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ORGANIC CHEMISTRY > Content OC > Flashcards

Content OC Flashcards

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1
Q

electron domain: 4

A

geometry: linear
bond angle: 180
hybrid.: sp

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2
Q

electron domain: 3

A

geometry: trigonal planar
bond angle: 120
hybrid.: sp2

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3
Q

electron domain: 2

A

geometry: tetrahedral
bond angle: 109.5
hybrid.: sp3

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4
Q

single bond

A

one sigma

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5
Q

double bond

A

one sigma
one pi

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6
Q

triple bond

A

one sigma
two pi

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7
Q

determining greatest resonance contributer

A

the most stable will have a full octet on every atom

the most stable will have the smallest number of charges

the most stable will have neg. charges on the most electroneg. atoms and positive charge on the least electroneg. atoms

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8
Q

order of stability in newman projections

A

staggered > gauche > eclipsed axi

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9
Q

axial vs equatorial

A
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10
Q

equatorial bonds are more ________

A

stable ( lower energy ) than axial

place largest sub on equatorial to get greatest stability

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11
Q

cis

A

two subs. in the same direction

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12
Q

trans

A

two subs. in opposite direction

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13
Q

a lewis acid ______ electrons

A

accepts

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14
Q

a lewis base _______ electrons

A

donates

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15
Q

the stronger the acid, ______

A

the weaker/ more stable the conjugate base

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16
Q

the stronger the base, ________

A

the more stable/weaker the conjugate acid

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17
Q

pks for organic compounds

A
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18
Q

the more positively charged,

A

the more acidic

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19
Q

the more negatively charged,

A

the more basic

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20
Q

if all factors are about the same, then hydrogens acidity increases as the atom that it’s bonded to:

A

goes left to right across a row
goes down a column

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21
Q

electron withdrawing groups increase

A

acidity

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22
Q

electron donating groups decrease

A

acidity

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23
Q

s-orbitals tend to be more electroneg., so the more “s” character :

A

the stronger the acid

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24
Q

C
A
R
D
I
O

A

Charge: positively charged compounds are typically more acidic, negatively charged compounds are more basic

Atom: the more electroneg./ larger the atom with a negative charge, the more acidic the hydrogen is

Resonance: the more resonance stabilized the conjugate base, the stronger the acid

Dipole Induction: electron withdrawing groups increase acidity, electron donating groups decrease acidity

Orbitals: the more s-character an atom has, the more electroneg it is, and the more acidic hydrogens bonded to it will be sp3<sp2< sp

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25
Q

as KA increases, pka ____, and acid strength ______

A

decreases

increases

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26
Q

if the pH of the solution is lower than the pKa of the functional group,

A

the functional group will be protonated

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27
Q

if the pH of the solution is higher than the pKa of the functional group,

A

the functional group will be deprotonated

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28
Q

amino acid if protonated ( pH < pKa )

A
  • NH3 +
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29
Q

amino acid if deprotonated ( pH > pKa )

A

-NH2

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30
Q

carboxylic acid group if protonated ( pH < pKa )

A
  • COOH
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31
Q

carboxylic acid group if deprotonated ( pH > pKa )

A
  • COO-
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32
Q

hydroxyl group if protonated ( pka > pH )

A

-OH

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33
Q

hydroxyl group if deprotonated ( pH > pKa)

A

-O-

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34
Q

when counting how many steroisomers one chiral molecule can have, use the equation:

A

2^n

n is the number of chiral centers

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35
Q

chiral molecules have the ability to

A

rotate olan polarized light when placed in a special machine called a polarimeter

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36
Q

Molecules that do not rotate plane-polarized light are called

A

achiral or inactive

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37
Q

there are 3 types of optically inactive ( or achiral ) molecules:

A
  1. 50/50 racemic mixture of two enantiomers ( racemic mixture )
  2. molecules that do not have stereochemistry in the them
  3. meso compounds
38
Q

meso compound

A

any molecule with 2 or more chirality centers, and a line of symmetry

an enantiomer of a meso compound is exactly the same as the original molecule ( 2 are superimposable )

39
Q

fisher projection

A

look up pls

40
Q

a BIG point peak at 1700+/- 50 cm-1

A

C=O

41
Q

a LARGE, broad trough far to the left for alcohols and on top of 3000 cm-1 for carboxylic acids

A

OH

42
Q

big, pointy peaks coming straight down around 3000 cm-1

A

C-H’s

43
Q

a sharp peak to the left of 3000 ( around 3200-3500)

A

N-H
(one peak for -NH, two peaks for -NH2)

44
Q

medium sized peak at -2200

A

C (tripled bond) N
- a nitrile

45
Q

vampire teeth at 1500-1600 and 1300-1400

A

NO2

46
Q

carbon-carbon double bonds are found in which IR region?

A

1600 cm-1

47
Q

carbon-nitrogen double bonds (imines) are found in which IR region?

