From the structure shows below calculate the multiplicities

Question

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

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

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:

a. ¹H NMR

b. IR

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

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

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

7. Provide the family names of the following compounds.

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

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

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.

11. Provide the product in the following reactions.

12. Provide the products for the following reactions.

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.

15. For the spectrum below, provide the following:

a. M⁺ ion

b. Base ion

c. Parent peak

d. Molecular peak