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Topic: QUICK question: What is the structure of N-tert-butyl-N-propylpentanamide?  (Read 7463 times)

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Offline theanonymous

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QUICK question: What is the structure of N-tert-butyl-N-propylpentanamide?
« on: March 14, 2013, 08:01:08 AM »


ALSO,

What should the answer to part b of this question look like. The structure I drew is essentially right I think but it's the Deuteriums that's giving me trouble.

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Offline Dan

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Re: QUICK question: What is the structure of N-tert-butyl-N-propylpentanamide?
« Reply #1 on: March 14, 2013, 08:05:58 AM »
1. Step 1: Draw pentanamide. Step 2: Add N-tert-butyl substituent. Step 3: Add N-propyl substituent.

2. Google the mechanism of LiAlH4 reduction (or better, look it up in a textbook). Draw the corresponding mechanism with LiAlD4. There is no way you could have logically come up with the structure you put down if you drew out the mechanism.
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Offline discodermolide

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Re: QUICK question: What is the structure of N-tert-butyl-N-propylpentanamide?
« Reply #2 on: March 14, 2013, 08:08:46 AM »
The structure is
O=C(CCCC)N(CCC)C(C)(C)C


The reduction should give you
-CD2-OD
« Last Edit: March 14, 2013, 08:26:28 AM by discodermolide »
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Offline theanonymous

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Re: QUICK question: What is the structure of N-tert-butyl-N-propylpentanamide?
« Reply #3 on: March 14, 2013, 08:16:16 AM »
Thanks both of you!!
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Offline mamid

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Re: QUICK question: What is the structure of N-tert-butyl-N-propylpentanamide?
« Reply #4 on: March 14, 2013, 08:23:06 AM »
discodermolide, the propyl is also attached to N!!!
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Offline discodermolide

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Re: QUICK question: What is the structure of N-tert-butyl-N-propylpentanamide?
« Reply #5 on: March 14, 2013, 08:27:05 AM »
Quote from: mamid on March 14, 2013, 08:23:06 AM
discodermolide, the propyl is also attached to N!!!

Thank you for noticing my error, it's been corrected.
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Offline theanonymous

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Re: QUICK question: What is the structure of N-tert-butyl-N-propylpentanamide?
« Reply #6 on: March 14, 2013, 08:29:14 AM »
Hmm...



I did draw out the mechanism many times but i don't know what's going on...
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Offline discodermolide

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Re: QUICK question: What is the structure of N-tert-butyl-N-propylpentanamide?
« Reply #7 on: March 14, 2013, 08:37:16 AM »
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Offline theanonymous

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Re: QUICK question: What is the structure of N-tert-butyl-N-propylpentanamide?
« Reply #8 on: March 14, 2013, 08:47:01 AM »
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Offline discodermolide

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Re: QUICK question: What is the structure of N-tert-butyl-N-propylpentanamide?
« Reply #9 on: March 14, 2013, 08:51:05 AM »
The mechanism of the reduction is in there.
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Offline theanonymous

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Re: QUICK question: What is the structure of N-tert-butyl-N-propylpentanamide?
« Reply #10 on: March 14, 2013, 09:02:48 AM »
Quote from: discodermolide on March 14, 2013, 08:51:05 AM
The mechanism of the reduction is in there.

Hmm...
I think im missing something...
i'll keep checking
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Offline discodermolide

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Re: QUICK question: What is the structure of N-tert-butyl-N-propylpentanamide?
« Reply #11 on: March 14, 2013, 09:10:23 AM »
have a look here under complex metal reductions.
http://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/crbacid2.htm
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Offline theanonymous

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Re: QUICK question: What is the structure of N-tert-butyl-N-propylpentanamide?
« Reply #12 on: March 14, 2013, 09:17:03 AM »
Quote from: discodermolide on March 14, 2013, 09:10:23 AM
have a look here under complex metal reductions.
http://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/crbacid2.htm

Ohhh!!!

There's supposed to be an OH at the bottom right!
Thanks!!
I got the answer :D
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Offline discodermolide

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Re: QUICK question: What is the structure of N-tert-butyl-N-propylpentanamide?
« Reply #13 on: March 14, 2013, 09:21:40 AM »
Want to share it with us for others who might follow in your path?
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Offline theanonymous

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Re: QUICK question: What is the structure of N-tert-butyl-N-propylpentanamide?
« Reply #14 on: March 14, 2013, 11:42:58 AM »
Quote from: discodermolide on March 14, 2013, 09:21:40 AM
Want to share it with us for others who might follow in your path?



That's the answer! :D
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