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Chemistry 1 > Lectures 9-21 > Flashcards

Lectures 9-21 Flashcards

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1
Q

drawing Lewis Structures

A

sum valence electrons, place single bond between atoms, complete octet rules, add lone pairs/multiple bonds, place extra electrons in d orbitals if necessary

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2
Q

the more resonance structures a molecule has,

A

the more stable it is

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3
Q

bond order

A

0.5 x (number of delocalised electrons/number of bonds containing delocalised electrons)

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4
Q

Lewis Acids

A

can accept a pair of unbonding electrons

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5
Q

all species with an odd number of electrons are

A

radicals

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6
Q

number of electron pairs: linear

A

2

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7
Q

number of electron pairs: trigonal planar

A

3

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8
Q

number of electron pairs: tetrahedral

A

4

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9
Q

number of electron pairs: trigonal bipyramidal

A

5

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10
Q

number of electron pairs: octahedral

A

6

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11
Q

linear bond angle

A

180

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12
Q

trigonal planar bond angle

A

120

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13
Q

tetrahedral bond angle

A

109.5

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14
Q

trigonal bipyramidal bond angle

A

90, 120 and 180

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15
Q

octahedral bond angle

A

90 and 180

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16
Q

lone pairs occupy

A

more space than bonding pairs

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17
Q

2 lone pairs, 2 bonds

A

bent

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18
Q

3 bond pairs, 1 lone pair

A

trigonal-pyramidal

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19
Q

2 bond pairs, 1 lone pair

A

V-shaped

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20
Q

Lewis Structures are useful for

A

electron counting and description of bonding

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21
Q

molecular shape considers that lone pairs

A

push actual atoms in certain ways

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22
Q

trigonal bipyramidal with one lone pair molecular shape

A

see-saw

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23
Q

octahedral with one lone pair molecular shape

A

square pyramid

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24
Q

octahedral with two lone pairs molecular shape

A

square planar

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25
Q

Molecular Orbital

A

orbital overlap

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26
Q

sigma bond

A

covalent bond for two electrons; elongated, ellipse shape

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27
Q

when a bond forms, energy is

A

released

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28
Q

sp3 hybrid orbitals are

A

tetrahedral

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29
Q

C-C bond is weaker than

A

C-H bond

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30
Q

structural isomers differ in

A

connectivity

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31
Q

isopropyl

A

-CH(CH3)2

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32
Q

tert-Butyl

A

-C(CH3)3

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33
Q

average bond order

A

bonds / # resonance structures

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34
Q

double and triple bonds in geometry only count as

A

one electron pair

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35
Q

formal charge (where valence electrons means from original atom)

A

valence electrons - # lone pair electrons - 1/2(# bonding electrons)

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36
Q

we number chain closest to

A

branch point

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37
Q

conformational isomers

A

differ due to bond rotation

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38
Q

bond rotation slows with

A

cooling

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39
Q

Newman Projection

A

looking down with carbons in a row

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40
Q

dihedral angle

A

angle between front and back hydrogen/group when looking at a molecule via Newman Projection

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41
Q

staggered

A

most stable conformation; hydrogens/groups as far apart as possible

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42
Q

eclipsed

A

least stable conformation; increase in potential energy

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43
Q

torsional strain

A

bonds-electron repulsion

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44
Q

in eclipsed conformation, there is more

A

torsional strain

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45
Q

antiperiplanar staggered

A

`most stable for butane; two methyl groups as far apart from each other as possible

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46
Q

gauche staggered

A

methyl groups at 60 degrees; steric strain

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47
Q

anticlinal eclipsed

A

eclipsed but methyl groups not close for butane

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48
Q

synperiplanar eclipsed

A

methyl groups as close as they can be to each other; steric and torsional strain

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49
Q

bigger substituents near each other,

A

higher energy (gauche/eclipsed)

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50
Q

to calculate conformer energy values,

A

add up gauche/eclipsed values between ALL groups (use table)

