DAT Organic Chemistry Study Review
Practice Test.
Enantiomer - CORRECT ANSWER Non-superposable mirror images
Diastereomer - CORRECT ANSWER Non-mirror images with same chemical formula
Meso Compound - CORRECT ANSWER Achiral but has stereocenters
Why are axial conformations of large substituents less stable than equatorial conformations? - CORRECT
ANSWER 1, 3 diaxial interactions
What rings have more ring strain? - CORRECT ANSWER Smaller rings, but not cyclohexane
General formula for maximum possible number of isomers? - CORRECT ANSWER 2^n where n equals the
number of stereocenters on a compound
How to get Keq when given pKa - CORRECT ANSWER Keq = [H3O+][A-]/[HA][H2O]
How to rank bases - CORRECT ANSWER C - charge
A - atom
Charge on larger atom
Charge in more electronegative atom
R - resonance
D - dipole induction
O - orbital (percent s character)
Lewis Acid - CORRECT ANSWER Electron pair acceptor
,Lewis Base - CORRECT ANSWER Electron paid donor
Bronsted-Lowry Acid - CORRECT ANSWER Proton donor
Bronsted-Lowry Base - CORRECT ANSWER Proton acceptor
Index of Hydrogen Deficiency - CORRECT ANSWER [(2C + 2 + N)-X-H]/2
Vinyl Group - CORRECT ANSWER --CH2CH=CH2
Allyl Group - CORRECT ANSWER --CHCH2CH=CH2
Alkene + Acid in Water - CORRECT ANSWER 1. Formation of carbocation
2. Rearrangement if possible
3. Addition of H2O
4. Deprotonation
Oxomercuration-Demercuration Reactants - CORRECT ANSWER Alkene + Hg(OAc)2, H2O
Reduction by Sodium Borohydride
Oxomercuration-Demercuration Addition - CORRECT ANSWER Markovnikov Addition of -OR or -OH to
more substituted carbon, HgOAc to less substituted carbon
Hydroboration Reactants - CORRECT ANSWER Alkene+BH3, THF in EtOH followed by H2O2, NaOH
Hydroboration Addition - CORRECT ANSWER Antimarkovnikov -OH adds to less substituted carbon
Alkene+HBr in ROOR - CORRECT ANSWER Antimarkovnikov addition of -Br
, Alkene + Br2 in H2O - CORRECT ANSWER -OH adds to more substituted carbon, -Br to less substituted
carbon
Antiaddition
Alkene + Br2 in inert solvent like CCl4 - CORRECT ANSWER Antiaddition of both -Br, cyclic bromonium
intermediate
Alkene + OsO4 followed by NaHSO3 and H2O - CORRECT ANSWER Oxidation reaction; syn addition of
two -OH
Alkene+O3 followed by (CH3)2S - CORRECT ANSWER Oxidative Cleavage to aldehyde or ketone
Alkene+KMnO4, hot and concentrated followed by Acidic Workup - CORRECT ANSWER Oxidative
Cleavage to aldehyde or ketone
Alkene+H2/Pd or Pt - CORRECT ANSWER Syn addition of 2 H into alkane
Alkene+Peracid in MCPBA - CORRECT ANSWER Antiaddition of 2 -OH
Peracid is RCO3H
What is the only stable cycloalkyne at room temperature? - CORRECT ANSWER Cyclononyne
Synthesis of an Alkyne - CORRECT ANSWER Adjacent Dibromoalkane + NaNH2 in DMSO
Terminal Alkyne+NaNH2 followed by primary bromoalkane - CORRECT ANSWER 1. Deprotonation of
Alkyne (good Nu)
2. Backside attack by Nu, Br leaves
Practice Test.
Enantiomer - CORRECT ANSWER Non-superposable mirror images
Diastereomer - CORRECT ANSWER Non-mirror images with same chemical formula
Meso Compound - CORRECT ANSWER Achiral but has stereocenters
Why are axial conformations of large substituents less stable than equatorial conformations? - CORRECT
ANSWER 1, 3 diaxial interactions
What rings have more ring strain? - CORRECT ANSWER Smaller rings, but not cyclohexane
General formula for maximum possible number of isomers? - CORRECT ANSWER 2^n where n equals the
number of stereocenters on a compound
How to get Keq when given pKa - CORRECT ANSWER Keq = [H3O+][A-]/[HA][H2O]
How to rank bases - CORRECT ANSWER C - charge
A - atom
Charge on larger atom
Charge in more electronegative atom
R - resonance
D - dipole induction
O - orbital (percent s character)
Lewis Acid - CORRECT ANSWER Electron pair acceptor
,Lewis Base - CORRECT ANSWER Electron paid donor
Bronsted-Lowry Acid - CORRECT ANSWER Proton donor
Bronsted-Lowry Base - CORRECT ANSWER Proton acceptor
Index of Hydrogen Deficiency - CORRECT ANSWER [(2C + 2 + N)-X-H]/2
Vinyl Group - CORRECT ANSWER --CH2CH=CH2
Allyl Group - CORRECT ANSWER --CHCH2CH=CH2
Alkene + Acid in Water - CORRECT ANSWER 1. Formation of carbocation
2. Rearrangement if possible
3. Addition of H2O
4. Deprotonation
Oxomercuration-Demercuration Reactants - CORRECT ANSWER Alkene + Hg(OAc)2, H2O
Reduction by Sodium Borohydride
Oxomercuration-Demercuration Addition - CORRECT ANSWER Markovnikov Addition of -OR or -OH to
more substituted carbon, HgOAc to less substituted carbon
Hydroboration Reactants - CORRECT ANSWER Alkene+BH3, THF in EtOH followed by H2O2, NaOH
Hydroboration Addition - CORRECT ANSWER Antimarkovnikov -OH adds to less substituted carbon
Alkene+HBr in ROOR - CORRECT ANSWER Antimarkovnikov addition of -Br
, Alkene + Br2 in H2O - CORRECT ANSWER -OH adds to more substituted carbon, -Br to less substituted
carbon
Antiaddition
Alkene + Br2 in inert solvent like CCl4 - CORRECT ANSWER Antiaddition of both -Br, cyclic bromonium
intermediate
Alkene + OsO4 followed by NaHSO3 and H2O - CORRECT ANSWER Oxidation reaction; syn addition of
two -OH
Alkene+O3 followed by (CH3)2S - CORRECT ANSWER Oxidative Cleavage to aldehyde or ketone
Alkene+KMnO4, hot and concentrated followed by Acidic Workup - CORRECT ANSWER Oxidative
Cleavage to aldehyde or ketone
Alkene+H2/Pd or Pt - CORRECT ANSWER Syn addition of 2 H into alkane
Alkene+Peracid in MCPBA - CORRECT ANSWER Antiaddition of 2 -OH
Peracid is RCO3H
What is the only stable cycloalkyne at room temperature? - CORRECT ANSWER Cyclononyne
Synthesis of an Alkyne - CORRECT ANSWER Adjacent Dibromoalkane + NaNH2 in DMSO
Terminal Alkyne+NaNH2 followed by primary bromoalkane - CORRECT ANSWER 1. Deprotonation of
Alkyne (good Nu)
2. Backside attack by Nu, Br leaves
