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exam #2 Flashcards

1
Q

bond breaking always requires

A

energy

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2
Q

bond formation always

A

releases energy

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3
Q

types of arrows

A

rxn arrow
double rxn arrow
double-headed arrow
full-headed curved arrow
half-headed curved arrow (fish hook)

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4
Q

rxn arrow is drawn between

A

starting materials and products in an equation

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5
Q

double rxn arrows are drawn b/w the

A

starting materials and products in an equilibrium equation

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6
Q

double headed arrow

A

drawn between resonance structures

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7
Q

full-headed curved arrow shows

A

movement of electrons

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8
Q

half-headed curved arrow shows

A

movement of a single electron

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9
Q

bond dissociation energy is the

A

energy needed to homolytically cleave a covalent bond

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10
Q

energy absorbed or released by deltaH is

A

enthalpy change / heat of rxn

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11
Q

deltaH is positive…

A

energy is absorbed
rxn is endothermic

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12
Q

deltaH is negative

A

energy is released
rxn is exothermic

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13
Q

bond breaking is

A

ENDOthermic

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14
Q

bond making is

A

EXOthermic

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15
Q

comparing bond dissociation is equivalent to

A

comparing bond strength

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16
Q

stronger the bond,

A

higher its bond dissociation energy

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17
Q

bond disassociation energies decrease

A

down a column of the PT

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18
Q

generally, short bonds are

A

Stronger bonds

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19
Q

halogen size increases,

A

bond strength decreases

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20
Q

deltaH overall enthalpy change =

A

sum of deltaH bonds broken + sum of deltaH bonds formed

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21
Q

deltaH =

A

deltaH (broken bonds) - deltaH (formed bonds)

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22
Q

kinetics describes

A

reaction rates

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23
Q

equilibrium constant (Keq) relates

A

the amount of starting material and product at equilibrium

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24
Q

isomers are

A

have the same molecular formula but different placements

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25
Q

how do stereoisomers differ from constitutional isomers?

A

stereoisomers only differ in the way the atoms are oriented in space

  • identical IUPAC names
  • same functional groups
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26
Q

what is a three-dimensional arrangement is called

A

a configuration

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27
Q

stereoisomers differ in

A

configuration

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28
Q

what does achiral mean?

A

a molecule or object that is superimposable on its mirror image

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29
Q

what does chiral mean?

A

a molecule or object that is NOT superimposable on its mirror image

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30
Q

in 3D achiral configuration, the bonds and atoms (x)

A

align

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31
Q

achiral molecules usually contain a

A

plane of symmetry

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32
Q

chiral molecules do not have a

A

plane of symmetry

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33
Q
A
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34
Q

stereoisomers have

A

different 3D arrangement of atoms

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35
Q

two types of isomers

A

constitutional
stereoisomer

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36
Q

constitutional isomers differ

A

in the way atoms are connected to each other

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37
Q

constitutional isomers have

A

different IUPAC names
same/different functional groups
diff PHYSICAL and CHEMICAL properties

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38
Q

stereoisomers differ ONLY in the way

A

that the atoms are oriented in space

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39
Q

stereoisomers have identical

A

IUPAC names (differ with prefixes like cis or trans)

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40
Q

a particular 3D arrangement is a

A

configuration

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41
Q

constitutional isomers:

A

SAME molecular formula

DIFFERENT names

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42
Q

stereoisomers:

A

SAME molecular formula

SAME NAME except for the prefix

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43
Q

what does chiral mean

A

molecule or object that is NOT superimposable on its mirror image

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44
Q

socks are

A

superimposable on their mirror image so they are achiral

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45
Q

achiral

A

molecule or object that is superimposable on mirror image

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46
Q

how to test chirality

A

1) draw molecule in 3D
2) draw mirror image
3) align all bonds + atoms
4) to superimpose a molecule and its mirror image, you cannot break any bonds to perform any rotation

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47
Q

enantiomers are

A

not superimposable stereoisomers

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48
Q

a carbon atom bonded to four different groups is

A

a tetrahedral stereogenic center

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49
Q

most chiral molecules contain

A

one or more stereogenic centers

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50
Q

what is a stereogenic center?