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51
Q

chiral

A

molecules that have a non-superimposable mirror image

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52
Q

stereoisomers

A

same numbers and types of atoms, differ in three-dimensional space

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53
Q

asymmetric carbon atom

A

stereogenic centre

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54
Q

enantiomers

A

pairs of non-superimposable mirror image molecules

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55
Q

racemate

A

1:1 mixture of enantiomers

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56
Q

in a 1:1 mixture of enantiomers, rotation of plane polarised light would be

A

zero

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57
Q

enantiomers rotate plane polarised light in

A

opposite directions

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58
Q

optically active

A

a compound that rotates plane polarised light

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59
Q

enantiomers have the same physical and chemical characteristics except

A

in their behaviour towards plane polarised light and their reactivity in a chiral environment

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60
Q

specific rotation [alpha]D

A

alpha/l x c

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61
Q

assigning absolute configuration about an asymmetric carbon

A

priority based on decreasing atomic number, viewing molecule along bond from asymmetric carbon to lowest priority

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62
Q

priority #1 atomic number is at

A

bottom

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63
Q

if clockwise, denoted as

A

R

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64
Q

if anticlockwise, denoted as

A

S

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65
Q

phantom atoms

A

if a carbon is double bonded to an atom, we treat it as a single bond to two of this atom

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66
Q

the more H atoms a carbon is bonded to,

A

the lower in priority

67
Q

number of stereoisomers

A

2^n, where n is number of asymmetric centres

68
Q

mirror images will have reversed

A

S and R

69
Q

diastereoisomers

A

stereoisomers that are not enantiomers

70
Q

S cancels

A

R

71
Q

meso compound

A

stereoisomer with two or more asymmetric carbon atoms that is NOT chiral

72
Q

ring strain

A

angle strain, torsional strain, steric strain

73
Q

highest ring strain energy

A

cyclopropane

74
Q

lowest ring strain energy

A

cyclohexane

75
Q

preferred cyclohexane conformation

A

chair

76
Q

all bonds in chair conformation are

A

staggered, so torsional strain is eliminated

77
Q

axial hydrogens

A

parallel to axis that goes through centre of ring vertically

78
Q

equatorial hydrogens

A

radiate out from equator of ring

79
Q

rings on cyclohexane should be in

A

equatorial position

80
Q

why should rings in cyclohexane be equatorial?

A

1,3-diaxial steric interaction

81
Q

groups on same face of cycloalkane

A

cis

82
Q

groups on different face of cycloalkane

A

trans

83
Q

groups remain cis or trans even when they

A

flip between axial and equatorial

84
Q

bigger group should be

A

equatorial

85
Q

ax-eq and eq-ax are identical if

A

the substituents are the same

86
Q

cis is higher in energy for fused cyclohexanes because

A

one carbon is axial

87
Q

you cannot ring flip

A

trans-decalin cyclohexane

88
Q

the more stable/conformationally rigid fused cyclohexane

A

trans-decalin

89
Q

hybridised orbital for trigonal planar/double bonds

A

sp^2

90
Q

hybridised orbital for tetrahedral

A

sp^3

91
Q

pi bond

A

bond between two carbon atoms where we’ve formed a sigma bond and we’re overlapping two p orbitals side-on

92
Q

pi region is

A

electron-rich

93
Q

in the pi region, electrons are not as

A

tightly held

94
Q

sigma bond is stronger than

A

pi bond

95
Q

no rotation about a

A

pi bond

96
Q

geometric isomers form due to to

A

inability of double carbon-carbon bonds to rotate

97
Q

we number chain giving the double/triple bond the

A

lowest number/top priority

98
Q

Z

A

of substituents of higher priority are on the same side of the double bond

99
Q

E

A

if substituents of higher priority are on different sides of the double bond

100
Q

which types of alkenes are less stable, cis or trans?

