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