[aspiringphysician]

Long time, no see...I haven't been on here for almost a year!

I haven't touched a Chemistry book since last summer, but now I'm ready to dive back in and review all the Chemistry I've learned as an undergraduate, in preparation for the MCAT!

I am using the Berkeley Review MCAT study books. I have a few Organic Chemistry questions that have come up over the last few days of reviewing:

1) In which cases does resonance "trump" the inductive effect? (Sorry in advance if this question is too generic or vague.)

2) What are 1°, 2°, 3°, and 4° carbons? (I'm ashamed I don't remember this...)

3) My study book states that an amine lone pair binds the protic hydrogen of an alcohol more tightly than an alcohol lone pair binds the protic hydrogen of an amine, but the book goes on to say that hydrogen bonding in alcohols is stronger than in amines. To me, these statements contradict each other, but I'm probably interpreting something wrong. Could someone please explain this to me in simpler terms?

Thanks in advance for your *delete me* 

~ AP ~

[TheOrganic]

You need to go back to your books and read. My guess is that your score will improve a lot if you at least brush up general chemistry and general organic chemistry very well.

As for the questions, I will help but not answer them all.

1) This question is too generic and vague, as you pointed out. It's impossible to give a general answer.

2) 1° carbon atom means if has only one carbon substituent directly attached to it. 2° means two carbon substituents and so on. You also need to brush up the trivial names for such carbons. 2° position is often called isopropyl position, 3° position is often called tertiary butyl position, 4° position is often called neopentyl position.

3) I think this is simple. The lone pairs on both the amine and the oxygen are in the same "energy level".
Look at your question - you want to compare whether Nitrogen holds protons better or Oxygen. Shouldn't the intranuclear protons of oxygen ( greater atomic number ) repel the proton more? In that case, Ammonia should be binding it more tightly.