Final Flashcards
(102 cards)
1
Q
Same side of double bond
A
Z
2
Q
Opposite side of double bond
A
E
3
Q
RCOOR
A
Ester
4
Q
ROR
A
Ether
5
Q
OCNH2
A
Amide
6
Q
Formal charge
A
(# of valence e-) - (lone pairs + 1/2 bonds)
7
Q
Aromaticity
A
4n + 2
Conjugated
+ and - count
8
Q
What is the hybridization of the orbital containing the unshared e- on the nitrogen atom in pyridine?
A
sp2
9
Q
Benzene hybridization
A
sp2
10
Q
R-CH2
Carbon hybridization
A
sp3
11
Q
Ketone carbon (dbl bonded to the O) hybridization
A
sp2
12
Q
R-OH
O hybridization
A
sp3
13
Q
Most stable heat of combustion
A
Highest kJ/CH2
14
Q
Most stable carbocations
A
R-CH
+ on the carbon closest to the benzene ring
15
Q
Near pH 7
A
NH3+ and O-
16
Q
Strongest base
A
R–CH2NH2
17
Q
Carboxylate strongest base
A
CH2CH2CH2COO-
18
Q
Strongest to weakest acid
A
OH+>NH3+>OH>NH2
19
Q
Most acidic to least acidic
A
1 ketone and 1 COOCH > ketone> COOCH > CH3CH3
20
Q
Greater acidity of p-nitro phenol
A
- on both NO2 O’s and + on N
21
Q
Most acidic proton
A
OH
22
Q
Smallest pKa
A
Least acidic H
23
Q
Strongest to weakest acid
A
SOOH >SOOH > COOH
24
Q
R-CH2CH3 –H2O/H+–>
A
Add OH to the same carbon CH2CH3 is on
25
R--CH3 --1.B2H6/2.H2O2, NaOH-->
CH3 up and OH is added one carbon down from CH3 pointing down
26
Hg(OAc)2, H2O followed by NaBH4
Adds an OH where a double bond was
27
HCl
Adds Cl to most substituted carbon
28
Nucleophile that adds an OH to a double bond
H2O
29
H2O, H2SO4/HgSO4
Creates a ketone on the carbon that had double bonds closest to the ring
30
Propene to Propanol
B2H6, followed by H2O2, NaOH
31
Adding Br2 to (E)-3-hexene
One meso compound
32
R-CH3 --1.Hg(OAC)2, H2O/2. NaBH4-->
OH added to same carbon as CH3
33
Furan ---Br2/CH3OH-->
Adds OCH3 next to O and Br next to OCH3
34
1. R-BH/2. H2O2, NaOH
Adds aldehyde at the very end of the double bond
35
R-C (triple bonded)CH --> R-Ketone
H20,H2SO4/ HgSO4
36
A compound with two double bonds + HCl + CL2
Cl on each of the double bonds
37
R-CH3 --HCl-->
Cl adds to the same carbon as CH3
38
Double bond in a ring ---> Epoxide
RCO3H
39
Butene ---CHCl3/(CH3)3COK-->
Dimethyl cyclopropane with the CH3's pointing it two different directions and 2 Cl's at the top
40
R-CH3 ---Br2/H2O-->
CH3 and OH on one carbon (CH3 up OH down) and Br (up) one carbon down
41
Different compounds with the same molecular formula
Isomers
42
Isomers that have a different atom connectivity
Constitutional Isomers
43
Isomers that have the same connectivity but differ in the arrangement of their atoms in space
Stereoisomers
44
Stereoisomers that are nonsuperimposible mirror reflections of each other
Enatiomers
45
Stereoisomers that are not mirror images of each other
Diastereomers (two molecules switched)
46
A mixture of two enantiomers in equal concetrations
Racemic
| Optically inactive
47
compound is "superposable" on its mirror image (not to be confused with superimposable, as any two objects can be superimposed over one another regardless of whether they are the same.
