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Organic Chemistry > Final > Flashcards

Final Flashcards

1
Q

Same side of double bond

A

Z

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2
Q

Opposite side of double bond

A

E

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3
Q

RCOOR

A

Ester

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4
Q

ROR

A

Ether

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5
Q

OCNH2

A

Amide

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6
Q

Formal charge

A

(# of valence e-) - (lone pairs + 1/2 bonds)

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7
Q

Aromaticity

A

4n + 2
Conjugated
+ and - count

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8
Q

What is the hybridization of the orbital containing the unshared e- on the nitrogen atom in pyridine?

A

sp2

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9
Q

Benzene hybridization

A

sp2

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10
Q

R-CH2

Carbon hybridization

A

sp3

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11
Q

Ketone carbon (dbl bonded to the O) hybridization

A

sp2

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12
Q

R-OH

O hybridization

A

sp3

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13
Q

Most stable heat of combustion

A

Highest kJ/CH2

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14
Q

Most stable carbocations

A

R-CH

+ on the carbon closest to the benzene ring

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15
Q

Near pH 7

A

NH3+ and O-

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16
Q

Strongest base

A

R–CH2NH2

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17
Q

Carboxylate strongest base

A

CH2CH2CH2COO-

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18
Q

Strongest to weakest acid

A

OH+>NH3+>OH>NH2

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19
Q

Most acidic to least acidic

A

1 ketone and 1 COOCH > ketone> COOCH > CH3CH3

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20
Q

Greater acidity of p-nitro phenol

A
  • on both NO2 O’s and + on N
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21
Q

Most acidic proton

A

OH

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22
Q

Smallest pKa

A

Least acidic H

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23
Q

Strongest to weakest acid

A

SOOH >SOOH > COOH

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24
Q

R-CH2CH3 –H2O/H+–>

A

Add OH to the same carbon CH2CH3 is on

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25
Q

R–CH3 –1.B2H6/2.H2O2, NaOH–>

A

CH3 up and OH is added one carbon down from CH3 pointing down

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26
Q

Hg(OAc)2, H2O followed by NaBH4

A

Adds an OH where a double bond was

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27
Q

HCl

A

Adds Cl to most substituted carbon

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28
Q

Nucleophile that adds an OH to a double bond

A

H2O

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29
Q

H2O, H2SO4/HgSO4

A

Creates a ketone on the carbon that had double bonds closest to the ring

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30
Q

Propene to Propanol

A

B2H6, followed by H2O2, NaOH

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31
Q

Adding Br2 to (E)-3-hexene

A

One meso compound

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32
Q

R-CH3 –1.Hg(OAC)2, H2O/2. NaBH4–>

A

OH added to same carbon as CH3

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33
Q

Furan —Br2/CH3OH–>

A

Adds OCH3 next to O and Br next to OCH3

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34
Q
  1. R-BH/2. H2O2, NaOH
A

Adds aldehyde at the very end of the double bond

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35
Q

R-C (triple bonded)CH –> R-Ketone

A

H20,H2SO4/ HgSO4

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36
Q

A compound with two double bonds + HCl + CL2

A

Cl on each of the double bonds

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37
Q

R-CH3 –HCl–>

A

Cl adds to the same carbon as CH3

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38
Q

Double bond in a ring —> Epoxide

A

RCO3H

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39
Q

Butene —CHCl3/(CH3)3COK–>

A

Dimethyl cyclopropane with the CH3’s pointing it two different directions and 2 Cl’s at the top

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40
Q

R-CH3 —Br2/H2O–>

A

CH3 and OH on one carbon (CH3 up OH down) and Br (up) one carbon down

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41
Q

Different compounds with the same molecular formula

A

Isomers

42
Q

Isomers that have a different atom connectivity

A

Constitutional Isomers

43
Q

Isomers that have the same connectivity but differ in the arrangement of their atoms in space

A

Stereoisomers

44
Q

Stereoisomers that are nonsuperimposible mirror reflections of each other

A

Enatiomers

45
Q

Stereoisomers that are not mirror images of each other

A

Diastereomers (two molecules switched)

46
Q

A mixture of two enantiomers in equal concetrations

A

Racemic

Optically inactive

47
Q

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.

