Comments on: How do you get from here to there....?
http://ask.metafilter.com/139964/How-do-you-get-from-here-to-there/
Comments on Ask MetaFilter post How do you get from here to there....?Sun, 06 Dec 2009 16:12:16 -0800Sun, 06 Dec 2009 16:12:16 -0800en-ushttp://blogs.law.harvard.edu/tech/rss60Question: How do you get from here to there....?
http://ask.metafilter.com/139964/How-do-you-get-from-here-to-there
Organic Chemistry filter: I just want to make sure I'm doing this right... <br /><br /> Yes, this is a homework problem. I admit it freely. But I put the time into it, and just want to make sure that I'm on the right track. I think I have it right. It seems pretty straightforward. If anyone can tell me if I am not thinking about it right or if I am on the right track, I would really appreciate it.<br>
<br>
The problem: provide syntheses (should take 3 steps) to get from 1-butanol to hexene, from only the starting material and reagents or compounds with 2 carbons or less.<br>
<br>
My answer: <br>
Step 1: I used PBr3 to turn 1-butanol into 1-bromo butane + HoPBr2.<br>
Step 2: I used an ethyne anion (via E2) to turn the 1-bromo butane <br>
into 1-hexyne. <br>
Step 3: I used 2 mol of H2 and a Pd catalyst to convert the <br>
1-hexyne to hexene.<br>
<br>
I hope I did this right! Can someone please let me know, and if not, tell me what direction to look in? Thank you!post:ask.metafilter.com,2009:site.139964Sun, 06 Dec 2009 14:33:48 -0800bolognius maximusorganicchemistrysynthesisBy: d. z. wang
http://ask.metafilter.com/139964/How-do-you-get-from-here-to-there#2001769
Two equivalents of hydrogen gas will bring it down to hexane. There are other techniques for a partial hydrogenation.comment:ask.metafilter.com,2009:site.139964-2001769Sun, 06 Dec 2009 16:12:16 -0800d. z. wangBy: bolognius maximus
http://ask.metafilter.com/139964/How-do-you-get-from-here-to-there#2001806
Oops, my bad. That was a typo. Thanks!comment:ask.metafilter.com,2009:site.139964-2001806Sun, 06 Dec 2009 16:46:19 -0800bolognius maximusBy: Dr.Enormous
http://ask.metafilter.com/139964/How-do-you-get-from-here-to-there#2001809
You have it basically down, but for some nitpicks:<br>
<br>
1. S<sub>N2, not E2. E2 is elimination.<br>
2. You can't stop hydrogenation by limiting equivalents. You have to do it by reagent (using Lindlar's catalyst or Li/NH<sub>3</sub>).</sub>comment:ask.metafilter.com,2009:site.139964-2001809Sun, 06 Dec 2009 16:51:33 -0800Dr.EnormousBy: bolognius maximus
http://ask.metafilter.com/139964/How-do-you-get-from-here-to-there#2001929
Original problem should have said convert to hexane instead of hexene, my bad. Thanks for the suggestions.comment:ask.metafilter.com,2009:site.139964-2001929Sun, 06 Dec 2009 18:49:25 -0800bolognius maximus