A

cis

101
Q

steric strain is present in

A

cis alkenes

102
Q

cumulated/allenes

A

consecutive double bonds

103
Q

conjugated

A

double-single-double

104
Q

isolated

A

double-single-single-single-etc.-double

105
Q

bonds with partial double bond character will be

A

shorter

106
Q

partial double bond character is present in

A

conjugated systems

107
Q

conjugated systems are

A

more stable

108
Q

benzene is comprised of a

A

continuous pi cloud circuit with partial double bond character throughout the entire loop

109
Q

resonance stabilisation

A

electrons are delocalised in pi cloud

110
Q

ortho/o

A

1,2

111
Q

meta/m

A

1,3

112
Q

para/p

A

1,4

113
Q

naming benzenes with more than two substituents

A

number substituents to give lowest possible numbers, list alphabetically

114
Q

when do we number benzenes according to the chain

A

if the chain attached to the benzene has more than six carbons

115
Q

constitutional isomer

A

same molecular formula, different structure

116
Q

double bonds are composed of

A

one sigma bond and one pi bond

117
Q

all atoms directly attached to double bond will be

A

coplanar

118
Q

aromatic compounds

A

planar, cyclic, conjugated, Huckel’s rule

119
Q

Huckel’s rule

A

4n + 2 pi electrons where n is a whole number

120
Q

sp hybridised

A

linear, triple bonds

121
Q

each sp bond contains

A

two pi bonds and one sigma bond

122
Q

primary carbon

A

carbon bonded to one carbon

123
Q

secondary carbon

A

carbon bonded to two carbons

124
Q

tertiary carbon

A

carbon bonded to three carbons

125
Q

quaternary carbon

A

carbon bonded to four carbon

126
Q

benzylic carbon

A

carbon directly attached to a carbon of a benzene ring (sp^3)

127
Q

aryl carbon

A

carbon part of benzene ring (sp^2)

128
Q

vinylic carbon

A

carbon that is part of a double bond (sp^2)

129
Q

allylic carbon

A

carbon bonded to a carbon-carbon double bond carbon (bonded to a vinylic carbon, sp^3)

130
Q

primary alcohol

A

hydroxyl carbon bonded to one other carbon

131
Q

secondary alcohol

A

hydroxyl carbon bonded to two other carbons

132
Q

tertiary alcohol

A

hydroxyl carbon bonded to three other atoms

133
Q

ether

A

oxygen atom bonded to two carbons

134
Q

ether nomenclature

A

add ether on the end with a space; alkyl groups are substituents

135
Q

thiol

A

sulphur bonded to carbon and hydrogen

136
Q

thiol nomenclature

A

add ‘thiol’ on end

137
Q

primary amine

A

N attached to one carbon

138
Q

secondary amine

A

N attached to two carbons

139
Q

tertiary amine

A

N attached to three carbons

140
Q

alcohol has priority over

A

amine group

141
Q

nitrogen has a lone pair which can be

A

donated in acid-base reactions

142
Q

C=O bond

A

sigma C-O bond, pi C-O bond

143
Q

carboxylic acids have priority over

A

alcohols and amines

144
Q

primary amide

A

N is attached to two hydrogens and C=O

145
Q

secondary amide

A

N is attached to one H, one R group and the C=O

146
Q

tertiary amide

A

C=O is attached to two R groups and the C=O

147
Q

nitriles

A

carbon-nitrogen triple bonds

148
Q

polar bonds arise from

A

electronegativity differences

149
Q

in polar bonds, partial positive charge is equal in magnitude to

A

partial negative charge

150
Q

dipole moment

A

degree of polarity

151
Q

dipole moment units

A

Debye (D)

152
Q

dipole moment points towards

A

negative end of whole molecule

153
Q

where there is symmetry/the negative ends cancel out, there will be

A

no net dipole moment

154
Q

cis and trans isomers can have different

A

polarities

155
Q

in the C=O atom, the pi bond/cloud is distorted towards the

A

O atom

156
Q

dispersion forces

A

due to instantaneous/temporary dipole forces

157
Q

attraction in dispersion forces is between

A

positive nucleus and negative electron cloud

158
Q

dispersion forces increase with

A

size of atom

159
Q

states of non-polar electron can be understood by the strength of

A

dispersion forces

160
Q

alkanes have strong

A

dispersion forces

161
Q

more branched molecules have weaker

A

dispersion forces

162
Q

lone pairs contribute to hydrogen bonding by providing

A

localised centres of negative charge

163
Q

if the oxygen is not attached to a hydrogen, it

A

cannot engage in hydrogen bonding

Chemistry 1 (4 decks)

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