Reference no: EM132579386

Short Answer (you must show all of your work to receive full credit for the following questions)
1. (a) Draw the structures of the five constitutional isomers having the molecular formula C6H14.
(b) For each of your structures, provide a name that conforms to the IUPAC system of nomenclature.

2,3,4: Using the curved-arrow formalism, provide a mechanism that accounts for the formation of 1,2,3. For full credit, you must show each individual step in the mechanism.

5. Provide an explanation for the following two observations: When 4 is treated with ethoxide in ethanol, the rate of formation of 5 does not change appreciably as the concentration of ethoxide is increased. Nonetheless, increasing the concentration of ethoxide does cause a marked increase in the rate at which 4 disappears from the reaction mixture. As part of your answer, identify by which mechanism(s) (SN2, SN1, E2, E1) 5 and 6 form.

6.Identify each of the following functional groups

7. Resonance Structures
(a) For each of the following pairs, identify which of the resonance structures contributes more to the resonance hybrid. Provide a justification for your selections.
(b) Explain why 8 and 9 are not valid resonance structures of 7.

8. Based on the free energy diagram answer the questions below:
a) Which product is the kinetic product?
b) Which product is the thermodynamic product?
c) Are the reactions exergonic or endergonic?

9. Consider molecule
(a) How many unique 1H environments are present in 10?
(b) How many unique 13C environments are present in 10?
(c) What is the spin-spin splitting pattern for environment Ha?
(d) What is the spin-spin splitting pattern for environment Hb?

10. When 11 reacts with H2O, multiple products are formed via carbocation intermediates
(a) Draw the structures of 4 possible substitution and/or elimination products that result from carbocation intermediate 12 (assume no carbocation rearrangement occurs).
(b) Draw the structures of 4 possible substitution and elimination products that result from carbocation intermediate 13 (assume no carbocation rearrangement occurs).
(c) Are substitution or elimination products likely to dominate under these conditions?

11. Assign an R or S configuration to each of the following molecules

12. Provide a structure or example for each of the following.
(a) a gauche conformation of butane
(b) two p orbitals overlapping to form a pi (π) bonding molecular orbital
(c) a chair conformation of methylcyclohexane (methyl group in axial position)
(d) a hydrogen bond between two molecules of ammonia (NH3)
(e) a secondary alcohol

13. Determine whether each of the following molecules is chiral or achiral

14. For each of the following reactions, provide the structure (including stereochemistry) of the major organic product. If no products are expected, indicate that the reaction does not proceed (NR)

15. Provide the structure of an organic molecule that is most consistent with the given analytical and spectroscopic data. Show as much of your reasoning as possible