1. Predict which of the following compounds would be the strongest acid.

2. For 1H-NMR peak that is a doublet with an integral of 3 H at 1
For 1H-NMR peak that is a doublet with an integral of 3 H at 1.21 ppm what do we know? 1 2 3 4 5 6 7 8 9

3. Assign the priority according to the Cahn-Ingold-Prelog convention.

4. triplet singlet doublet quartet sextet
What is the multiplicity of the signal for the hydrogens at the indicated position?
triplet
singlet
doublet
quartet
sextet

5. How many of the following compounds are chiral?1 2 3 4

6. How many sp2 hybridized C’s are present in the following structure?5 6 7 8 9

7. In an sp3 hybridized carbon, how many sp3 hybrid orbitals are there?1 2 3 4

8. Predict the major product of the following reaction.

9. Two singlets Two doublets Four singlets Four doublets
What would you expect to see in the 1H NMR in the aromatic region for 4-bromotoluene.
Two singlets
Two doublets
Four singlets
Four doublets

10. Rank the following from most nucleophilic to least nucleophilic.
HO- H2O H2N- H3N

11. Rank the following carbocations from most stable to least stable.

12. What is the electron configuration of N?
1s22s22p3
1s22s22p4
1s22s12p3

13. What is the hybridization on carbon 1?sp
sp2
sp3
sp4

14. What is the electronic geometry at carbon 1?
a. linear b. trigonal planar c. trigonal pyramidal d. tetrahedral

15. Classify the carbocation as
a. 1 b. 2 c. 3 d. 4

16. Generic Questions
Which of the following compounds represents the enantiomer of _____________?
Which of the following compounds are the same? (Draw various representations.)
Which of the following protons is most deshielded?
Where would you look in the IR to confirm that a reaction took place?