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Organic Chemistry I > Chapter 2: Functional Groups and Nomenclature > Flashcards

Chapter 2: Functional Groups and Nomenclature Flashcards

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1
Q

what types of atoms are in hydrocarbons

A

only contain hydrogens and carbons

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2
Q

what are the 2 classifications of hydrocarbons

A

aliphatic and aromatic

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3
Q

What property about chemical bonding do Lewis models predict?

A

that electrons have wave properties

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4
Q

what are the two theories of bonding based on the wave of nature electrons

A

valence bond theory(came first)

molecular orbital theory

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5
Q

in terms of the valence bond model, when can electron pairs be shared

A

when half-filled orbital of one atom overlaps in phase with half-filled orbital of another

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6
Q

what is constructive interference

A

is between electron waves of two half-filled atomic orbitals

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7
Q

sigma bond

A

a bond in which the orbitals overlap along a line connecting the atoms

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8
Q

where do electrons in molecules reside

A

molecular orbitals (MOs)

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9
Q

where do electrons in an atom resiide

A

atomic orbitals (AOs)

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10
Q

how are MOs and AOs related

A

MOs are combinations of AOs, 2 electrons per MO

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11
Q

what combination generates one bonding orbital

A

additive combination of 2 atomic orbitals

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12
Q

what combination generates an antibonding orbital

A

subtractive combination of 2 atomic orbitals

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13
Q

symbol for antibonding

A

sigma star

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14
Q

what is the general formula for alkanes

A

C(n)H(2n+2)

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15
Q

what is the smallest/most abundant alkane

A

CH4- (methane)

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16
Q

what are the second smallest and most abundant alkanes

A

C2H6 (ethane)

C3H8 (propane)

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17
Q

what is natural gas composed of, and what special property do they all have

A

75% methane
10% ethane
5% propane

(have the lowest boiling points)

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18
Q

boiling point of methane

A

-160 C

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19
Q

boiling point of ethane

A

-89 C

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20
Q

boiling point of propane

A

-42 C

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21
Q

what set of alkanes are gases

A

C4 and lower

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22
Q

what alkanes are liquid

A

C4-C8

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23
Q

what alkanes are gases

A

C9 - C10

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24
Q

what makes alkanes different states of matter at room temp

A

as you get more carbon atoms, they increase to a warmer state

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25
Q

how many bonds do carbons in methane, ethane and propane have

A

4 bonds on each carbon

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26
Q

what are the bond angles of carbon in alkanes

A

109.5

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27
Q

what is interesting about the amount of bonds in carbon compared to normal electron configuration

A

normally carbon has 2 unfilled orbitals, and because in alkanes it needs 4 bonds, we must use hybridization

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28
Q

who and how did they propose hybridization

A

Pauling proposed a mixing or hybridization of the s and 3p orbitals to create 4 equal unfilled orbitals called sp3 orbitals

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29
Q

what do all 4 sp3 orbitals have in hybridization

A

equal energy!

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30
Q

how are 4 hybrid orbitals produced in hybridization

A

mixing 4 atomic orbitals

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31
Q

in examples such as sp3 hybrid orbitals in methane, why are they better than unhybridized 2s or 2p

A

they are stronger

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32
Q

sp3 bonding in methane

A

overlap between partially filled carbon sp3 orbital and partially filled s orbital of hydrogen

(h=1s and C=2sp3)

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33
Q

characteristics of C-C bond in ethane

A
  • like methane, formed by overlap of sp3 on each carbon
  • tetrahedral
  • 2 half filled sp3 orbitals on each C
  • orbitals overlap to form bond
  • the electrons on the C’s have opposite spins
  • 111 degrees
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34
Q

characteristics of bonding in Ethene

A
  • sp2 because sp3 is not possible (b/c 3 atoms are bonded to each carbon (not 4) so 3 hybrid orbitals form instead of 4)
  • planar
  • one p orbital is NOT hybridized (hence sp2 not sp3)
  • 120 degree angle
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35
Q

sp2 hybrids

A

2s and 2 2p orbitals are mixed to form 3 sp2 orbitals

  • trigonal planar arrangement
  • 2p orbitals are 1/2 fill
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36
Q

sigma bonding in ethylene

A
  • form C-H bonds by overlap of sp2 and s
  • form C-C bond by overlap of sp2 on each carbon
  • all sigma bonds, and unfilled p orbital is on each carbon atom
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37
Q

pi bonding in ethylene

A

after the C-C sigma bond, there is another C-C bond by the overlap of p orbitals on each carbon