A

Meso

48
Q

Nucleophile attacks carbon bound to electronegative atom

A

Substitution Reactions

49
Q

Nucleophile can be a base and react with acidic protons of alkyl substrates

A

Elimination

50
Q

! step
Bimolecular
Rate is 1st order
Inversion occrus

A

Sn2

51
Q

2 steps
Ionization of alkyl substrate then reacts with nucleophile
Unimolecular
sp2 tetrahedral

A

Sn1

52
Q

NuH + X-

A

E2

53
Q

compound + NuH or compound + X-

A

E1

54
Q

Primary
Strong (like OH-) or Weak base (like Cl-)
Good Nucleophile

A

Sn2

55
Q

Primary
Strong Base (like OH-)
Non-nucleophilic bases

A

E2

56
Q

Secondary

Strong (like OH-) or Weak Base (like Cl-)

A

Sn2

57
Q 
Secondary
Poor Nucleophile (like H2O or HOR)
A

Sn1/E1 (slow), in polar, protic solvents

58
Q 
Tertiary
Strong base (like OH-)
A

E2

59
Q 
Tertiary
Weak base (like Cl-)
A

Sn1/E1 in polar, protic solvents

60
Q 
Tertiary
Poor Nucleophile (like H2O or ROH)
A

Sn1/E1 in polar, protic solvents

61
Q

O-H and N-H Frequency

A

3400

62
Q

C-H (sp3)

A

3000-2850

63
Q

C-H (sp2)

A

3000-3100

64
Q

C-H (sp)

A

3300

65
Q

C (triple bond) C and C (triple bond) N

A

2100

66
Q

C=O

A

1700

67
Q

C=C, aromatic C-C

A

1600

68
Q

Aromatic C-C

A

1500

69
Q

atom with 4 bonds

A

sp3

70
Q

atom with 3 bonds

A

sp2

71
Q

atom with 2 bonds

A

sp

72
Q

atom with 1 bond

A

s

73
Q

Carbocation stability

A

Tertiary > Secondary > Primary > Vinyl

74
Q

Ranking acids

A

EN > Distance from EN molecule> No EN molecule

75
Q

pH of 12

A

Deprotonates

76
Q

Acidity

A

HI>HBR, HCl, HF

77
Q

Larger atom

A

More nucleophilic

78
Q

Allylic and Benzylic halides undergo

A

Sn2 faster

79
Q

If catalyzed by acid, and nuc = primary amine

A

C-N imine

80
Q

If catalyzed by acid and nuc = secondary amine

A

C=C enamine

81
Q

Strong basic nuc like grignard or metal halides

A

1,2 addition

82
Q

Weak basic nut like R2CuLi

A

1,4 addition

83
Q

Stability of organic radicals

A

Allylic/Benzylic > tertiary alkyl > secondary alkyl > primary alkyl > methyl > vinylic/aryl

84
Q

Initiation

A

Generates radicals

Step 1

85
Q

Propagation

A

Radical reacts with stable molecule to produce a new radical

Step 2

86
Q

Termination

A

Destroys radicals and stops the reaction

Step 3

87
Q

Hydrogen atom count decreased

A

Oxidation

88
Q

Hydrogen atom count increased

A

Reduction

89
Q

Oxidizing agents

A

CrO3, K2Cr2O7, K2CrO4, KMnO4
Chromium used under acidic conditions
Potassium Permanganate used under basic conditions

90
Q

Oxidize only to aldehyde state

A

CrO3-2 pyridine, PCC, PDC

91
Q

Cleavage

A

HIO4 by ozone

92
Q

CH3MgBr

A

Oxidizes C=O and turns OCH3 into OH

93
Q

Hg(OAc)2, NaBH4/NaOH

A

Combines two molecules removing the double bond and the H from the OH

94
Q

NH3/H2,Pt

A

Oxidizes C=O and adds NH2

95
Q

KOH, CH2=CHCH2Br, H20 NaOH/heat

A

breaks apart two fused rings leaving only one c=c behind and adds NH2

96
Q

SoCl2/heat, NH3, Br2/NaOH

A

reduces ketone and replaces OH with NH2

97
Q

R-C(OH)HCH3

A

yellow precipitate

98
Q

NO2

A

meta directing

99
Q

Most to least reactive with NH3

A

Cl > anhydride > ester >amide

100
Q

SoCl2

A

Turns carboxylic acid to anhydride

101
Q

-OD/D2O

A

replaces only the alpha hydrogens

102
Q

NaCN

A

1,4 Addition

Organic Chemistry (8 decks)

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