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CHEM 261 > CHEM 261 > Flashcards

CHEM 261 Flashcards

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1
Q

How big is an Angstrom?

A

10^ -8 cm

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2
Q

What are the 2 basic principles of chemistry?

A

a) Like Charges Repel
b) Atoms Want An Inert Gas Configuration

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3
Q

What is Avogadro’s number?

A

6.022 e 23

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4
Q

Isoelectronic meaning

A

Equal number of electrons

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5
Q

What is a pure compound?

A

A compound with no change in physical properties upon further purification?

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6
Q

4 Properties of Organic Compounds

A
  1. Non-polar
  2. Soluble in oil
  3. Low mp and bp
  4. Burn in O2
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7
Q

STP Conditions

A

760 mmHg (1 atm)
0 degrees C (273 K)

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8
Q

Degenerate Orbitals Have _________.

A

The same energy

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9
Q

What is the Aufbau Principle?

A

Electrons fill the lowest energy orbitals first, with opposite spins

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10
Q

What is the Pauli Exclusion Principle?

A

Max 2e- per orbital

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11
Q

If an orbital contains an “s” component, it must be ____.

A

Sigma

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12
Q

What type of orbital contains only “p” components?

A

Pi

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13
Q

Is a bonding or antibonding orbital higher in energy?

A

Antibonding

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14
Q

What is the ideal bond angle for a tetrahedral complex?

A

109 degrees

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15
Q

What is the ideal bond angle of an sp2 hybridized bond?

A

120 degrees

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16
Q

Do lone pairs or radicals count as an e- group for shape?

A

Yes

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17
Q

What is the longest bond type?

A

X-H, C-C, C=X, C=C

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18
Q

What does a bold wedge mean?

A

Towards you

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19
Q

What does a dashed line mean?

A

Away from you

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20
Q

What functional groups are in testosterone?

A

Methyl, methylene, ketone, alcohol

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21
Q

What functional groups are in estradiol?

A

Methyl, methylene, phenol

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22
Q

What must be considered to properly depict molecules?

A

Formal Charge

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23
Q

What is the formula to calculate formal charge?

A

of protons in nucleus
- e- in inner shell (usually 2)
- unshared e- in outer shell
- 0.5 x shared e-

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24
Q

Are resonance structures rapidly interconverting structures?

A

Nope

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25
Q

What is electronegativity?

A

An atoms desire for electrons

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26
Q

Order the 3 Intermolecular forces

A

Strongest

Hydrogen bonding
Dipole-dipole
London Dispersion Forces

Weakest

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27
Q

What is necessary for hydrogen bonding to occur?

A

A lone pair on the halogen electron acceptor (electronegative atom)
Hydrogen must be directly attached to halogen

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28
Q

What is the name for CHCl3

A

Chloroform

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29
Q

What is the name for CH2Cl2

A

Dichloromethane / methylene chloride

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30
Q

What is the name for CCl4

A

Carbon tetrachloride

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31
Q

What is boiling point determined by?

A

Increases with size

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32
Q

How many kJ are in a kcal?

A

0.239

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33
Q

What is an intermediate?

A

A species that can be detected that exist for a short period of time
(not a TS)

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34
Q

What is a Bronsted Lowry acid?

A

A proton donator

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35
Q

What is a Lewis acid?

A

An electron pair acceptor

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36
Q

Are all Bronsted Lowry acids/bases Lewis acid/bases?

A

Yes –> but it is not reversible

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37
Q

What is the pKa of ammonia (NH3)?

A

36

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38
Q

What is the pKa of ammonium (NH4)?

A

9.3

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39
Q

What is the pKa of water?

A

15.7

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40
Q

If an acid has a higher pKa is is more/less acidic?

A

Less acidic

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41
Q

What is the pKa of alkanes?

A

45/46

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42
Q

What makes a compound visible under UV light?

A

Conjugated bonds

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43
Q

Compounds that contain only C and H are _____.

A

Hydrocarbons

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44
Q

What forces hold alkanes together?

A

Dispersion forces

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45
Q

What does an n in front of a compound mean?

A

Normal [unbranched (straight) chain with functional group in 1 position]

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46
Q

What is an iso group?

A

C with two methyl groups attached

47
Q

Do constitutional isomers have the same name?

A

No, then they would be steroisomers

48
Q

Steps for naming alkanes

A

a) Find longest chain of carbons
b) Number from end (lowest number to side with first branch)
c) Name groups (drop -ane and add -yl)
d) Prefix with number ex. di (separate with hyphens)
e) Alphabetical order

49
Q

One rule for naming cycloalkanes

A

Start of point of maximum branching and number in direction of next branch

50
Q

Degrees of unsaturation can be found by number of _____ and _____.

A

a) Rings and double bonds
b) Formula:
[(2 x C + 2) - H + N - X] / 2

51
Q

What are enantiomers?

A

Non-superimposable mirror images

52
Q

As chain length / surface area increases, bp ______.

A

Increases

53
Q

Do even or odd numbered carbons pack better?

A

Even

54
Q

Names of the alkanes 11-20

A

undecane
dodecane
tridecane
tetradecane
pentadecane
hexadecane
heptadecane
octadecane
nonadecane
eicosane

55
Q

Suffix for alkanes with 20 carbons

A

Cosanes

56
Q

Suffix for alkanes with 30+ carbons

A

Contanes

57
Q

Atomic mass of Helium

A

4.00

58
Q

Atomic mass of Lithium

A

6.94

59
Q

Atomic mass of Beryllium

A

9.01

60
Q

Atomic mass of Boron

A

10.81

61
Q

Atomic mass of Fluorine

A

19.00

62
Q

Atomic mass of Neon

A

20.18

63
Q

What is a primary carbon?