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38
Q

sp hybridization and bonding in ethyne

A
  • linear
  • bond angle 180
  • 2 half dilled p orbitals, no hybridized
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39
Q

sp hybrid orbitals

A

the 2s and one of the 2p orbitals are mixed to form 2 sp orbitals

  • linear
  • 2py and 2pz remain half filled
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40
Q

hybridization of carbon sp3

A
  • 4 atoms

- bond angle = 109.5

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41
Q

hybridization of carbon sp2

A
  • 3 atoms
  • bond angles = 120
  • one C-C pi bond
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42
Q

hybridization of carbon sp

A
  • 2 atoms
  • bond angles = 180
  • 2 C-C pi bonds
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43
Q

what does n mean if it is before the name of something

A

normal, or unbranched

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44
Q

what alkanes have only 1 isomer

A

CH4

C2H6

C3H8

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45
Q

how many isomers for C4H10 and what type are they

A

2, constitutional

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46
Q

what are n-alkanes

A

straight-chain alkanes with general formula

CH3(CH2)nCH3

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47
Q

n-Pentane

A

is CH3CH2CH2CH2CH3

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48
Q

n-hexane

A

CH3CH2CH2CH2CH2CH3

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49
Q

can you abbreviate in alkanes

A

yes

ex)
CH3(CH2)3CH3

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50
Q

what alkanes have 1 isomer

A

CH4
C2H6
C3H8

51
Q

what alkane(s) have 2 isomers

A

C4H10

52
Q

what alkane(s) have 3 isomers

A

C5H12

53
Q

what alkane(s) have 5 isomers

A

C6H14

54
Q

what alkane(s) have 9 isomers

A

C7H16

55
Q

what alkane(s) have 18 isomers

A

C8H18

56
Q

what alkane(s) have 35 isomers

A

C9H20

57
Q

what alkane(s) have 75 isomers

A

C10H22

58
Q

methane

A

-1 carbon

CH4

59
Q

ethane

A

-2 carbons

C2H6

60
Q

propane

A

3 carbons

C3H8

61
Q

butane

A

4 carbons

C4H10

62
Q

pentane

A

5 carbons

C5H12

63
Q

hexane

A

6 carbons

C6H14

64
Q

heptane

A

7 carbons

C7H16

65
Q

octane

A

8 carbons

C8H18

66
Q

nonane

A

9 carbons

C9H20

67
Q

decane

A

10 carbons

C10H22

68
Q

undecane

A

11 carbons

CH3(CH2)9CH3

69
Q

dodecane

A

12 carbons

CH3(CH2)10CH3

70
Q

tridecane

A

13 carbons

CH3(CH2)11CH3

71
Q

tetradecane

A

14 carbons

CH3(CH2)12CH3

72
Q

pentadecane

A

15 carbons

CH3(CH2)13CH3

73
Q

hexadecane

A

16 carbons

CH3(CH2)14CH3

74
Q

heptadecane

A

17 carbons

CH3(CH2)15CH3

75
Q

octadecane

A

18 carbons

CH3(CH2)16CH3

76
Q

nonadecane

A

19 carbons

CH3(CH2)17CH3

77
Q

Icosane

A

20 carbons

CH3(CH2)18CH3

78
Q

methyl

A

CH3

79
Q

methyline

A

CH2

80
Q

Methine

A

CH

81
Q

what are alkyl groups

A

substituents derived from alkanes (they lack 1 hydrogen at the point of attachment)

ex)
CH3CH2CH2CH2

82
Q

what are the classifications of carbon atoms

A

primary
secondary
tertiary
quaternary

83
Q

what type of carbon classification is easiest and most difficult to react with

A 
easiest = primary
hardest = tertiary

more carbon = harder

84
Q

how to label when substituents with 2 branches in addition to others are there

A

make sure that the first double branch is the lowest number (label “backwards” if needed)

85
Q

general formula for cycloalkanes

A

CnH2n

86
Q

how many degrees of unsaturation are assigned to each saturated ring in cycloalkanes

A

1 degree of unsaturation for structural purposes

87
Q

common name for 2-methylpropyl

A

isobutyl

88
Q

common name for 1-methylpropyl

A

sec-butyl

89
Q

common name for 1,1-dimethylthyl

A

tert-butyl

90
Q

how do you do naming when you have 2 or more substituents to name

A

put them in alphabetical order, but ignore the prefix (such as di or tri) when alphabetizing

91
Q

naming substituted cycloalkanes

A

same as naming branched alkanes BUT

if there is only 1 substituent, DO NOT LABEL WITH A 1 !!

