CHEM 233 FINAL REACTIONS REVIEW QUESTIONS AND
CORRECT DETAILED ANSWERS (VERIFIED ANSWERS)
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reactants: alkene + acid Ans✓✓✓Steps: pi bond "grabs" hydrogen,
carbocation intermediate, reaction with anion
Product: racemic mixture of anion on previously double bonded carbon
with more stable carbocation intermediate
reactants: alkene + water in acid Ans✓✓✓Alkene Hydrolysis
Steps: pi bond "grabs" hydrogen, carbocation intermediate, reacts with
water, deprotenation of water to become an alcohol
Product: racemic mixture of alcohol on previously double bonded
carbon with more stable carbocation intermediate
Reactants: Compound with leaving group that will create anything but a
primary carbocation and weakly basic nucleophile in polarizable solvent
Ans✓✓✓Sn1 Rxn (Could be Sn1 or E1, will be told which)
Steps: Leaving group leaves, nucleophile "attacks" carbocation
intermediate
Product: Racemic mixture with nucleophile at same center as leaving
group
Reactants: Compound with leaving group that will create anything but a
primary carbocation and weakly basic nucleophile in polarizable solvent
Ans✓✓✓E1 Rxn (Could be Sn1 or E1, will be told which)
, Steps: Leaving group leaves, base deprotenates an alpha proton, forming
double bond with carbocation to neutralize
Products: Possibly many different alkenes, major product is most
substituted alkene.
Reactants: Compound with leaving group that would create either a
tertiary or secondary carbocation and strongly basic nucleophile
Ans✓✓✓E2 Rxn
Steps: Base deprotenates antiperiplanar hydrogen (180 degrees) on
carbon adjacent to stereocenter with leaving group, forming a double
bond and forcing departure of leaving group.
Product: Alkenes oriented so that any hydrogen and the leaving group
were antiperiplanar before deprotenation. Z alkenes are major products.
Reactants: Compound with leaving group that would create either a
primary or secondary carbocation and very good nucleophile
Ans✓✓✓Sn2 Rxn
Steps: Nucleophile attacks carbon stereochemically opposite from
leaving group, forcing leaving group to depart.
Product: Molecule with nucleophile in a stereochemically reversed
position from where the leaving group was.
Reactants: Carboxylic acid and alcohol in acidic conditions
Ans✓✓✓Fischer Esterification
Steps: Protenate double bonded oxygen, allowing alcohol to "attack" and
form tetrahedral intermediate. Protenate to form a leaving group, then
CORRECT DETAILED ANSWERS (VERIFIED ANSWERS)
|ALREADY GRADED A+||BRAND NEW!
reactants: alkene + acid Ans✓✓✓Steps: pi bond "grabs" hydrogen,
carbocation intermediate, reaction with anion
Product: racemic mixture of anion on previously double bonded carbon
with more stable carbocation intermediate
reactants: alkene + water in acid Ans✓✓✓Alkene Hydrolysis
Steps: pi bond "grabs" hydrogen, carbocation intermediate, reacts with
water, deprotenation of water to become an alcohol
Product: racemic mixture of alcohol on previously double bonded
carbon with more stable carbocation intermediate
Reactants: Compound with leaving group that will create anything but a
primary carbocation and weakly basic nucleophile in polarizable solvent
Ans✓✓✓Sn1 Rxn (Could be Sn1 or E1, will be told which)
Steps: Leaving group leaves, nucleophile "attacks" carbocation
intermediate
Product: Racemic mixture with nucleophile at same center as leaving
group
Reactants: Compound with leaving group that will create anything but a
primary carbocation and weakly basic nucleophile in polarizable solvent
Ans✓✓✓E1 Rxn (Could be Sn1 or E1, will be told which)
, Steps: Leaving group leaves, base deprotenates an alpha proton, forming
double bond with carbocation to neutralize
Products: Possibly many different alkenes, major product is most
substituted alkene.
Reactants: Compound with leaving group that would create either a
tertiary or secondary carbocation and strongly basic nucleophile
Ans✓✓✓E2 Rxn
Steps: Base deprotenates antiperiplanar hydrogen (180 degrees) on
carbon adjacent to stereocenter with leaving group, forming a double
bond and forcing departure of leaving group.
Product: Alkenes oriented so that any hydrogen and the leaving group
were antiperiplanar before deprotenation. Z alkenes are major products.
Reactants: Compound with leaving group that would create either a
primary or secondary carbocation and very good nucleophile
Ans✓✓✓Sn2 Rxn
Steps: Nucleophile attacks carbon stereochemically opposite from
leaving group, forcing leaving group to depart.
Product: Molecule with nucleophile in a stereochemically reversed
position from where the leaving group was.
Reactants: Carboxylic acid and alcohol in acidic conditions
Ans✓✓✓Fischer Esterification
Steps: Protenate double bonded oxygen, allowing alcohol to "attack" and
form tetrahedral intermediate. Protenate to form a leaving group, then