A

A carbon with only one substituent (not hydrogen)

64
Q

C-O-C group is called?

A

Ether

65
Q

C - C - H
=O group is called?

A

Aldehyde

66
Q

C = O
O group is called?

A

Ester

67
Q

Does an amide or an amine group contain a double bond?

A

Amide

68
Q

Is an eclipsed Newman Projection ever the most stable?

A

No - there is too much steric repulsion

69
Q

What is an anti conformation?

A

The most stable (staggered and largest groups are furthest apart)

70
Q

What is a gauche conformation?

A

Largest groups are close together but they are staggered.

71
Q

Are axial or equatorial groups the most stable?

A

Equatorial

72
Q

Why should the largest groups be equatorial?

A

To avoid 1-3 diaxial repulsions

73
Q

Diastereomers have (the) same/different physical properties?

A

Different

74
Q

What compound connects to form diamond?

A

Adamantanes

75
Q

What is a bridgehead?

A

An atom where rings fuse

76
Q

What must be added for halogenation reactions of alkanes?

A

Light

77
Q

What are the two types of alkane reactions, and furthermore the subtypes of one?

A

a) Combustion
b) Halogenation
i) radical (two radicals formed)
ii) ionic (one ion formed and one electrophile)

78
Q

What are the three steps of alkane halogenation?

A

Initiation
Propagation (2 steps)
Termination (3 steps)

79
Q

In alkane halogenation, what position does the halogen attach to?

A

The least substituted carbon

80
Q

Order radicals in order of stability

A

Most

Tertiary
Secondary
Primary
Methyl

Least

81
Q

What is the Hammond Postulate?

A

When something is more reactive, it is less selective.

OR

When something is less reactive, it is more selective.

82
Q

In an exothermic reaction, does the TS resemble the SM or the products more?

A

Starting materials

83
Q

Rules for naming alkyl halides

A

a) Start at longest chain with max number of halogens/branches

b) Number from the end to give halide the lowest number

84
Q

5 Physical Properties of Haloalkanes

A
  1. Dipole-dipole interactions
  2. Higher bp than alkanes
  3. Good solvents for organic compounds
  4. if % composition > 65% halogen; density 1.0g/mL
  5. Immiscible in water
85
Q

What is a stereogenic center?

A

Carbon with four different groups attached

86
Q

What is a meso compound?

A

An achiral compound that has stereogenic centers

87
Q

A clockwise center is _____ and a counterclockwise center is _____.

A

R, S

88
Q

The priority 4 group must be to the ______ for a center to be opposite.

A

Front

89
Q

When drawing an enantiomer, draw the same structure and _____ centers.

A

Invert/flip

90
Q

Formula for determining stereoisomers

A

2 ^ n

91
Q

What groups are towards you in a Fischer projection?

A

Horizontal

92
Q

What stereoisomer rotates in a plane of polarized light?

A

Enantiomers

93
Q

Dextrorotary means _______.
Levorotatory means _______.

A

Clockwise
Counter clockwise

94
Q

Mixture of enantiomers is _____.

A

A racemic mixture/racemate

95
Q

Two kinds of Substitution Reactions

A

a) Radical
b) Ionic
i) SN1
ii) SN2

96
Q

What is a nucleophile?

A

A positive seeking species (negatively charged)

97
Q

SN2 Mechanism

A

a) Bimolecular
b) Steric Bulk is the main barrier
c) Primary and Secondary are better
d) Charged or strong nucleophiles are better
e) Inverted Stereochemistry
f) Concerted
g) Rate is dependent on [Nu:] and [RX]

98
Q

SN1 Mechanism

A

a) Unimolecular
b) Carbocation stability is the main barrier
c) Tertiary are better
d) Neutral or weak nucleophiles are better
e) Mixed stereochemistry
f) Stepwise
g) Rate is dependent on [RX]

99
Q

Good Leaving groups

A

Sulfur thingy > I- > Br- > Cl-»> F-

100
Q

Poor leaving groups

A

F-
OH-
OR-
NR2 -
R: -
H: -

101
Q

How can bad leaving groups be made better?

A

By adding an acid

102
Q

What hybridization of carbon will not undergo substitution?

A

sp2

103
Q

Does a leaving group on a double bond leave?

A

No

104
Q

What is another name for an alkene?

A

Olefin

105
Q

What si another name for an alkyne?

A

Acetylene

106
Q

Rules for naming alkenes/alkynes

A

a) Find longest chain with max number of double or triple bonds
b) Number from end to give first multiple bond the lowest number
c) Drop -ane and add -ene/-yne

107
Q

Are trans and cis compounds the same molecule?

A

No, they are diastereomers

108
Q

Which takes priority, a double bond or a halogen?

A

Double bond

109
Q

E means same/opposite and Z means same/opposite

A

E means opposite and Z means same

110
Q

What is a C5 unit called?

A

Isoprene

111
Q

What is the pKa of alkenes?

A

~36

112
Q

What is the pKa of alkynes?

A

~26

113
Q

What are the names of isoprene containing compounds? Name the first 6.

A

Terpenoids or Isoprenoids

  1. Hemiterpene
  2. Monoterpene
  3. Sesquiterpene
  4. Diterpene
  5. Sesterterpene
  6. Triterpene
114
Q

A reaction takes an acid from pKa 26 to pKa 36, will this work?

A

Yes, because reactions always go from a stronger acid (lower pKa) to a weaker acid.

CHEM 261 (1 decks)

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