ORGCHEM Flashcards
1
Q
Which of the following describes a triple bond?
A
One sigma bond and two pi bond
2
Q
- Which carbon(s) in the following molecule is (are) sp hybridized?
A
Carbon 4,5
3
Q
- Triethylamine [(CH₃CH₂)₃N] is a molecule in which the nitrogen atom is ______ hybridized and the CNC bond angle is ______.
A
Sp3 < 109.5 degree
4
Q
- Which of the following statements about ethene, C₂H₄, is incorrect?
A
The H-C-H bond angles are approximately 109.5°.
5
Q
- Which of the following is the strongest acid?
A
CH3CH2OH
6
Q
- Alcohols, phenols, and carboxylic acids all contain an OH group. Which are the strongest acids? Which are the weakest acids?
A
carboxylic acid – strongest, phenol – weaker, alcohol – weakest
7
Q
- Which is the correct order of decreasing acidity of alkanes, alkenes, and alkynes?
A
alkyne > alkene > alkane
8
Q
- Explain the differences in structure between a saturated hydrocarbon and an unsaturated hydrocarbon.
A
A saturated hydrocarbons contains only carbon-carbon single bonds,
while an unsaturated hydrocarbon contains one or more carbon-carbon
double or triple bonds
9
Q
- Biochemical compounds are either hydrophilic, hydrophobic, or amphipathic. Classify the following compounds: glucose, stearic acid, soaps, fatty acids.
A
10
Q
- Which of the following best explains the relative stabilities of the eclipsed and staggered forms of ethane?
A
11
Q
- Which of the following information is the staggered information for rotation about the C₁-C₂ bond in the following structure?
A
12
Q
- Which of the following correctly ranks the cycloalkanes in order of increasing ring strain per methylene?
A
13
Q
- A hydrocarbon, C₅H₁₂, was allowed to react with bromine in the presence of light. Only one monobromo product, C₅H₁₁Br, was formed. What is the structure of the hydrocarbon?
A
14
Q
- Determine whether TRUE or FALSE about the constitutional isomer.
A
15
Q
- Which of the following compounds can exist as geometric isomers?
A
16
Q
- Which of the following is the most stable alkene?
A
17
Q
- Determine the double bond stereochemistry (E or Z) for the following molecules.
A
18
Q
- Which of the following compounds is never chiral?
A
19
Q
- A and B are stereoisomers. They are nonsuperimposable and are mirror images of one another. Which of the following best describes the relationship between A and B?
A
20
Q
- Which of the following physical properties differ for each of a pair of enantiomers?
A
21
Q
- How many stereoisomers exist with the following basic connectivity?
A
22
Q
- How many stereoisomers exist with the following basic connectivity?
A
23
Q
- Determine the relationship between the two molecules shown.
A
24
Q
- Which of the following may be separated by ordinary physical methods?
A
25
29. R-2-pentanol and S-2-pentanol are different with respect to their:
26
30. Which of the following is/are optically inactive?
27
31. A nucleophile acts as a ______ when it reacts with an electrophile.
28
32. Which of the following is not a nucleophile?
29
33. Which of the following are the substitution products of the reaction shown below?
30
34. Which of the following statements is (are) true about an Sₙ2 reaction?
31
35. Rank each of the following halides in order of increasing reactivity in an Sₙ2 displacement reaction.
32
36. Which of the following Sₙ2 reactions is the slowest?
33
37. Which of the following statements about an Sₙ1 mechanism is (are) true?
34
38. Which of the following are the elimination products of the reaction shown below?
35
39. What is the product of the following reaction?
36
40. Which of the alkyl chlorides listed below undergoes dehydrohalogenation in the presence of a strong base to give 2-pentene as the only alkene product?
37
41. What is the major organic product of the following reaction?
38
42. Which of the following halides is least reactive in an E2 reaction with sodium methoxide?
39
43. Predict the two most likely mechanisms for the reaction of 2-iodohexane with sodium ethoxide.
40
44. Dehydrohalogenation of 2-bromobutane in the presence of a strong base proceeds via which of the following mechanistic pathways?
41
45. Which of the following is least likely to be found in the product mixture which results when 2-iodopentane reacts with sodium ethoxide in ethanol?
42
46. Draw the condensed and skeletal structures of diethyl ether which is used by most doctors and hospitals as an anesthetic during operations.
