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