1. (i) Draw Newman projections for the 6 rotational isomers of 3-methylpentane visualizing down the C2-C3 bond. (i) Draw the energy diagram for a 360 deg rotation about this bond, indicating the relative energies of the 6 species.
2. (i) Draw the two chair conformations for trans-2,3-dimethylcyclohexane. (ii) Draw the two chair conformations for cis-2,3-dimethylcyclohexane. (iii) Which isomer is more stable and why?
3. For the following, determine if the atoms (indicated by the arrow) are electrophilic, nucleophilic, or neither.
![1191_Draw Newman projections.png](https://secure.tutorsglobe.com/CMSImages/1191_Draw%20Newman%20projections.png)
4. Propose reasonable mechanism for the following transformation using curved arrow notation.
![1406_Draw Newman projections1.png](https://secure.tutorsglobe.com/CMSImages/1406_Draw%20Newman%20projections1.png)
5. Provide the major product for the following reactions. Use curved arrow notation to indicate the flow of electrons.
![1502_Draw Newman projections2.png](https://secure.tutorsglobe.com/CMSImages/1502_Draw%20Newman%20projections2.png)
6. (i) Draw a mechanism using curved arrow notation for the acid-catalyzed cleavage (hydrolysis) of the following molecule.
![1628_Draw Newman projections3.png](https://secure.tutorsglobe.com/CMSImages/1628_Draw%20Newman%20projections3.png)
(ii) Synthesize the following molecule using the appropriate carbonyl compound.
![1323_Draw Newman projections4.png](https://secure.tutorsglobe.com/CMSImages/1323_Draw%20Newman%20projections4.png)
7. The beta-blocker atenolol is commonly prescribed for high blood pressure and is used to slow the heart rate of patients at risk for "a-fib". The molecular structure is shown below.
![1718_Draw Newman projections5.png](https://secure.tutorsglobe.com/CMSImages/1718_Draw%20Newman%20projections5.png)
a. What is the molecular formula?
b. Circle and name all functional groups present.
c. Provide bond descriptions for bonds a and b.
d. Give the hybridization of carbon c and oxygen d.
e. Explain how the hybridization of carbon c occurs.
f. Draw the VB representation (orbital overlap) of the bonds shown below.
![596_Draw Newman projections6.png](https://secure.tutorsglobe.com/CMSImages/596_Draw%20Newman%20projections6.png)
8. For the following acid base reactions, (a) write the expected products, (b) label all acids and bases and their conjugates, (c) estimate the pKa values, and (c) predict the direction of the equilibrium.
![309_Draw Newman projections7.png](https://secure.tutorsglobe.com/CMSImages/309_Draw%20Newman%20projections7.png)
9. In the following chiral pharmaceuticals, indicate ALL stereocenters with an asterisk (*) and assign the absolute configuration (R or S).
![152_Draw Newman projections8.png](https://secure.tutorsglobe.com/CMSImages/152_Draw%20Newman%20projections8.png)
10. Explain the following observation. Be sure to include resonance structures in your discussion and use structures where appropriate.
![899_Draw Newman projections9.png](https://secure.tutorsglobe.com/CMSImages/899_Draw%20Newman%20projections9.png)