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Topic: Mechanism request  (Read 4985 times)

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Offline ShinyDiamond

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Mechanism request
« on: April 08, 2016, 11:32:17 AM »
Can somebody help me: the questions are in the picture attached below.
« Last Edit: April 08, 2016, 11:48:16 AM by sjb »
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Offline sjb

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Re: Help
« Reply #1 on: April 08, 2016, 11:47:55 AM »
O=C(O)c1ccccc1C(O)C2CCCCC2 to O=C2OC(C1CCCCC1)c3ccccc23

Do you recognise the reaction?
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Offline ShinyDiamond

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Re: Mechanism request
« Reply #2 on: April 08, 2016, 12:06:06 PM »
Hey sjb, whats that have to do with the mechanism for the reactions?
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Offline Guitarmaniac86

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Re: Mechanism request
« Reply #3 on: April 08, 2016, 12:26:44 PM »
Quote from: ShinyDiamond on April 08, 2016, 12:06:06 PM
Hey sjb, whats that have to do with the mechanism for the reactions?

What type of reaction occurs when an alcohol and a carboxylic acid react together? This reaction can be both acid and base catalysed. The product formed is what?
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Offline ShinyDiamond

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Re: Mechanism request
« Reply #4 on: April 08, 2016, 01:11:33 PM »
Quote from: Guitarmaniac86 on April 08, 2016, 12:26:44 PM
Quote from: ShinyDiamond on April 08, 2016, 12:06:06 PM
Hey sjb, whats that have to do with the mechanism for the reactions?

What type of reaction occurs when an alcohol and a carboxylic acid react together? This reaction can be both acid and base catalysed. The product formed is what?

The reaction will go under certain mechanisms to give us the shown product , now to reach the final product we should know all reagents that help us to do the mechanisms actually there are 2 mechanisms
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Offline ShinyDiamond

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Re: Mechanism request
« Reply #5 on: April 08, 2016, 01:20:59 PM »
Keep in mind that they are all benzene rings in both reactant and product
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Offline kriggy

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Re: Mechanism request
« Reply #6 on: April 08, 2016, 01:31:03 PM »
Quote from: Guitarmaniac86 on April 08, 2016, 12:26:44 PM
Quote from: ShinyDiamond on April 08, 2016, 12:06:06 PM
Hey sjb, whats that have to do with the mechanism for the reactions?

What type of reaction occurs when an alcohol and a carboxylic acid react together? This reaction can be both acid and base catalysed. The product formed is what?

Yeah I dont realy think the reaction can be base catalyzed.. What happens when you mix carboxilic acid and base?

@ShinyDiamond: Please keep in mind that you need to show your own attempts to receive help.
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Offline Guitarmaniac86

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Re: Mechanism request
« Reply #7 on: April 08, 2016, 01:32:48 PM »
Quote from: kriggy on April 08, 2016, 01:31:03 PM
Quote from: Guitarmaniac86 on April 08, 2016, 12:26:44 PM
Quote from: ShinyDiamond on April 08, 2016, 12:06:06 PM
Hey sjb, whats that have to do with the mechanism for the reactions?

What type of reaction occurs when an alcohol and a carboxylic acid react together? This reaction can be both acid and base catalysed. The product formed is what?

Yeah I dont realy think the reaction can be base catalyzed.. What happens when you mix carboxilic acid and base?

@ShinyDiamond: Please keep in mind that you need to show your own attempts to receive help.

My mistake on the base, I was thinking about the product which can be hydrolysed by base.
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Offline ShinyDiamond

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Re: Mechanism request
« Reply #8 on: April 08, 2016, 03:56:17 PM »
What happens when you mix carboxilic acid and base?
Answer: it will converts to carboxylate.

I will attach a modified reaction and please can somebody help me. English is not my mother language
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Offline Babcock_Hall

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Re: Mechanism request
« Reply #9 on: April 08, 2016, 04:06:50 PM »
ShinyDiamond,

You must show us your attempt or your thoughts before we can help you.  My interpretation of the "two ways" of the first part of the question is that they will give two distinct predictions about what will happen in the second part of the question, the part that involves an isotope.  In other words the isotope experiment will allow us to discriminate between the two ways.
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Offline ShinyDiamond

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Re: Mechanism request
« Reply #10 on: April 08, 2016, 04:44:49 PM »
Everybody please excuse me for not trying much, however this one mechanism that I tried. What do you think?
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Offline Babcock_Hall

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Re: Mechanism request
« Reply #11 on: April 08, 2016, 06:29:53 PM »
I would avoid intermediates which do not have a full Lewis octet.  Try protonating the carboxylic acid group, for example.
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Offline sjb

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Re: Mechanism request
« Reply #12 on: April 09, 2016, 06:04:02 AM »
Quote from: ShinyDiamond on April 08, 2016, 01:20:59 PM
Keep in mind that they are all benzene rings in both reactant and product

oops. Was concentrating on getting the SMILES right for the product and missed this. Still, the principle is the same.
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