Review Flashcards

1
Q

Chemical bonding is dictated by […]

A

Valence electrons

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2
Q

What are valence electrons?

A

Electrons in the outermost shell (equal to the group #)

Rule of thumb: atoms form bonds in a manner that fills outer shell (e.g., octet rule)

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3
Q

Which ions tend to form ionic bonds?

A
Easier for sodium to lose 1 electron and chlorine to gain 1 electron for each to fill outer shell with 8 electrons.
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4
Q

How is formal charge calculated?

A

Charge = (# valence e-) - (# bonds) - (# unshared e-)

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5
Q

Briefly - what is VSEPR theory?

A

Bonded atoms/electron pairs try to maximize space/repulsions and determine the shape of the molecule.

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6
Q

What are the 4 numbers that describe atomic orbitals?

A

Energy level or shell (n): 1, 2, 3, …
**Angular momentum; defines shape (s - sphere; p = lobes) (l): **0 (‘s’ orbital); 1 (‘p’ orbital); 2 (‘d’ orbital), …
Magnetic quantum number (m): values from -l to +l (thus, an s orbital has m = 0, while a p orbital has m = -1, 0, +1)
Spin number (s): each electron has spin

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7
Q

Describe atomic orbitals energy level diagrams.

A
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8
Q

Describe atomic orbital hybridization to form molecular orbitals.

A
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9
Q

Rotation of atoms around a sigma bond affects bond energy.
True or False?

A

False.

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10
Q

Rotation of atoms around a sigma bond does not affect the bond energy.
True or False?

A

True.

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11
Q

sp3 hybridization

A

Single bonding

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12
Q

sp2 hybridization

A

Double bonding

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13
Q

Pi bonds result from:

A

Overlap of 2p atomic orbitals

Rotation about a pi bond is disfavoured - imposes planar geometry

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14
Q

Pi bonds are weaker than sigma bonds.
True or False?

A

True.

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15
Q

Sigma bonds are weaker than pi bonds.
True or False?

A

False.

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16
Q

sp hybridization

A

Triple bonding

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17
Q

What is resonance and when is it possible?

A

Delocalized molecular orbitals; only possible with overlapping, parallel p orbitals

a.k.a. conjugation
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18
Q

Describe the bond dissociation energies and lengths.

A
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19
Q
A

Alkane

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20
Q
A

Alkene

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21
Q
A

Conjugated alkene

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22
Q
A

Alkyne

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23
Q
A

Arene

e.g., benzene

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24
Q
A

Ketone

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25
Q
A

Aldehyde

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26
Q
A

Carboxylic acid

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27
Q
A

Ester

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28
Q
A

Acid Halide

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29
Q
A

Amide

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30
Q
A

Peroxy Acid

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31
Q
A

Anhydride

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32
Q
A

Primary Amine

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33
Q
A

Secondary Amine

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34
Q
A

Tertiary Amine

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35
Q
A

Alcohol

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36
Q
A

Ether

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37
Q
A

Thiol

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38
Q
A

Thioether

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39
Q

Alkane

40
Q

Alkene

41
Q

Conjugated alkene

42
Q

Alkyne

43
Q

Arene

e.g., benzene

44
Q

Ketone

45
Q

Aldehyde

46
Q

Carboxylic acid

47
Q

Ester

48
Q

Acid Halide

49
Q

Amide

50
Q

Peroxy Acid

51
Q

Anhydride

52
Q

Primary Amine

53
Q

Secondary Amine

54
Q

Tertiary Amine

55
Q

Alcohol

56
Q

Ether

57
Q

Thiol

58
Q

Thioether

59
Q

Define: polarity

A

Uneven sharing of electron results in a dipole

60
Q

Describe the order of increasing electronegativity.

More capable of carrying negative charge

A

S = C < N < O < F

61
Q

List non-covalent interactions from strongest to weakest.

A
  • Ion-ion (very strong)
    • Lattice interactions (188 kcal/mol) stronger than typical covalent bonds (100 kcal/mol)
  • Ion-dipole (moderately strong)
    • Greater the charge = stronger
  • Dipole-dipole (weak)
    • Polar interactions
  • Dipole-induced dipole (quite weak)
  • Instantaneous dipole-induced dipole (very weak)
    • Non-polar interactions (a.k.a. London forces)
62
Q

Describe hydrogen bonding.