43
47. Williamson synthesis is a procedure for the production of:
44
48. What is the IUPAC name for the following structure?
45
49. Give the IUPAC name for the following structure.
46
50. Which of the following statements is NOT TRUE?
47
51. The Lucas test is used to determine the types of:
48
52. When an alcohol is dehydrated it forms:
49
53. Which of the following alcohols dehydrates with the fastest rate?
50
54. Rank the following alcohols in decreasing order of relative ease of dehydration.
51
55. Which of the following reagents can be used to oxidize 1° alcohols to aldehydes?
52
56. Secondary alcohol when undergoes oxidation forms:
53
57. The alkene formed is the one that is more alkyl substituted.
54
58. What is the IUPAC name for the following compound?
55
59. What is the IUPAC name for the following compound?
56
60. What is the major product from the acid-catalyzed hydration of 2-methyl-2-pentene?
57
61. Isobutyl alcohol can be produced from isobutene through what reaction?
58
62. A reaction sequence used to achieve anti-Markovnikov hydration of an alkene; initiated by concerted syn addition of borane, followed by oxidation with basic hydrogen peroxide.
59
63. If we add Cl₂ to 1-butene, what is the product?
60
64. What is the product of the following reaction?
61
65. The ozonolysis product/s obtained from all the unbranched and unsymmetrical isomers of heptene is/are:
62
66. Ozonolysis (O₃ in CH₂Cl₂) of compound A under reducing conditions (Zn / acetic acid) gives formaldehyde, 2-butanone, and compound B. Catalytic hydrogenation (H₂/Pd) of A gives 2,7-dimethylnonane. What is a possible structure for compound A?
63
67. Which of the following reagents will not yield an alcohol from an alkene?
64
68. What is the IUPAC name for the following alkyne?
65
69. Which of the following compounds is the major product when 1-hexyne is treated with excess HBr?
66
70. Hydration of alkynes yields:
67
71. What are the two possible tautomers for the following ketone?
68
72. Which of the following is the final and major product of this reaction?
69
73. The reagent needed to convert 2-butyne to cis-2-butene is:
70
74. Which of the following is aromatic?
71
75. What is the proper name of the compound below?
72
76. What is the name of the following compound?
73
77. Which of the following is the electrophile that attacks the aromatic ring during nitration?
74
78. What is the major organic product of the reaction between benzene and isobutyl chloride in the presence of AlCl₃?
75
79. In electrophilic aromatic substitution reactions a chlorine substituent:
76
80. Which of the following substrates is an electron withdrawing group overall?
77
81. Which of the following compounds reacts most rapidly with HNO₃/H₂SO₄?
78
82. What is the major product of the following reaction?
79
83. Starting with benzene, the best method for preparing p-nitrobenzoic acid is:
80
84. Synthesize para-chlorobenzoic acid from benzene as the raw material.
81
85. Hydrolysis of an ester leads to two compounds. Which of the following pairs of compounds is formed from such a hydrolysis?
82
86. What compound can be used to convert alcohol or a phenol into an ester?
83
87. An acid chloride forms an ester by which of the following reactions?
84
88. What organic product is formed when C₆H₅CH₂COOH is treated with CH₃OH + H₂SO₄ (catalyst)?
85
89. What is a proper name for the following ester?
86
90. An unknown ester, C₆H₁₂O₂, was hydrolyzed with water and acid to produce acid X and alcohol Y. Oxidation of Y with chronic acid produced X. What was the structure of the ester?
87
91. An unknown ester was hydrolyzed with water and acid to produce an acid X and alcohol Y. Oxidation of the alcohol with hot KMnO₄ yielded acid X. Oxidation of the alcohol produces acetaldehyde. Name the ester.
88
92. Consider the three isomeric alkanes n-hexane, 2,3-dimethylbutane, and 2-methylpentane. Which of the following correctly lists these compounds in order of increasing boiling point?
89
93. Which of the following alkanes will have the lowest boiling point?
90
94. Pentane has three structural isomers: (A) n-pentane, (B) neopentane, and (C) isopentane. Arrange these isomers in increasing boiling point.
91
95. Predict which of the following compounds will have a lower boiling point than 1-butanal.
92
96. In the study of fats and lipids, determine which of the two triglycerides has a higher melting point, substance A containing only lauric acid and glycerol, or substance B containing only stearic acid and glycerol?
93
97. Which of the following is the most soluble in H₂O?
94
98. The following are correctly named except:
95
99. Taurine, a Beta amino acid belongs to the acidic group of:
96
100. What type of polymer is used for bulletproof vests?
97
101. The person's senses of smell and taste depend on specific biochemical receptors present in a person's nose and mouth. In 2004, a Nobel prize was given to the researchers who established this fact and identified the type of organic compound associated with the sense of smell and taste. The chemical identified was:
98
102. Name the major physiologically active substances that come from: bark of the willow tree, the pituitary gland, the sap of the poppy, and the belladonna plant.
99
103. What is the Nujol Mull in organic chemical reactions?
100
104. What are sigmatropic rearrangements in organic reactions?
