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organic chemistry quesitons
#1 Posted : Tuesday, June 29, 2021 5:09:50 PM
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Organic chemistry questions:

1) When CH3 is bonded to Carbon, why is it electron donating? I thought CH3 was not polar and therefore would not contribute to the Electron density? Interested in why a tertiary alcohol is less stable due to the electron donating groups.
2) What is the meaning of an empty p orbital? What does it mean by BF3 having an empty p orbital?
3) Among the carboxylic acid derivatives, where does carboxylic acid fall in the list in terms of reactivity?
4) Because D is classified as +, and R is also classified as +, can we equate D and R as the same? If they give +/- which configuration is it referring to?
5) Question 64 in the chapter 3 practice questions: Why is NO2 a better electron withdrawing group than Cl? When NO2 and Cl both leave they have an overall negative charge and I understand that No2 can form resonance, but cl- would become a noble gas so isn't this more stable?
6) Question 64 in the chapter 3 practice questions: How can you identify the monomers? I thought every peptide bond signifies a monomer, I see three peptide bonds in total?
7) How can you tell if a compound will form a helical or b pleated sheets by looking at its structure?
8) Question 66 in the In class exam #3: I thought compound 1 was the more thermodynamic product because it contains more carbons on either side of the double bond, and therefore would be harder to break requiring a higher activation Energy? EK says compound 1 is the kinetic product and I do not understand why?
#2 Posted : Saturday, July 03, 2021 8:51:30 PM
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Hi Moiz,

1) CH3 is just an addition of more electrons since the atoms are not particularly electron withddrawing, so its slightly electron donating.
2) An empty p orbital just means that there is an empty orbital that an atom is DYING to have filled with two electrons. This is what makes ie. boron so reactive.
3) Good question, I would say between acid and anhydride.
4) No we cannot. R is not considered "+". R is Cahn-Ingold rule applied where as D is referring to the ability to rotate plane polarized light. In essense: R =/= D = +.
5) NO2 is a resonance stabilized structure which will be electron deficient and therefore great at withdrawing. Cl has electronegativity qualities but its not as strong as resonance effect.
6) Yes, every peptide bond signals a monomer. I usually count the C=O groups in the backbone to help.
7) Honestly, there's no good way to tell. There's a whole field in trying to figure out protein structure based on sequence. You'll be told if you need to differentiate.
8) I think there might have been some confusion or perhaps you are looking at an older version of the book, but compound 1 is like you said, thermodynamic product. The answers I am looking at also states the same.

Hope that helps!


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