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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: theanonymous on April 03, 2013, 08:47:33 PM

Title: URGENT: Lactone does NOT form from this intramolecular esterification problem!?
Post by: theanonymous on April 03, 2013, 08:47:33 PM
(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fi697.photobucket.com%2Falbums%2Fvv331%2Femreturned%2FIntamolecularEsterification.png&hash=46401f808328acca27976801f89e6c38776edbb4)

This problem is making my life difficult...
Title: Re: Lactone does NOT form from this intramolecular esterification problem!!??
Post by: theanonymous on April 03, 2013, 08:48:40 PM
This is what I did - these are my notes because my teachers "example" is nothing like this and her "notes" online are awful/difficult to follow.

(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fi697.photobucket.com%2Falbums%2Fvv331%2Femreturned%2FIE2.png&hash=ab6eab202d90dc20efc2ca48a01879fbd7abe452)

(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fi697.photobucket.com%2Falbums%2Fvv331%2Femreturned%2FIE3.png&hash=154aba9c3a90d688a19e5819dbb1e95f33a451b5)

(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fi697.photobucket.com%2Falbums%2Fvv331%2Femreturned%2FIEnew.png&hash=bfc07a8ac1e39023b520f6023b464a1ead8e6f12)

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Title: Re: Lactone does NOT form from this intramolecular esterification problem!!??
Post by: theanonymous on April 03, 2013, 08:49:59 PM
Is that the answer??
Title: Re: URGENT: Lactone does NOT form from this intramolecular esterification problem!?
Post by: theanonymous on April 03, 2013, 11:55:03 PM
 ??? ???
Title: Re: URGENT: Lactone does NOT form from this intramolecular esterification problem!?
Post by: discodermolide on April 04, 2013, 12:32:50 AM
Why should the lactone not form?
I suppose the other thing which could happen is these after reduction and then treatment with sulphuric acid/water it eliminates water to put a C=C in there? But this is less likely.
Title: Re: URGENT: Lactone does NOT form from this intramolecular esterification problem!?
Post by: theanonymous on April 04, 2013, 12:57:18 AM
Quote from: discodermolide on April 04, 2013, 12:32:50 AM
Why should the lactone not form?
I suppose the other thing which could happen is these after reduction and then treatment with sulphuric acid/water it eliminates water to put a C=C in there? But this is less likely.

:(
And I don't even know the answer to this question because it's a practice problem on my professor's slide.
I'm studying ahead for our test next Tuesday, but this problem, in particular has given me a headache...

I have to go back to my dorm cause it's 1 am here!
I'll come back to see if you'll still be here sometime tomorrow morning, before 9:45 AM
Title: Re: URGENT: Lactone does NOT form from this intramolecular esterification problem!?
Post by: Dan on April 04, 2013, 03:13:28 AM
Quote from: theanonymous on April 04, 2013, 12:57:18 AM
I don't even know the answer to this question

If you don't know the answer, what is the basis for your claiming that the lactone does not form in the thread subject?

The answer you posted looks perfectly reasonable to me.
Title: Re: URGENT: Lactone does NOT form from this intramolecular esterification problem!?
Post by: theanonymous on April 04, 2013, 08:04:43 AM
Quote from: Dan on April 04, 2013, 03:13:28 AM
Quote from: theanonymous on April 04, 2013, 12:57:18 AM
I don't even know the answer to this question

If you don't know the answer, what is the basis for your claiming that the lactone does not form in the thread subject?

The answer you posted looks perfectly reasonable to me.

Ohh!!! xD
I just realized that lactone has different types
I thought lactone had only one structure (the third structure below)

(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fupload.wikimedia.org%2Fwikipedia%2Fcommons%2F2%2F26%2FLactone_Types.png&hash=cb72da2c58e6d9036c2bfe93d8b2f69b214e609e)

I didn't know that...
thanks everyone!!