Exam 4 Flashcards
Acetylide anions undergo Sn2 reactions with what degree substituted alkyl halide?
Primary (1’)
Acetylide anions undergo E2 reactions with what degree substituted alkyl halide?
Secondary and tertiary (2’ and 3’)
Terminal alkynes are readily converted to acetylide anions with strong bases such as NaNH2 and NaH.
These undergo Sn2 reaction for 1’ alkyl halides, and E2 reactions for 2’ and 3’ alkyl halides
True/False: Acetylide anions are strong nucleophiles that open epoxide rings by an SN2 mechanism.
True
What is another name for the product of a synthesis reaction?
Target compound
What are the two categories used to design a synthesis?
1–Those that form new carbon–carbon bonds. 2–Those that convert one functional group into another—that is, functional group interconversions.
What is a tautomer?
Tautomers are constitutional isomers that differ in the location of a double bond and a hydrogen atom. Two tautomers are in equilibrium with each other.
What is an enol tautomer?
An enol tautomer has an O—H group bonded to a C==C.
What is an keto tautomer?
A keto tautomer has a C=O and an additional C—H bond.
What does it mean to be acid catalyzed in a reaction?
When the acid used to protonate an enol in step 1, is reformed in step 2
When acetylide anions (which are strong Nu-) open epoxide rings via Sn2, which carbon do they attack ?
The least substituted carbon
True/False: Two tautomers are in equilibrium with eachother
True
What does the addition of H2O using H2O, H2SO4, and HgSO4 form?
methyl ketones from terminal alkynes
What does the addition of H2O using BH3, then H2O2, HO form?
aldehydes from terminal alkynes
Primary (1’) alcohols are oxidized to ______ or ______
Aldehydes or Carboxylic acids