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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 sub...

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  • August 15, 2024
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  • 2024/2025
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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

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