Version A

Theorie (gesloten boek):

1. Calculate the bond force of a nitrile function.
2. Explain the effect of a substituent on a conjugated system. Give three examples and explain them. Draw an energy diagram for two of the three.
3. Draw the off-resonance $^{13}\text{C-NMR}$ spectrum of $N,N$-dimethylbut-2-enamide and explain the shifts.
4. Explain the coupling in an ABX system and give an example.
5. What are the advantages of a stronger magnetic field in NMR spectroscopy and give an example.
6. Give the fragmentation pattern for 4-methyl-4-heptanol for the peaks $m/z = 115, 112, 87, 56$.

Oefeningen (open boek):

Three spectra given, find the correct structure and explain your reasoning. Interpret all spectra except for the UV-spectrum and give the 3 most common fragmentation patterns (from the MS spectrum).

• Oefening 1:

• Oefening 2:

• Oefening 3:

Reeks B

Theorie:

1. Explain conjugation and its effect on the electronic transitions. Describe three types and give the diagrams of two of these types.
2. Calculate the bond force constant of a keto function.
3. Give the drawbacks and advantages of Raman spectroscopy.
4. Draw the $^{13}\text{C-NMR}$ of $N,N$-dimethyl-2-buteenamide and explain the chemical shifts.
5. Give the fragmentation pattern of 4-methyl-4-heptanol, peaks at $m/z = 115, 112, 87$ and $56$.
6. Explain and discuss spin-spin coupling in $^{1}\text{H-NMR}$ of an $\text{AX}_2$ system.

Deel Stevens:

1. Give and comment on the 3 models that predict enantioselective nucleophilic addition to ketones. Apply the theory to the addition of $\text{MeMgBr}$ to $(R)$-2-hydroxy-2-phenylpropiophenone in diethylether.
2. Discuss the Stille coupling.
3. Why is the importance of photochemical reactions in microreactors growing? Give an example and explain the classical problems encountered with photochemical reactions in batch.
4. Discuss the BASIL process and explain the significance of this industrial breakthrough.
5. Describe oxidative addition and reductive elimination. How can these processes be facilitated?

Deel D'hooghe:

6. Discuss the monobromination of 1-methylimidazole.
7. Give the reaction and mechanism for the conversion: $$\text{1-phenylpropan-1-one} \longrightarrow \text{2-amino-1-phenylpropan-1-one}$$
8. Bespreek en werk de mechanismen uit van:
   • Stikstofmosterd
   • Payne-omlegging
   • Semi-benzilzuuromlegging
   • Reactie van $\text{OsO}_4$ op cyclohexeen (noot: $\text{OsO}_4$ was niet expliciet vermeld in de vraagstelling)
9. Discuss 3 different synthetic pathways to prepare aziridines.

Deel Stevens:

1. Give four advantages and four disadvantages of the use of ionic liquids.
2. Give a stereoselective way to convert propionic acid to 2-($S$)-allylpropionic acid.
3. Explain the deconvolution method in combinatorial chemistry.
4. Give and discuss the Suzuki coupling.

Deel D'hooghe:

1. Two small exercises where a structure was given and the question was which reaction would take place (one was a nitrogen mustard and the other one was an epoxide where an aza-Payne reaction could take place).
2. How can cyclopentene be converted to 1-benzylpiperidine using dihydroxylation, oxidative cleavage and reductive amination?
3. Exercise on the Arndt-Eistert reaction.
4. Explain the Simmons-Smith reagent.