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1. Provide the real name (IUPAC name) for each of the following structures.

280_Figure.png

2. Label the following as aromatic (A), anti-aromatic (AA) or non-aromatic (NA).

2340_Figure1.png

3. Assume you are carrying out a reduction reaction of cyclohexanone to give cyclohexanol product as shown below; describe how you will use the following techniques to monitor the reaction:

89_Figure2.png

a. 1H NMR

b. IR

4. From the structure shows below, calculate the multiplicities of proton signals at positions labeled a, b and c.

1671_Figure3.png

5. Write the number of signals (peaks) expected on (a) 13C NMR and (b) 1H NMR spectra of the following compound.

586_Figure5.png

6. Provide the product (and stereochemistry) for the Diels-Alder reactions.

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7. Provide the family names of the following compounds.

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8. Which will be a stronger acid? Explain why it is stronger.

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9. Give the fragmentation products of the compounds shown below.

798_Figure9.png

10. The following compounds al show a single line in their 13C NMR spectra. Use numbers 1-4 to label them in their expected order of increasing chemical shifts.

1049_Figure10.png

11. Provide the product in the following reactions.

1225_Figure11.png

12. Provide the products for the following reactions.

1925_Figure12.png

13. Label each statement as "True" or a "False".

- Deshielding results in the chemical shift signal moving further down field.

- Deshielding results in the chemical shift signal moving further up field.

- Deshielding results in the chemical shift signal moving further to the left.

- Deshielding results in the chemical shift signal moving further to the right.

- Deshielding results in the reduction of electron density around the proton nuclei.

- Deshielding results in the increase of electron density around the proton nuclei,

- Homotopic protons have same chemical shift values.

- Enantiotopic protons have same chemical shift values.

- Diastereotopic protons have same chemical shift values.

- Kinetic products are less stable than thermodynamic products.

- Kinetic products are more stable than thermodynamic products.

- Epoxides are also ethers.

- Alcohols are more acidic that carboxylic acids.

- One problem with Friedel-Crafts acylation is the rearrangement of the carbocation intermediate.

- Carboxylate ions are more stable then alkoxide ions.

14. Identify the main functional group present in the spectrum below.

2263_Figure14.png

15. For the spectrum below, provide the following:

93_Figure15.png

a. M+ ion

b. Base ion

c. Parent peak

d. Molecular peak

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