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The State University of New York at Binghamton (Binghamton University, BU) 1)For the following empirical formulae, indicate the hybridization of the bolded atom, and the shape of the molecule

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The State University of New York at Binghamton (Binghamton University, BU)

1)For the following empirical formulae, indicate the hybridization of the bolded atom, and the shape of the molecule.

2. Draw the following molecules according to their predicted molecular shape.  Circle the molecules that are POLAR.   
3. The molecule below has a known boiling point.  On the left draw an isomer of the given molecule that should have a lower boiling point.  On the right, draw an isomer that has a higher boiling point.(8)
4. Circle the solvent(s) from the list that would be able to dissolve both water and cyclohexane.

 

5. Indicate the formal charge for the following compounds.
6. Draw all the constitutional isomers for C₅H₁₁F.  There are (8) of them. (you do not have to show the hydrogens)
    

 

 

7. Follow the directions for each of the following ranking problems. 
8. Draw the most stable isomer of C₇H₁₆.
9. Using curved arrow notation, draw the resonance structure(s) for the following 3 compounds.  In the box on the right show the resonance hybrid.
10. Indicate whether the given orbital makes sigma (s) or pi (p) type bonds or both (b).

 

11. Briefly explain why the C-C bond distance is shorter in an alkyne than in an alkane.
12. Write the name of 6 of the 8 circled functional groups below in the appropriate box provided.
13. Express the substituted chair form drawing on the given cyclohexanes using appropriate symbols.

 

14. Express the given substituted cyclohexane ring forms on the provided chair forms using appropriate notation.(2 forms provided in case you need them.

 

15. A pentagon has bond angles of 108°, but even though this is close to the ideal angle of a sp³ hybridization cyclopentane is not a flat molecule. 
16. Compound p experiences more van der Waals (steric) strain than compound q.  Briefly explain why.

 

17. Follow the directions found at the headings of the 3 columns (20)
18. The reaction below can proceed by either S_N1 or S_N2 pathway.  Pick one pathway. A. Show the step-wise mechanism of the reaction, including the initial acid base reaction with HBr.  B. Using key words defend why it could go by the pathway you chose. (21)

           

 

 

 

 

 

 

 

 

 

19. Since catalysts just lower the energy barrier for a reaction.  Name a likely cause for the rearrangement below. 

 

20. For each of the following examples write the major reaction type to the right of the molecule.