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Organic Chemistry

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1
What is the pKa of H-I
-10
2
What is the pKa of H-Br
-9
3
What is the pKa of H-Cl
-7
4
What is the pKa of Sulfuric Acid (H2SO4)
-3
5
What is the pKa of hydronium (H3O+)
-2
6
What is the pKa of carboxylic acid (R-COOH)
5
7
What is the pKa of H-F
4
8
What is the pKa of R-SH
7-8
9
What is the pKa of R-NH3+
10
10
what is the pKa of -OH
16
11
what is the A-value of a methyl (-CH3)
1.74
12
What is the A-value of an ethyl (-CH2-CH3)
1.79 (Close to methyl due to free bond rotation)
13
What is the A-Value of a propyl group (CH2-CH2-CH3)
2.21
14
What is the A-value of tert-butyl (tBu)
5.5
15
What is the A-Value for -F
0.3
16
What is the A-Value for -Cl and -Br
0.6
17
What is the A-Value for -I
0.5
18
What is the A-Value of -OH and -OMe
0.6
19
What is the A-Value of -SH and -NH2
1.2
20
What is the A-Value of -NH3+
1.8
21
What is the energy of a H-H Eclipsed
1 kcal/mol
22
What is the energy of a H-CH3 eclipsed
1.5 kcal/mol
23
What is the energy of a CH3-CH3 eclipsed
3 kcal/mol
24
What is the energy of a CH3-CH3 gauche
0.9 kcal/mol
25
What is the strain energy of cyclopropane
27 kcal/mol (6 from torsional/21 from angle strain)
26
What is the strain energy of cyclobutane
26 kcal/mol
27
What is the strain energy of cyclopentane
6 kcal/mol (All Torsional Strain)
28
What is the strain energy of cyclohexane
0 kcal/mol (chair conformation)
29
What is the strain energy of cycloheptane
6 kcal/mol
30
What is the strain energy of cyclooctane
9 kcal/mol
31
What is the equation for energy
G = -RTln(K)
32
Is SR(-) a great, good, or okay nucleophile
Great
33
is SH(-) a great, good, or okay nucleophile
Great
34
Is cyanide ( CN(-) ) a great, good, or okay nucleophile
Great
35
Is I (-) a great, good, or okay nucleophile
Great
36
Is PR3 a great, good, or okay nucleophile
Great
37
Is NR2(-) a great, good, or okay nucleophile
Great
38
Is N3(-) a great, good, or okay nucleophile
Good
39
Is OH(-) a great, good, or okay nucleophile
Good
40
Is OR(-) a great, good, or okay nucleophile
Good
41
Is Br(-) a great, good, or okay nucleophile
Good
42
Is NR3 a great, good, or okay nucleophile
Good
43
is R-SH a great, good, or okay nucleophile
Good
44
Is R-S-R a great, good, or okay nucleophile
Good
45
is an alkyne ion(-) a great, good, or okay nucleophile
Good
46
the Cl(-) a great, good, or okay nucleophile
Okay
47
is F(-) a great, good, or okay nucleophile
Okay
48
Is R-COO(-) a great, good, or okay nucleophile
Okay
49
is H2O a great, good, or okay nucleophile
Okay
50
Is R-OH a great, good, or okay nucleophile
Okay
51
Is R-I a Good or Poor leaving group
Good
52
Is R-Br a Good or Poor leaving group
Good
53
Is R-Cl a Good or Poor leaving group
Good
54
Is R-HSO3 a Good or Poor leaving group
Good
55
Is R-OH2 (+) a Good or Poor leaving group
Good
56
Is R-F a Good or Poor leaving group
Poor
57
Is R-SH a Good or Poor leaving group
Poor
58
is R-CN a Good or Poor leaving group
Poor
59
is R-OH a Good or Poor leaving group
Poor
60
What reaction would take place on a Methyl carbon
Sn2
61
What reaction would take place on a primary carbon with a strong basic nucleophile
E2
62
What Reaction would take place on a secondary carbon with a strong basic nucleophile with H-antiperiplanar
E2 major
63
What reaction would take place on a secondary carbon with a strong nonbasic nucleophile
Sn2 major
64
What reaction would take place on a secondary carbon with a weak nucleophile
Sn1 and E1
65
What reaction would take place on a tertiary carbon with a very basic nucleophile and an H-antiperiplanar
E1
66
What reaction would take place on a tertiary carbon with a nonbasic nucleophile
Sn1 and E1
67
if pH < pKa are there more protonated or deprotonated species
Protonated
68
if pH > pKa are there more protonated or deprotonated species
Deprotonated
69
What mechanism can be used to perform H-X on a unstable carbocation
Hydroboration and Radical Initiation
70
What Mechanism can be used to add a halide to an alcohol while flipping stereochemistry
P-X3 addition (X=Halide)
71
What mechanism can be used to add a halide to an alcohol while retaining stereochemistry
SOCl2 addition
72
What mechanism can create a ketone from an alcohol
CrO3 and Pyridine
73
What mechanism can create a carboxylic acid from an alcohol
Cr2O7, H2SO4, and H20
74
What mechanism can create an alcohol from a carbonyl
NaBH4 (aldehyde) or LiAlH4 (ketone)
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