Functional Group

Answer A

Passage A

Tyr, Phe, Trp, Pro?

Pro

Gabriel Synthesis // Malonic ester synthesis

B. Gabriel Syn results in a mixture of enantionmers, and the catalyst used in the Hajos Parrish reaction is a single enantiomer

C. GS results in the S enantiomer, and the catalyst used in the HP reaction is R enantiomer

D. (flip the S and R order in answer C)

Answer: B

Vinyl vs allyl group

B. By using a resolving agent to create a mixture of diastereomers, which can be separated due to ahving different chemical properties

D. Separate the mixture of enantiomers obtained fromt eh reaction using column chromatography with a chiral stationary phase

Answer: D

3

Answer: 4

Adol condensation

carbon carbon bond forming reactions where two carbonyl compoudns (ketones and/or aldehydes) are joined together by nucleophilic additon to form the adol product.

Adol condensation true or false based on a passage

1. reaction ahs two carbonyl compounds as substrates

2. reaction involves protonation of a bcarbon for elimination

3. reaction has resonance stabilized intermediate

4. reactions yields a conjugated product

1. true

2. flase

3. true

4. true

Answer A

Answer D

Note: ALL amino acids EXCEPT cysteine has a S configuration. The S form of most amino acids is the L form (except cys R-L)

so answer is B

Clockwise—> R—> but H is wedge in front—→ flip—→ S configuration

Answr D

Abnswer B

nucleophilic addition, nucleophilic elimination, nucleophili acyl substitution, Sn2?

nucleophilic acyl sub

Carbonyl carbon in B is more electrophilic than Carbonyl carbon in compound D

Or

Carbonyl carbon in Compound B is less sterically hindered than D

2

Lactonization

intramolecular reaction between alcohol and carboylic acid to form lactone ( cyclic ester)

Lactamization

intramolecular condensation reaction between amine and carboxylic acid to form lactam (cyclic amide)

What is the chemical transformation?

Hydrolysis, lactonization, reduction, or lactamization?

Answer: D

Lovastatin

Note electronic effect vs steric effect

aldol condensation or aldol addition?

adol addition

Answer D