92
Q

what happens if the cycloalkane ring has fewer carbons than the substituent does?

A

the ring becomes the substituent, and the substituent becomes the parent

93
Q

what is petroleum and how many hydrocarbons does it have

A

a liquid micture

150 hydrocarbons (half are alkanes or cycloalkanes)

94
Q

what is cracking (thermal and catalysts)

A

cleaving carbon-carbon bonds in heavy alkanes

heat=thermal
catalysts = catalytic

95
Q

what is reforming

A

converts hydrocarbons in petroleum to aromatic, and highly branched alkanes because they are better automotive fuels than unbranched alkanes/cycloalkanes

96
Q

what factor in the liquid phase will affect the boiling point of that liquid

A

the attractive forces (van der waals forces)

97
Q

what are the 3 types of vander waal forces

A
  • dipole dipole (includes hydrogen bonding)
  • induced dipole dipole
  • induced dipole induced dipole
98
Q

what type of bond do alkanes have and why

A

temporary induced dipole induced dipole

because alkanes have no strong dipoles

99
Q

what type of alkanes have more induced dipole induced dipole interactions

A

long chain alkanes

100
Q

what is the relationship between carbon chain length and boiling point

A

the longer the chain, the higher the boiling point (needs more NG to move to the next phase)

101
Q

what is the relationship between boiling point and molecular weight in unbranched (n) alkanes

A

boiling point will increase as molecular weight increases

102
Q

why do branched alkanes have a lower boiling point than unbranched

A

because they have a lower surface area and this a lower boiling point

103
Q

what does it mean when we say that solid n-alkanes are soft low melting solids

A

the same intermolecular forces hold the molecules together in the solid state

104
Q

solubility of alkanes in water

A

alkanes and all hydrocarbons are basically insoluble in water and hydrophobic

105
Q

do alkanes float or sink

A

float

106
Q

what is the acidity of alkanes and cycloalkanes like

A

they are like hydrocarbons and very weak

they have the lowest pKa in hydrocarbons

107
Q

what type of hybridization is most and least acidic for hydrocarbons

A 
sp = most acidic
sp3 = least acidic
108
Q

combustion of hydrocarbons

A

hydrocarbon + O2 = Co2 + H2O

exothermic

109
Q

how many molecules of CO2 and how many molecules of H2O does combustion of isomers C8H18 create

A

8 CO2
9 H2O

YET DIFFERENT AMOUNTS OF ENERGY

110
Q

what is the relationship between the different amounts of energy in combustion of isomers compared to relative energies of isomers

A

because the energy of combusion is different, this signals that the relative energyies of isomers must be different too

111
Q

what is the relationship between energy released and stability of isomers

A

least stable isomers will have the highest energy

the most stable isomers will have the least energy released

112
Q

how can you calculate the oxidation state of CHO’s

A 
H = +1
O = -2

then you can calculate C

113
Q

what does the total sum of the oxidation states of all atoms in any given species equal

A

the net charge on that species

114
Q

what is the oxidation number for group 1A metals

A

+1

115
Q

what is the oxidation number for group 2A metals

A

+2

116
Q

what is the oxidation number for group 3A

A

-3

117
Q

what is the oxidation state of group 6A

A

-2

118
Q

what is the oxidation state of group 7A

A

-1

119
Q

what is the oxidation state of C in CH3Cl and CH3OH

A

-2

120
Q

what is the oxidation state of C in CH4 and CH3Li

A

-4

121
Q

what does the oxidation of carbon correspond to

A

an increase in bonds between C and O

a decrease in the number of H-O bonds

122
Q

what does reduction correspond to

A

an increase in C-H bonds

a decrease in C-O bonds

123
Q

in general, what does increasing the oxidation state of carbon do

A

it decreases the hydrogen content

Organic Chemistry I (9 decks)

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