Meso
48
Nucleophile attacks carbon bound to electronegative atom
Substitution Reactions
49
Nucleophile can be a base and react with acidic protons of alkyl substrates
Elimination
50
! step
Bimolecular
Rate is 1st order
Inversion occrus
Sn2
51
2 steps
Ionization of alkyl substrate then reacts with nucleophile
Unimolecular
sp2 tetrahedral
Sn1
52
NuH + X-
E2
53
compound + NuH or compound + X-
E1
54
Primary
Strong (like OH-) or Weak base (like Cl-)
Good Nucleophile
Sn2
55
Primary
Strong Base (like OH-)
Non-nucleophilic bases
E2
56
Secondary
| Strong (like OH-) or Weak Base (like Cl-)
Sn2
57
```
Secondary
Poor Nucleophile (like H2O or HOR)
```
Sn1/E1 (slow), in polar, protic solvents
58
```
Tertiary
Strong base (like OH-)
```
E2
59
```
Tertiary
Weak base (like Cl-)
```
Sn1/E1 in polar, protic solvents
60
```
Tertiary
Poor Nucleophile (like H2O or ROH)
```
Sn1/E1 in polar, protic solvents
61
O-H and N-H Frequency
3400
62
C-H (sp3)
3000-2850
63
C-H (sp2)
3000-3100
64
C-H (sp)
3300
65
C (triple bond) C and C (triple bond) N
2100
66
C=O
1700
67
C=C, aromatic C-C
1600
68
Aromatic C-C
1500
69
atom with 4 bonds
sp3
70
atom with 3 bonds
sp2
71
atom with 2 bonds
sp
72
atom with 1 bond
s
73
Carbocation stability
Tertiary > Secondary > Primary > Vinyl
74
Ranking acids
EN > Distance from EN molecule> No EN molecule
75
pH of 12
Deprotonates
76
Acidity
HI>HBR, HCl, HF
77
Larger atom
More nucleophilic
78
Allylic and Benzylic halides undergo
Sn2 faster
79
If catalyzed by acid, and nuc = primary amine
C-N imine
80
If catalyzed by acid and nuc = secondary amine
C=C enamine
81
Strong basic nuc like grignard or metal halides
1,2 addition
82
Weak basic nut like R2CuLi
1,4 addition
83
Stability of organic radicals
Allylic/Benzylic > tertiary alkyl > secondary alkyl > primary alkyl > methyl > vinylic/aryl
84
Initiation
Generates radicals
| Step 1
85
Propagation
Radical reacts with stable molecule to produce a new radical
| Step 2
86
Termination
Destroys radicals and stops the reaction
| Step 3
87
Hydrogen atom count decreased
Oxidation
88
Hydrogen atom count increased
Reduction
89
Oxidizing agents
CrO3, K2Cr2O7, K2CrO4, KMnO4
Chromium used under acidic conditions
Potassium Permanganate used under basic conditions
90
Oxidize only to aldehyde state
CrO3-2 pyridine, PCC, PDC
91
Cleavage
HIO4 by ozone
92
CH3MgBr
Oxidizes C=O and turns OCH3 into OH
93
Hg(OAc)2, NaBH4/NaOH
Combines two molecules removing the double bond and the H from the OH
94
NH3/H2,Pt
Oxidizes C=O and adds NH2
95
KOH, CH2=CHCH2Br, H20 NaOH/heat
breaks apart two fused rings leaving only one c=c behind and adds NH2
96
SoCl2/heat, NH3, Br2/NaOH
reduces ketone and replaces OH with NH2
97
R-C(OH)HCH3
yellow precipitate
98
NO2
meta directing
99
Most to least reactive with NH3
Cl > anhydride > ester >amide
100
SoCl2
Turns carboxylic acid to anhydride
101
-OD/D2O
replaces only the alpha hydrogens
102
NaCN
1,4 Addition
