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Test your basic knowledge |
GRE Chemistry Organic
Start Test
Study First
Subjects
:
gre
,
science
,
chemistry
Instructions:
Answer 50 questions in 15 minutes.
If you are not ready to take this test, you can
study here
.
Match each statement with the correct term.
Don't refresh. All questions and answers are randomly picked and ordered every time you load a test.
This is a study tool. The 3 wrong answers for each question are randomly chosen from answers to other questions. So, you might find at times the answers obvious, but you will see it re-enforces your understanding as you take the test each time.
1. Reduces ketone to alkane
Nitrile + H2O/H+
Oxidizes amine groups
HBr or HI cleavage
Clemmenson reaction
2. Elimination to form alkene
Benzene + CO + HCl (w/ AlCl3)
1 -2 Dihalide + Zn
Meso compound
1 -3 Dihalide + Zn
3. Cycloformation
RSH + KMnO4
1 -3 Dihalide + Zn
Thioacetal
Thioacetal
4. R-SO3H
SN2
Chromic Acid
H+ - HgCl2 - H2O
RSH + KMnO4
5. One carbon away from aryl group can be reduced with Pd / H2
Peroxyacid
RSH + KMnO4
Benzyl hydrogenolysis
Oxidizes amine groups
6. Ch2I2 - Zn(Cu)
Benzyl hydrogenolysis
Clemmenson reaction
Nucleophilic Aromiatic Substitution
Forms cyclopropane ring from alkene
7. Reduces Ar-CH3 to -COOH
NBS
KMnO4
Benzyl hydrogenolysis
Oxime
8. H2O2
Oxirane
Oxidizes amine groups
Ozonolysis
Diels-Alder
9. Cyclic ether
Vicinal
KMnO4
SN2
Oxirane
10. Reacts with alkene to form oxirane
Peroxyacid
Nucleophilic Addition
1 -3 Dihalide + Zn
Solvomercuration-demercuration
11. Forms carboxylic acid; releases N
Nucleophilic Addition
Thioacetal
Nitrile + H2O/H+
Forms cyclopropane ring from alkene
12. Differ in position of atoms
Saytzeff Product
Constitutional Isomer
Anti-orientation
SOCl2
13. CH2-
Enantiomer
Oxime
C=O + Zn - Hg / HCl
Nucleophilic Aromiatic Substitution
14. Reduces one bond of benzene ring
E2 Elimination
Birch reduction
Conformational Isomer
Benzene + CO + HCl (w/ AlCl3)
15. Less substituted elimination; sterically hindered
Hofmann Product
C=O + Zn - Hg / HCl
Acyl Chloride
1 -3-dithiane + BuLi / R-OH
16. Ph-NH2
1 -3-dithiane + BuLi / R-OH
Aniline
Geometrical isomer
Forms cyclopropane ring from alkene
17. Split an alkene into 2 carbonyls
1 -2 Dihalide + Zn
Anti-orientation
Ozonolysis
Tosylation
18. More substituted elimination; more stable
NBS
1 -2 Dihalide + Zn
Saytzeff Product
SN1
19. Formation of salcohol from alkene
Hg(OAc)2
Halohydrin + Base
Oxime
Nitrile + H2O/H+
20. Attach tosyl group onto alcohol
Tosylation
Ozonolysis
HBr or HI cleavage
Pyridine
21. Anti-alignment required
Enantiomer
E2 Elimination
Ozonolysis
Thioacetal
22. Replaces thioacetal/ketal with carbonyl
Peroxyacid
NBS
Enantiomer
H+ - HgCl2 - H2O
23. Benzaldehyde
O-P Directors
Hg(OAc)2
Benzene + CO + HCl (w/ AlCl3)
Diels-Alder
24. Thionyl chloride
SOCl2
Hg(OAc)2
Birch reduction
Geometrical isomer
25. Alcohol closes ring to form oxirane
RSH + KMnO4
Meso compound
Halohydrin + Base
Benzene + CO + HCl (w/ AlCl3)
26. Non-superimposable mirror image
NBS
C=O + Zn - Hg / HCl
Pyridine
Enantiomer
27. Aldehyde / ketone synthesis
Oxidizes amine groups
SOCl2
Ozonolysis
1 -3-dithiane + BuLi / R-OH
28. Formation of ethoxide
C=O + Zn - Hg / HCl
Addition of Alkali Metal to alcohol
1 -3-dithiane + BuLi / R-OH
H+ - HgCl2 - H2O
29. Splits an ether into alkyl halides
Diazotization
Benzene + CO + HCl (w/ AlCl3)
HBr or HI cleavage
C=O + Zn - Hg / HCl
30. Tertiary carbon center; racemic
Ozonolysis
1 -3 Dihalide + Zn
Benzene + CO + HCl (w/ AlCl3)
SN1
31. Allylic Substitution
Thioacetal
NBS
Addition of Alkali Metal to alcohol
Diazotization
32. Best with electron withdrawing group ortho/para to substitution site
Meso compound
HBr or HI cleavage
SN1
Nucleophilic Aromiatic Substitution
33. Chiral - with superimposable mirror image
Hg(OAc)2
Nitrile + H2O/H+
Meso compound
RSH + KMnO4
34. Donate electrons to aromatic ring
Tosylation
O-P Directors
Anti-orientation
SN1
35. Less hindered carbon center; chiral inversion
SN2
1 -2 Dihalide + Zn
Halohydrin + Base
NBS
36. Bound to same atom
Forms cyclopropane ring from alkene
KMnO4
NBS
Geminal
37. Differ in fixed geometrical arrangement of atoms
Meso compound
Stereoisomers
Nitrile + H2O/H+
E2 Elimination
38. R-NH2 + NaNO2/HCl --> R-N=N+ Cl-
Diazotization
KMnO4
Solvomercuration-demercuration
NBS
39. Uses Hg(OAc)2 + R'OH; forms ether from alkene
Solvomercuration-demercuration
RSH + KMnO4
Oxirane
Nucleophilic Addition
40. 4-pi system + 2-pi system --> Ring formation
Diels-Alder
Conformational Isomer
Nucleophilic Aromiatic Substitution
Stereoisomers
41. R2C=N-OH
Oxime
Ozonolysis
NBS
Clemmenson reaction
42. Oxidize to -CHO
Pyridine
E2 Elimination
Benzene + CO + HCl (w/ AlCl3)
Oxidizes amine groups
43. Oxirane ring opening
NBS
Anti-orientation
Conformational Isomer
Aniline
44. Oxidize to -COOH
Chromic Acid
Peroxyacid
Birch reduction
1 -3 Dihalide + Zn
45. Highly reactive carbonyl
Birch reduction
Acyl Chloride
Clemmenson reaction
1 -3 Dihalide + Zn
46. Differ in rotation about sigma bonds
Conformational Isomer
Acyl Chloride
E2 Elimination
SN2
47. Nucleophile adds to ketone (forming alcohol)
Ozonolysis
Oxirane
Clemmenson reaction
Nucleophilic Addition
48. Bound to adjacent atoms
Peroxyacid
E2 Elimination
1 -3 Dihalide + Zn
Vicinal
49. Can protect a ketone
Geminal
Thioacetal
Enantiomer
Geometrical isomer
50. Cis/trans Isomers
1 -3 Dihalide + Zn
Peroxyacid
Addition of Alkali Metal to alcohol
Geometrical isomer