Functional Groups & Reactions

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

Just state what molcule is deprotonated

Water (H2O)

Answer: B

A. Add a fractionating column

B. palce receiving flask in an ice bath

D. Connect distillation setup to a vacuum

Answer A

Ester, Anhydride, Amide or Enamine

Amide

blactam rings —> angle strain (less than 109.5º)

or

B lactam can participate in more resonance

ANswer; A

Cyanohydrin

Answer D

C. The hemiketal—OH group cannot be protonated under basic conditions to make a good leaving group for the ketal to form

D. The hemiacetal—Oh group cannot be protonated udner basic conditions to make a good leaving group for the acetal to form

L, D, R, S

S configuration

(lets focus on aldehyde)

a branched aldehyde with same molecular weight

Answer: D

Carboxyl group

Functional group examples

Answer C

will the product or Hexanoic acid distill first?

Product will distill first because hexanoic acid has higher boiling point

A. base catalyzed aldol condensation

B. Decarboxylation

C. Oxidation with NaBH4

D.Reduction with LiAlH3

Answer: D

L, D, or Mix?

Mix

15 minute mark

boiling point (lowest to highest)

ethane < Acetaldehyde < ethanol + ethyl acetate < Acetic acid

Number 1

Oxidation of alchohols