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