Questions and problems

a$)$ Mark and name all functional groups of Trifarotene. If applicable, state

whether they are primary, secondary or tertiary. You may want to use appendix$1.$

b$)$ Explain whether Trifarotene contains any functional group that are relevant for acid$-$base chemistry. Is Trifarotene an acid, a base or an ampholyte?

c$)$ Draw the structure of the product in a reaction where Trifarotene is oxidized by a mild oxidation agent like pyridinium chlorochromate $($PCC$).$

d$)$ Draw the structure of the product in a reaction where Trifarotene is reduced by LiAlH$4.$

e$)$ Explain how many different signals we would expect in the $13$C$-$NMR spectrum of Trifarotene.

f$)$ Provide the systematic name of Compound $1$ according to IUPAC nomenclature rules.

g$)$ Provide the reaction type of the reaction where Compound $1$ and Compound $2$ react. Then, use curved arrows to show the reaction mechanism.

h$)$ Provide the reaction type of the reaction where Compound $3$ is converted to Trifarotene. Then, use curved arrows to show the reaction mechanism.

Tretinoin and Alitretinoin are stereoisomers. They differ only in the configuration around one C$-$C double bond.

i$)$ Are Tretinoin and Alitretinoin enantiomers? Identify the C$-$C double bond where the configuration is different in the two molecules and explain which

is $($E$)$ and which is $($Z$).$