 2012, 12:31:00 AM
And then what about the alkyl halide?(ethylbromide..)
I found that it can be hydrolyzed with dil.NaoHaq.If not happens an elimination.
Can we use an acid for the hydrolysis...?
Benzyl bromide seems to act with water even without catalysts..Doesn't the ethylbromide have that capability ?
Title: Re: Hydrolysis of Organic compounds
Post by: discodermolide on June 26, 2012, 12:37:42 AM
And then what about the alkyl halide?(ethylbromide..)
I found that it can be hydrolyzed with dil.NaoHaq.If not happens an elimination.
Can we use an acid for the hydrolysis...?
Benzyl bromide seems to act with water even without catalysts..Doesn't the ethylbromide have that capability ?

Firstly ethyl bromide is a gas at RT.
Acid cannot be used for it's hydrolysis.
The reactivity of benzyl bromide is orders of magnitude greater than that of ethyl bromide. In spite of that its reactivity with water is still relatively slow under normal conditions.
Title: Re: Hydrolysis of Organic compounds
Post by: shalikadm on June 26, 2012, 07:57:38 AM
1.sodium ethoxide hydrolyzes in this way..
C2H5ONa + H2O → C2H5OH + NaOH
Does sodium phenoxide hydrolyze in that way ?
Is it in equilibrium as NaOH reacts with phenol ?
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2.The following compounds give tertiary alcohols when hydrolyzed.What will be the other compound in each reaction ?.. I guess something like AlH3LiOH and BH3NaOH..am I correct ?
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Title: Re: Hydrolysis of Organic compounds
Post by: discodermolide on June 26, 2012, 08:02:59 AM
1.sodium ethoxide hydrolyzes in this way..
C2H5ONa + H2O → C2H5OH + NaOH
Does sodium phenoxide hydrolyze in that way ?
Is it in equilibrium as NaOH reacts with phenol ?
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2.The following compounds give tertiary alcohols when hydrolyzed.What will be the other compound in each reaction ?.. I guess something like AlH3LiOH and BH3NaOH..am I correct ?
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The phenoxide hydrolysis looks ok.
The second set of reactions look strange to me, in terms of structure, LAH is already an ionic compound as is sodium borohydride, so I guess complete hydrolysis would give aluminum oxide and lithium hydroxide and boric acid and sodium hydroxide.
Title: Re: Hydrolysis of Organic compounds
Post by: shalikadm on June 26, 2012, 09:46:41 AM
Here I made a short note of hydrolysis..Please check it for me..thanks !
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Title: Re: Hydrolysis of Organic compounds
Post by: discodermolide on June 26, 2012, 09:52:52 AM
What exactly do you want to know?
I noticed the LAH and NaBH4 reactions are missing a product!
Otherwise there is really a lot to look at here.
Title: Re: Hydrolysis of Organic compounds
Post by: shalikadm on June 26, 2012, 09:56:19 AM
I noticed the LAH and NaBH4 reactions are missing a product!
ya..they are not relevant to our syllabus..
What exactly do you want to know?
Otherwise there is really a lot to look at here.
I wanted to check whether I've done it correctly... :)
Title: Re: Hydrolysis of Organic compounds
Post by: discodermolide on June 26, 2012, 11:29:54 AM
I noticed the LAH and NaBH4 reactions are missing a product!
ya..they are not relevant to our syllabus..
What exactly do you want to know?
Otherwise there is really a lot to look at here.
I wanted to check whether I've done it correctly... :)

It looks OK, except I would not call the diazonium salt reaction a hydrolysis, this is the Sandmeyer reaction.
And the other products produced in a reaction are always relevant and you should know what they are, syllabus or not.

Title: Re: Hydrolysis of Organic compounds
Post by: buRnINGbeND on June 26, 2012, 04:32:46 PM
you need to step back and think about what's going on with each molecule you've posted.  if you try to hydrolyze a basic organic compound with a strong base, do you think it's going to do anything?  if you try to hydrolyze an acidic organic compound with a strong acid, do you think it's going to do anything?

i.e. if you throw in a bunch of NaOH crystals in a solution of phenyllithium, is anything going to actually happen in your flask?
if you throw in a bunch of TfOH in a solution of phenyllithium, is anything going to happen in your flask?