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