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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: LuckyDude35 on September 08, 2004, 01:12:47 AM

Title: O chem *delete me*!!!!!!!!! PLEASE
Post by: LuckyDude35 on September 08, 2004, 01:12:47 AM
Ok, I have a question. I have a homework assignment that wants me to decide whether the major reaction is: proton transfer, substitution, or elimination and write them out. I need examples to tell which one to use or maybe a check list approach that I can follow to do the 10 problems. ANY help would be greatly appreciated, thank you very much!
                                        Confused in California
Title: Re:O chem *delete me*!!!!!!!!! PLEASE
Post by: Mitch on September 08, 2004, 01:22:39 AM
Elimination would mean a double bond is formed. Substitution would mean an atom was replaced with an other atom. Perhaps if you posted one of the questions we can work it out with you.
Title: Re:O chem *delete me*!!!!!!!!! PLEASE
Post by: LuckyDude35 on September 08, 2004, 01:27:57 AM
Ok here goes:

bromomethane + hydrogen Sulfide (HS-) in DMF

Thank you very much!
Title: Re:O chem *delete me*!!!!!!!!! PLEASE
Post by: LuckyDude35 on September 08, 2004, 01:30:51 AM
Another one is:

1-methylcyclopentanol + HCL at 0 degrees C

I just don't know how to get started, my teacher didn't give us any examples to go off of. Thank you for your help
Title: Re:O chem *delete me*!!!!!!!!! PLEASE
Post by: Mitch on September 08, 2004, 01:31:22 AM
Out of those 3 compounds are there any good leaving groups in any of them?
Title: Re:O chem *delete me*!!!!!!!!! PLEASE
Post by: LuckyDude35 on September 08, 2004, 01:32:17 AM
Isnt the BR a leaving group?
Title: Re:O chem *delete me*!!!!!!!!! PLEASE
Post by: Mitch on September 08, 2004, 01:34:58 AM
Yes you can kinda tell the Br- is a good leaving group. Can you also tell that the HS- has a lot of electron density around it which makes is a good nuleophile?
Title: Re:O chem *delete me*!!!!!!!!! PLEASE
Post by: LuckyDude35 on September 08, 2004, 01:36:23 AM
I thought it was a good nucleophile but wasn't sure, so that means this is a SN1 or SN2 reaction?
Title: Re:O chem *delete me*!!!!!!!!! PLEASE
Post by: Mitch on September 08, 2004, 01:40:09 AM
Which one, SN1 or SN2, likes to have the carbon be least substituted with other R-groups?
Title: Re:O chem *delete me*!!!!!!!!! PLEASE
Post by: LuckyDude35 on September 08, 2004, 01:41:47 AM
I know the SN2 is primary, so SN2?
Title: Re:O chem *delete me*!!!!!!!!! PLEASE
Post by: Mitch on September 08, 2004, 01:43:01 AM
Yes,  I think you understand the material just sit down with it and if you still have some questions go ahead and ask them.
Title: Re:O chem *delete me*!!!!!!!!! PLEASE
Post by: LuckyDude35 on September 08, 2004, 01:46:05 AM
To be perfectly honest I feel like I have no idea what I am doing with some of these. I saw the DMF, and I know that is polar aprotic and i know that is supposed to be SN2, does that mean that all the one with DMF are SN2?
Title: Re:O chem *delete me*!!!!!!!!! PLEASE
Post by: LuckyDude35 on September 08, 2004, 01:57:55 AM
I drew out the equation and have a question, does the Br which left then attach to the H which was now alone after the S substituted for the BR?
Title: Re:O chem *delete me*!!!!!!!!! PLEASE
Post by: Mitch on September 08, 2004, 03:29:00 AM
No, the S is still attached to the S. We did no Chemistry to remove it from the S.