December 12, 2024, 02:59:27 AM
Forum Rules: Read This Before Posting


« previous next »
Pages: [1] 2   Go Down

Topic: QUICK question: What is the structure of N-tert-butyl-N-propylpentanamide?  (Read 7857 times)

0 Members and 2 Guests are viewing this topic.

Offline theanonymous

  • Full Member
  • ****
  • Posts: 235
  • Mole Snacks: +1/-14
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.

Logged

Offline Dan

  • Retired Staff
  • Sr. Member
  • *
  • Posts: 4716
  • Mole Snacks: +469/-72
  • Gender: Male
  • Organic Chemist
    • My research
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.
Logged
My research: Google Scholar and Researchgate

Offline discodermolide

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +405/-70
  • Gender: Male
    • My research history
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 »
Logged
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Offline theanonymous

  • Full Member
  • ****
  • Posts: 235
  • Mole Snacks: +1/-14
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!!
Logged

Offline mamid

  • Regular Member
  • ***
  • Posts: 30
  • Mole Snacks: +5/-1
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!!!
Logged

Offline discodermolide

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +405/-70
  • Gender: Male
    • My research history
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.
Logged
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Offline theanonymous

  • Full Member
  • ****
  • Posts: 235
  • Mole Snacks: +1/-14
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...
Logged

Offline discodermolide

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +405/-70
  • Gender: Male
    • My research history
Re: QUICK question: What is the structure of N-tert-butyl-N-propylpentanamide?
« Reply #7 on: March 14, 2013, 08:37:16 AM »
Logged
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Offline theanonymous

  • Full Member
  • ****
  • Posts: 235
  • Mole Snacks: +1/-14
Re: QUICK question: What is the structure of N-tert-butyl-N-propylpentanamide?
« Reply #8 on: March 14, 2013, 08:47:01 AM »
Logged

Offline discodermolide

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +405/-70
  • Gender: Male
    • My research history
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.
Logged
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Offline theanonymous

  • Full Member
  • ****
  • Posts: 235
  • Mole Snacks: +1/-14
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
Logged

Offline discodermolide

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +405/-70
  • Gender: Male
    • My research history
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
Logged
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Offline theanonymous

  • Full Member
  • ****
  • Posts: 235
  • Mole Snacks: +1/-14
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
Logged

Offline discodermolide

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +405/-70
  • Gender: Male
    • My research history
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?
Logged
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Offline theanonymous

  • Full Member
  • ****
  • Posts: 235
  • Mole Snacks: +1/-14
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
Logged
Pages: [1] 2   Go Up
« previous next »
Sponsored Links