A

1600 cm-1

48
Q

UV-Vis spectroscopy

A

is used mostly to analyze compounds with conjugated double bonds

49
Q

mass spectroscopy

A

technique used to determine a compounds mass

50
Q

degree of unsaturation

A

(A-B) /2

a is the number of hydrogen atoms your compound would have if it didnt have any double bonds or rings

b is the number of hydrogen atoms your compound in question actually has

51
Q

degree of unsaturation

A

c- (h/2) - (x/2)+ (n/2) +1

52
Q

more negatively charged a carbon

A

further down to the right of 13C-NMR spectroscopy

53
Q

more positively charged a carbon

A

further down to the left of 13C-NMR

54
Q

Carbonyl carbons
- esters, amides, and carboxylic acids
- aldehydes and ketones

Kind of C-NMR?

A

160 - 180 ppm
> 200 ppm

55
Q

TMS (tetramethysilane)

Kind of C-NMR?

A

0 ppm

not part of your compound?

56
Q

1 H - NMR spectroscopy

carboxylic acid and amide H’s

A

12,13,14

57
Q

1 H - NMR spectroscopy

phenols and aldehydes

A

10

58
Q

1 H - NMR spectroscopy

aromatic land ( H’s stuck to benzene)

A

6,7,8

59
Q

1 H - NMR spectroscopy

double bonds land

A

4,5,6

60
Q

1 H - NMR spectroscopy

single bond land

A

1,2,3,4,5

61
Q

1 H - NMR spectroscopy

Alcohol and amine H’s

A

0.5-5.5 ppm

62
Q

1 H - NMR spectroscopy

TMS

A

0

not apart of your compound!

63
Q

1 H - NMR spectroscopy

the more + charged =

A

more left, downfield

64
Q

hydrogens get split by neighboring hydrogens. To figure out splitting,

A

count all the hydrogens next door in all directions and add (n+1 rule)

65
Q

Intra-molecular Forces (within)

Covalent

A

two non metals atoms bond together and share electrons

66
Q

Intra-molecular Forces (within)

Ionic bonds

A

metal bond to nonmetals and a transfer of electrons occurs

67
Q

Intra-molecular Forces (within)

metallic bonds

A

metal atoms bond together and electrons flow freely around their nuclei

68
Q

Inter- molecular Forces ( between molecules )

ion dipole

A

ionic compounds interacting with polar compounds

69
Q

Inter- molecular Forces ( between molecules )

hydrogen bonding

A

H-O

H- N

H-F

70
Q

Inter- molecular Forces ( between molecules )

dipole dipole

A

H-Cl

C-O

S-H

71
Q

Inter- molecular Forces ( between molecules )

dispersion forces

A

hydrocarbons

single elements

non polar molecules

72
Q

tollens test

A

reagent: Ag,O/NH3 or Ag(NH3)2

function group tested: aldehydes

positive result: sides of flask are coated with a silver mirror

73
Q

iodoform test

A

reagent: I2/OH

functional group tested: methyl ketones

positive result: yellow percipitate forms (CHI3)

74
Q

silver nitrate in alcohol

A

reagent: AgNO3 in alcohol

function group tested: alkyl halide s

positive result: precipitate of Ag compound formed

75
Q

bromine test

A

reagent: Br2/CCl4

Functional group tested: alkenes and alkynes

positive result: brown color of bromine disappears

76
Q

baeyer test

A

reagent: dilute KMnO4

functional groups tested: alkenes and alkynes

positive result: purple solution turns to brown precipitate

77
Q

Jones Test

A

reagent: CrO3 / H2SO4

functional groups tested: 1 and 2 alcohols

positive result: orange reagent turns blue-green

78
Q

Lucas Test

A

reagent: ZnCl2/HCl

Functional groups being tested: 2,3 and benzylic alcohols

positive results: cloudy solution initially, then separate layer forms

79
Q

metallic

A

Interaction: Metallic Bonding

Properties: Variable hardness and melting point, conductive

Examples: Fe, Mg

80
Q

Ionic

A

Interaction: Ionic

Properties: High melting point, brittle, hard

Examples: NaCl, MgO

81
Q

Network

A

Interaction: Covalent Network

Properties: High melting point, hard, non conductive

Examples: C (diamond, graphite)
SiO2 (quartz)

82
Q

Molecular

A

Interactions: H Bonding, dipole dipole, London dispersion

Properties: Low melting point, non conductive

Examples: H2, CO2

83
Q

the stronger a molecules intermolecular forces:

A

higher the BP

higher its MP

lower its VP

84
Q

melting points help determine a compounds

A

purity

85
Q

for carboxylic acids, extract with

A

NaOH or NaHCO3

86
Q

for phenols, extract with

A

NaOH

87
Q

for amines, extract with

A

aqueous HCl

88
Q

separates mixtures of 2 or more volatile liquids

A

distillation

89
Q

used when 2 volatile liquids have boiling points that are closer together

A

fractional distillation

90
Q

dissolves an impure compound in hot solvent and gradually precipitates the pure compound as the solution cools down

A

recrystallization

91
Q

glass liquid chromatography

A

used to determine the relative abundance of each compound in a liquid mixture

separates components in liquid mixture by boiling point

lowest boiling point comes off the fastest

92
Q

thin layer chromatography

A

separates compounds by their solubility in the solvent (polarity)

most soluble compound travels the fastest and furthest up the plate

usually uses polar plates and non polar solvent

compound that travels the furthest with non polar solvent is the most non polar compound

retention factor (Rf) is the number we use to tell how far up the TLC plate a compound travels

ORGANIC CHEMISTRY (13 decks)

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