CHEM 232 Exam 4 with 100% Correct
Answers
transform alkene to single bond with 2 hydrogens (RXN TYPE 1) - ANS-
HYDROGENATION
reagents: H2 + Pd/C or Pt metal
transform alkene to single bond with a X added to the more substituted carbon and a H
to added to the less substituted carbon (RXN TYPE 2)
Markovnikov - ANS-HYDROHALOGENATION
reagents: nucleophilic acid like HCl or HBr
transform alkene to single bond with an alcohol (OH) added to the more substituted
carbon (RXN TYPE 2)
Markovnikov - ANS-HYDRATION
reagents: strong acid like cat. H2SO4 + H2O solvent
shift the location of alkene or change the orientation of groups around alkene (RXN
TYPE 2)
E1: zaitsev - ANS-ALKENE ISOMERIZATION
reagent: cat. H2SO4
transform alkene to single bond with a halogen bonded to each carbon (RXN TYPE 3)
ANTI- addition - ANS-HALOGENATION
reagent: X2= Cl2 or Br2
transform alkene to single bond with a halogen on the less substituted carbon and an
alcohol on the more substituted carbon (RXN TYPE 3)
ANTI- addition - ANS-HALOHYDRIN SYNTHESIS
reagents: X2 + H2O or ROH
transform alkene to single bond with either an alcohol or ether bonded to the more
substituted carbon (RXN TYPE 3)
ANTI- addition
Markovnikov - ANS-OXYMERCURATION-REDUCTION
, reagents: 1.) Hg(OAc)2 + HOH or HOR 2.) NaBH4 + NaOH
transform alkene to single bond with an alcohol bonded to the less substituted carbon
(RXN TYPE 3)
SYN-addition
Anti-Markovnikov - ANS-HYDROBORATION-OXIDATION
reagents: 1.) BH3 or B2H6 2.) H2O2 + NaOH
transform alkene into the epoxide (RXN TYPE 3)
SYN-addition - ANS-EPOXIDATION
reagents: mCPBA or peracetic acid or trifluoroperacetic acid
transform alkene into a single bond with an alcohol bonded to each carbon (cis addition)
(RXN TYPE 4)
vicinal diols - ANS-SYN-DIHYDROXYLATION WITH OSO4
reagents: 1.) OsO4. 2.) H2S or Zn
another option: 1.) cat. OsO4 w/ amine oxide, H2O, acetone
transform alkene into two carbonyl groups (either ketone and aldehyde or ketone and
carboxylic acid) (RXN TYPE 4)
only reaction that allows us to break C-C bond - ANS-OZONOLYSIS
reagents: 1.) O3 (ozone) 2.) either S(CH3)2 or H2O2/H2O depending on whether it's
reducing or oxidizing
transform an alkyne into a nucleophile and form a new C-C bond (RXN TYPE 1: Alkyne)
- ANS-ALKYL HALIDE
reagents: NaNH2 or NaH (activates acetylide) and alkyl halide (electrophile)
transform alkyne into single bond with 2 H's added to each carbon (RXN TYPE 2:
Alkyne) - ANS-REDUCTION VIA CATALYTIC HYDROGENATION
reagents: H2 + Pd/C or Pt metal
transform alkyne into alkene with a H added to each carbon in a cis conformation (RXN
TYPE 2: Alkyne)
SYN addition - ANS-PARTIAL REDUCTION: HYDROGENATION W/ LINDLAR'S
CATALYST
reagents: H2, Pd/CaCO3, Pb(OAC)2, quinoline
transform alkyne into alkene with a H added to each carbon in a trans conformation
(RXN TYPE 2: Alkyne)
Answers
transform alkene to single bond with 2 hydrogens (RXN TYPE 1) - ANS-
HYDROGENATION
reagents: H2 + Pd/C or Pt metal
transform alkene to single bond with a X added to the more substituted carbon and a H
to added to the less substituted carbon (RXN TYPE 2)
Markovnikov - ANS-HYDROHALOGENATION
reagents: nucleophilic acid like HCl or HBr
transform alkene to single bond with an alcohol (OH) added to the more substituted
carbon (RXN TYPE 2)
Markovnikov - ANS-HYDRATION
reagents: strong acid like cat. H2SO4 + H2O solvent
shift the location of alkene or change the orientation of groups around alkene (RXN
TYPE 2)
E1: zaitsev - ANS-ALKENE ISOMERIZATION
reagent: cat. H2SO4
transform alkene to single bond with a halogen bonded to each carbon (RXN TYPE 3)
ANTI- addition - ANS-HALOGENATION
reagent: X2= Cl2 or Br2
transform alkene to single bond with a halogen on the less substituted carbon and an
alcohol on the more substituted carbon (RXN TYPE 3)
ANTI- addition - ANS-HALOHYDRIN SYNTHESIS
reagents: X2 + H2O or ROH
transform alkene to single bond with either an alcohol or ether bonded to the more
substituted carbon (RXN TYPE 3)
ANTI- addition
Markovnikov - ANS-OXYMERCURATION-REDUCTION
, reagents: 1.) Hg(OAc)2 + HOH or HOR 2.) NaBH4 + NaOH
transform alkene to single bond with an alcohol bonded to the less substituted carbon
(RXN TYPE 3)
SYN-addition
Anti-Markovnikov - ANS-HYDROBORATION-OXIDATION
reagents: 1.) BH3 or B2H6 2.) H2O2 + NaOH
transform alkene into the epoxide (RXN TYPE 3)
SYN-addition - ANS-EPOXIDATION
reagents: mCPBA or peracetic acid or trifluoroperacetic acid
transform alkene into a single bond with an alcohol bonded to each carbon (cis addition)
(RXN TYPE 4)
vicinal diols - ANS-SYN-DIHYDROXYLATION WITH OSO4
reagents: 1.) OsO4. 2.) H2S or Zn
another option: 1.) cat. OsO4 w/ amine oxide, H2O, acetone
transform alkene into two carbonyl groups (either ketone and aldehyde or ketone and
carboxylic acid) (RXN TYPE 4)
only reaction that allows us to break C-C bond - ANS-OZONOLYSIS
reagents: 1.) O3 (ozone) 2.) either S(CH3)2 or H2O2/H2O depending on whether it's
reducing or oxidizing
transform an alkyne into a nucleophile and form a new C-C bond (RXN TYPE 1: Alkyne)
- ANS-ALKYL HALIDE
reagents: NaNH2 or NaH (activates acetylide) and alkyl halide (electrophile)
transform alkyne into single bond with 2 H's added to each carbon (RXN TYPE 2:
Alkyne) - ANS-REDUCTION VIA CATALYTIC HYDROGENATION
reagents: H2 + Pd/C or Pt metal
transform alkyne into alkene with a H added to each carbon in a cis conformation (RXN
TYPE 2: Alkyne)
SYN addition - ANS-PARTIAL REDUCTION: HYDROGENATION W/ LINDLAR'S
CATALYST
reagents: H2, Pd/CaCO3, Pb(OAC)2, quinoline
transform alkyne into alkene with a H added to each carbon in a trans conformation
(RXN TYPE 2: Alkyne)
