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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. Oxidize to -CHO
Nucleophilic Aromiatic Substitution
Pyridine
SN1
Benzene + CO + HCl (w/ AlCl3)
2. Reduces one bond of benzene ring
Birch reduction
Oxime
Saytzeff Product
Thioacetal
3. Bound to same atom
Halohydrin + Base
Geometrical isomer
Geminal
Benzene + CO + HCl (w/ AlCl3)
4. Differ in rotation about sigma bonds
Conformational Isomer
Thioacetal
Hofmann Product
1 -2 Dihalide + Zn
5. Donate electrons to aromatic ring
Addition of Alkali Metal to alcohol
O-P Directors
SN1
Nucleophilic Aromiatic Substitution
6. Thionyl chloride
SOCl2
Constitutional Isomer
1 -2 Dihalide + Zn
Hofmann Product
7. Highly reactive carbonyl
Oxime
Acyl Chloride
RSH + KMnO4
Benzyl hydrogenolysis
8. Differ in fixed geometrical arrangement of atoms
Stereoisomers
Peroxyacid
1 -2 Dihalide + Zn
Clemmenson reaction
9. Split an alkene into 2 carbonyls
Enantiomer
Benzyl hydrogenolysis
Ozonolysis
Geometrical isomer
10. Chiral - with superimposable mirror image
Geometrical isomer
Benzene + CO + HCl (w/ AlCl3)
Thioacetal
Meso compound
11. Tertiary carbon center; racemic
SN2
Conformational Isomer
SN1
KMnO4
12. CH2-
C=O + Zn - Hg / HCl
SN1
Addition of Alkali Metal to alcohol
KMnO4
13. Reacts with alkene to form oxirane
Methoxy group
Hg(OAc)2
E1 Elimination
Peroxyacid
14. Cyclic ether
Nucleophilic Addition
1 -3-dithiane + BuLi / R-OH
Oxirane
NBS
15. Bound to adjacent atoms
Vicinal
Clemmenson reaction
SN2
SOCl2
16. R-SO3H
KMnO4
Hofmann Product
Conformational Isomer
RSH + KMnO4
17. Aldehyde / ketone synthesis
Acyl Chloride
1 -3-dithiane + BuLi / R-OH
Forms cyclopropane ring from alkene
Peroxyacid
18. Oxirane ring opening
Nucleophilic Addition
Nucleophilic Aromiatic Substitution
Anti-orientation
Geometrical isomer
19. Less hindered carbon center; chiral inversion
SN2
RSH + KMnO4
Diels-Alder
1 -3-dithiane + BuLi / R-OH
20. Tertiary carbocation formed; relieved by deprotonation
Hg(OAc)2
E1 Elimination
Birch reduction
KMnO4
21. Ph-NH2
Aniline
Clemmenson reaction
Geminal
Hofmann Product
22. Cis/trans Isomers
Conformational Isomer
E1 Elimination
HBr or HI cleavage
Geometrical isomer
23. 2 Sulfide linkages in place of aldehyde
RSH + KMnO4
O-P Directors
Thioacetal
1 -2 Dihalide + Zn
24. Allylic Substitution
Diels-Alder
NBS
1 -3 Dihalide + Zn
SN2
25. Anti-alignment required
Oxidizes amine groups
Nucleophilic Addition
E2 Elimination
SN2
26. Cycloformation
Birch reduction
Geminal
1 -3 Dihalide + Zn
Solvomercuration-demercuration
27. R2C=N-OH
Diazotization
Diels-Alder
Oxime
Conformational Isomer
28. Alcohol closes ring to form oxirane
E2 Elimination
KMnO4
Hg(OAc)2
Halohydrin + Base
29. Elimination to form alkene
E1 Elimination
Birch reduction
1 -2 Dihalide + Zn
Forms cyclopropane ring from alkene
30. Differ in position of atoms
Thioacetal
Constitutional Isomer
Saytzeff Product
Anti-orientation
31. Oxidize to -COOH
1 -2 Dihalide + Zn
Hg(OAc)2
Chromic Acid
Oxirane
32. Non-superimposable mirror image
O-P Directors
Oxime
HBr or HI cleavage
Enantiomer
33. Replaces thioacetal/ketal with carbonyl
Constitutional Isomer
NBS
H+ - HgCl2 - H2O
Benzyl hydrogenolysis
34. R-NH2 + NaNO2/HCl --> R-N=N+ Cl-
Geminal
Nucleophilic Aromiatic Substitution
Benzene + CO + HCl (w/ AlCl3)
Diazotization
35. Formation of ethoxide
Addition of Alkali Metal to alcohol
Oxime
Peroxyacid
SN2
36. Less substituted elimination; sterically hindered
H+ - HgCl2 - H2O
Birch reduction
Hofmann Product
Stereoisomers
37. More substituted elimination; more stable
Nitrile + H2O/H+
Saytzeff Product
Acyl Chloride
Solvomercuration-demercuration
38. Reduces ketone to alkane
Thioacetal
Thioacetal
Clemmenson reaction
Acyl Chloride
39. Formation of salcohol from alkene
Forms cyclopropane ring from alkene
Hg(OAc)2
RSH + KMnO4
E2 Elimination
40. OCH3
Tosylation
O-P Directors
Nucleophilic Aromiatic Substitution
Methoxy group
41. H2O2
H+ - HgCl2 - H2O
SOCl2
Oxirane
Oxidizes amine groups
42. Ch2I2 - Zn(Cu)
Forms cyclopropane ring from alkene
Stereoisomers
HBr or HI cleavage
Tosylation
43. Best with electron withdrawing group ortho/para to substitution site
Pyridine
1 -3-dithiane + BuLi / R-OH
Oxirane
Nucleophilic Aromiatic Substitution
44. Benzaldehyde
Tosylation
Geminal
Nucleophilic Aromiatic Substitution
Benzene + CO + HCl (w/ AlCl3)
45. Attach tosyl group onto alcohol
Methoxy group
SN2
Thioacetal
Tosylation
46. Nucleophile adds to ketone (forming alcohol)
Nucleophilic Addition
Constitutional Isomer
Oxidizes amine groups
Nitrile + H2O/H+
47. One carbon away from aryl group can be reduced with Pd / H2
E2 Elimination
Benzyl hydrogenolysis
Oxirane
Nucleophilic Aromiatic Substitution
48. Reduces Ar-CH3 to -COOH
Meso compound
KMnO4
Saytzeff Product
Nucleophilic Addition
49. 4-pi system + 2-pi system --> Ring formation
Tosylation
Anti-orientation
Diels-Alder
Hofmann Product
50. Can protect a ketone
Thioacetal
RSH + KMnO4
Aniline
Solvomercuration-demercuration