A
  • A special kind of dipole-dipole
  • H-bond donor must be an electronegative atom (N, O, F)
  • H-bond acceptor must be an electronegative atom
  • H-bond strength of ~2-8 kcal/mol (distance/orientation dependent)
63
Q

Describe the strength of hydrogen bonds in water.

A

O-O distance is dependent on H-bond strength of water

64
Q

Describe the molecular geometry of water.

A
  • Bent tetrahedral geometry is crucial to water’s special properties and ability to form hydrogen bond networks
65
Q

Describe hydrogen bonding in ice.

66
Q

Describe hydrogen bonding with food components. [5]

67
Q

Briefly describe water interaction with proteins.

A

Bound water can be crucial to enzyme activity and stability of folded structure.

Papain (protease) "water bridge"
68
Q

Describe the hydrophobic effect.

A

Driven by increased entropy (lower energy) due to the release of solvation water from non-polar groups.

69
Q

What is the general formula for CHO?

70
Q

What are sugars?

A
  • Polyalcohols with an aldehyde or ketone group; named according to the type of carbonyl functional group
71
Q

What is an enantiomer?

A

Non-superimposable mirror images

72
Q

What is the difference between D and L forms of sugar?

A

D = hydroxyl of highest # chiral C is on right side of Fischer projection (by convention)

73
Q

L-sugars are rare - only two are commonly found in food (as polysaccharides). They are:

A
  • L-arabinose
  • L-galactose
74
Q

What are the D-aldose sugars?

75
Q

What are the D-ketose sugars?

76
Q

How do sugars form rings?

A

Base catalyzed

77
Q

What are the bonds in each disaccharide?

A

Lactose: Beta-(1-4) linkage between galactose-glucose
Sucrose: alpha-(1-2) linkage between glucose-fructose
Maltose: alpha-(1-4) linkage between glucose-glucose

78
Q

When is a sugar non-reducing?

A

When a glycosidic linkage forms between two anomeric carbons

A reducing sugar is one that reduces another compound and is itself oxidized; that is, the carbonyl carbon of the sugar is oxidized to a carboxyl group. A sugar is classified as a reducing sugar only if it has an open-chain form with an aldehyde group or a free hemiacetal group.

79
Q

Describe polysaccharides.

80
Q

What is amylose?

A

Mostly linear polysaccharide with a reducing end and a non-reducing end

81
Q

Describe the structure of amylose.

A

Left-handed double helix at 6 glucose molecules per turn

82
Q

What is amylopectin?

A

Branded polysaccharide

83
Q

Describe the structure of amylopectin.

A
  • Similar to glycogen, which is > highly branched; smaller
  • Branches also form helical structure, similar to amylose
  • Waxy starches consist mainly/only of amylopectin
84
Q

What are starch granules?

85
Q

Starch gelatinization is irreversible.
True or False?

86
Q

Starch gelatinization is reversible.
True or False?

87
Q

Starch granules are insoluble in ‘cold’ water’.
True or False?

88
Q

Starch granules are soluble in ‘cold’ water.
True or False?

89
Q

Describe starch gelatinization.

A
  • Heating in water induces gelatinization:
    • Water penetrates into amorphous regions
    • Disruption of molecular order
    • Loss of crystallinity
    • Leaching of amylose
    • Granules swell many times their normal size
    • Easily disrupted by stirring
    • Produce a viscous mass (starch paste)
The viscosity rises until the granules are hydrated to their maximum.
90
Q

What is the difference between saturated and unsaturated fatty acids?

91
Q

Why does unsaturation add ‘kinks’?

92
Q

Name 3 important PUFAs.

93
Q

What are acylglycerols?

93
Q

Describe how the melting point of a fatty acid is affected by chain length and saturation.

A
  • MP increases with chain length (because the intermolecular forces, such as van der Waals forces, are stronger with longer chains)
  • MP decreases with unsaturation (double bonds create kinks in the chain, preventing the molecules from packing closely together; weaker molecular packing reduces the strength of intermolecular forces)
93
Q

What is the difference bewteen simple and mixed triacylglycerols?

94
Q

What is a phospholipid?

A
  • An acylglycerol with one hydroxyl group (sn-3) esterified to a phosphate group
95
Q

What is the primary component of cellular membranes?