O-Chem Question

[Balsawood201]

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O-Chem Kaplan Test #4 Q1. I am having a little trouble justifying the answer that Kaplan says is correct. I think there may be a mistype in the problem... if not can someone give me a quick explanation of it?

Question says rank the following in increasing basicity:

A -- Analine

B -- Ammonia

C -- Trimethylamine

D -- p-nitro-analine , Even though it says p-nitro-analine for the name m-nitro-analine is drawn

Answer key says D, A, B, C

Thanks

 

[aznnytezx]

Where do you get the Kaplan tests from?

 

[MrSummerlin]

O-Chem Kaplan Test #4 Q1. I am having a little trouble justifying the answer that Kaplan says is correct. I think there may be a mistype in the problem... if not can someone give me a quick explanation of it?

Question says rank the following in increasing basicity:

A -- Analine

B -- Ammonia

C -- Trimethylamine

D -- p-nitro-analine , Even though it says p-nitro-analine for the name m-nitro-analine is drawn

Answer key says D, A, B, C

Thanks

This is just what goes through my mind it doesnt mean its right.

D is the lease basic since it would have a + on the NH3 and a + on the carbon the NH3 attaches to when resonance is taken into account. the + on the C is caused by the NO2 when resonance is taken into account. Also with two deactivating groups on a benzene ring it would make the ring have a lower density of electrons thus destabilizing the ring more than just one deactivating groups in option A.

A is next because the + is deactivating the ring again.

B- Doesnt have a ring to worry about so it better off than the two options with benzene rings but not as good as a tertiary N

C- is the most basic be the + N can delocalize that + charge with the help of the 3 methyl groups attached