Author Topic: Acid/base confusion (organic chemistry)  (Read 4268 times)

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Offline Ħ

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Acid/base confusion (organic chemistry)
« on: October 10, 2011, 03:38:44 PM »
Okay, so I'm having a lot of trouble with this.  I "get" it, but I don't.  So maybe someone can help me out.
 
Here's the molecules we are given (apologies for not drawing it out):
 
1) CH2O
2) CH3-
3) Zn2+
4) H2O
5) AlCl3
6) CH3+
7) CH3Cl
8) OH-
9) HCl
10) Br-
 
And the questions are:
 
Which are Bronsted-Lowry acids? (2 of the above)
Which are Lewis Acids? (3 of the above)
Which have an electrophilic carbon? (3 of the above)
Which are nucleophiles? (5 of the above)
T or F - are all nucleophiles Lewis bases?
T or F - are all electrophiles Lewis acids?
 
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I understand that BL acids are proton donaters...but doesn't that technically mean that there are multiple answers?  I suppose it just wants the best BL acids.  Which (I think) are HCl and CH3+.
 
As for Lewis acids...I'm stumped.  I guess I would just go with HCl and CH3+ again, and maybe add Zn2+?
 
Totally confused with the other stuff, though.
 
 
Due in an hour and twenty minutes!
"All great works are prepared in the desert, including the redemption of the world. The precursors, the followers, the Master Himself, all obeyed or have to obey one and the same law. Prophets, apostles, preachers, martyrs, pioneers of knowledge, inspired artists in every art, ordinary men and the Man-God, all pay tribute to loneliness, to the life of silence, to the night." - A. G. Sertillanges

Offline Ħ

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Re: Acid/base confusion (organic chemistry)
« Reply #1 on: October 10, 2011, 04:00:36 PM »
Anybody? :sadpanda:
"All great works are prepared in the desert, including the redemption of the world. The precursors, the followers, the Master Himself, all obeyed or have to obey one and the same law. Prophets, apostles, preachers, martyrs, pioneers of knowledge, inspired artists in every art, ordinary men and the Man-God, all pay tribute to loneliness, to the life of silence, to the night." - A. G. Sertillanges

Offline XianL

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Re: Acid/base confusion (organic chemistry)
« Reply #2 on: October 10, 2011, 04:35:42 PM »
Will take time out of working on my Materials Science Lab report to help :P

Q1: Likely 4 and 9. Water, albiet a weak base, can nontheless lose a H+ without too much hassle, and the Hydrochloric Acid, being one of the so-called "strong acids" is more than happy to lose a proton.

Q2: 3, 5, 6. In terms of accepting lone pairs, a metal cation and a carbocation are prime subjects. Not too sure about Aluminum Trichloride, but like Boron, I'm guessing it can easily accept a lone pair.

Q3: 1, 6, 7. Out of the four carbon species in the list, the only one that ISN'T electrophilic (electron-loving) is 2. So, 1, 6, 7.

Q4: 2, 4, 8, 9, 10. All chosen because they have a lone pair, the main requirement for being a nucleophile. Not necessarily a GOOD nucleophile, but can be.

Q5&6: Hard to answer. Usually when a prof asks this they expect you to find a nucleophile that ISN'T a lewis base or an electrophile that ISN'T a lewis acid. I'd go for T T if I were you.

Edit: Not saying ANY of these answers are right. Just...my best go at it.

Offline Phoenix87x

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Re: Acid/base confusion (organic chemistry)
« Reply #3 on: October 10, 2011, 04:42:33 PM »
For me to properly explain this I would need like 35 minutes of thinking, since Acids/Bases used to confuse me as well. I have studying to do myself so I apologize for being brief.

Not sure about the first question (always had trouble with bronstead lawry)

question 2 Lewis acids

Zn2+ and CH3+         Ch3+ definitely as it wants electrons to balance out its + charge. Molecules DO NOT want charges. I think zn2+ is as well 

Lewis acids accept electrons
Lewis Bases donate electrons

Electrophiles desire electrons (AKA negative charge of any kind) Electrophile literally means "electron Loving" (Seriously)
Nucleophiles are attracted to positive charges, usually carbocations.

which are nucleophiles?

1) CH2O   2) CH3-  4) H2O  8) OH-   10) Br-

Which have an electrophillic carbon?

6) CH3+
7) CH3Cl   These two for sure since ch3 is a carbo cation is inherently an electrophile and Ch3cl has cl which is one of the best leaving groups which you will learn about in sn1 and sn2 reactions.

I would say false to both the T/F questions because I think H20 can act as both and electrophile and nucleophile. I know it can act as both base or acid.

Organic Chemistry all comes down to stability of charges. That's kind of the best way of thinking about it.

once again I apologize for not explaining this in more depth, but it would probably take me an hour to really explain the theory and I am under the gun at the moment. If you have questions in the future, feel free to post them. Hope this helps.