A

site in a molecule at which the interchange of two groups forms a stereoisomer

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51
Q

a carbon atom w/ four different groups is a tetrahedral stereogenic center b/c…

A

interchange of two groups converts one enantiomer into another

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52
Q

a carbon atom bonded to four different groups is a

A

stereogenic center

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53
Q

with no stereogenic centers, a molecule is usually

A

NOT chiral

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54
Q

with one tetrahedral stereogenic center, a molecule is

A

ALWAYS chiral

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55
Q

with two or more stereogenic center, a molecule

A

MAY or MAY NOT be chiral

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56
Q

a plane of symmetry is a

A

mirror plane that cuts a molecule in half so that one half of the molecule is a reflection of the other half

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57
Q

achiral molecules usually contain a

A

plane of symmetry but chiral molecules do not

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58
Q

the presence of a plane symmetry makes a molecule

A

ACHIRAL

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59
Q

what C atoms cannot be a tetrahedral stereogenic center?

A

CH2 and CH3 groups (more than 1 H bonded to C)

any sp or sp2 hybridized C (less than 4 groups around C)

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60
Q

any molecule with one tetrahedral stereogenic center is a

A

chiral compound and exists as a pair of enantiomers

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61
Q

different ways of drawing an enantiomers?

A

1) drawing an enantiomers as a reflection

2) drawing an enantiomer by inverting the configuration of a stereogenic center

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62
Q

labels for stereogenic centers

A

R or S

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63
Q

R goes

A

clockwise

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64
Q

S goes

A

counterclockwise

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65
Q

you have to assign..

A

priority to label stereogenic center R or S

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66
Q

if two atoms on a stereogenic center are the same,

A

assign priority based on atomic number of the atoms bonded to these atoms

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67
Q

one atom of higher atomic number determines

A

higher priority

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68
Q

if two isotopes are bonded to the stereogenic center,

A

assign priorities in order of decreasing mass number

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69
Q

to assign a priority to an atom that is part of a multiple bond,

A

treat a multiply bonded atom as an equivalent number of singly bonded atoms

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70
Q

how do you assign R or S to a molecule when the lowest priority group is not oriented towards the back?

A

rotate and flip the molecule until the lowest priority molecule is in the back

assign R or S

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71
Q

in rotating a molecule about a single bond, the

A

rotation of three groups changes

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72
Q

in flipping a molecule 180 degrees,

A

the position of all four groups changes

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73
Q

for n stereogenic centers,

A

the max number of stereoisomers is 2^n

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74
Q

with one stereogenic center, there are always two stereoisomers which are

A

enantiomers

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75
Q

with two stereogenic centers, the

A

max number of stereoisomers is four

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76
Q

what must you NOT do when testing a compound’s superimposablility

A

DO NOT break any bonds

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77
Q

diastereomers are

A

stereoisomers that are NOT mirror images

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78
Q

enantiomers are

A

stereoisomers that are mirror images

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79
Q

a meso compound is an

A

achiral compound that contains tetrahedral stereogenic centers

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80
Q

do meso compounds have a plane of symmetry

A

YES

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81
Q

identical compounds have the same

A

R,S designations at every tetrahedral stereogenic center

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82
Q

enantiomers have exactly opposite

A

R,S designations

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83
Q

diastereomers have the same

A

R,S designation for at least one stereogenic center

and the opposite for at least one of the other stereogenic centers

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84
Q

if a compound has two stereogenic centers w/ the R configuration…

A

enantiomers is S,S

diastereomers are either R,S or S,R

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85
Q

chemical and physical ppties of two enantiomers are

A

IDENTICAL except in their interaction w/ chiral substances

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86
Q

two enantiomers have identical

A

physical properties (melting pt, boiling pt, solubility)

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87
Q

plane polarized light is

A

ordinary light consists of electromagnetic waves that oscillate in all plans perpendicular to the direction in which the light travels

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88
Q

passing light through a polarizer allows light in one

A

one plane to come through resulting in plane-polarized light (aka polarized light)

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89
Q

plane polarized light has an

A

electric vector that oscillates in a single plane

90
Q

a polarimeter is an

A

instrument that allows plane-polarized light to travel through a sample tube containing an organic compounds

91
Q

after the light exits the sample tube, an analyzer slit is

A

rotated to determine the direction of the plane of the existing polarized light

92
Q

with achiral compounds, the light exists the sample tube

A

UNCHANGED

93
Q

plane of polarized light is in the same

A

position it was before entering the sample tube

94
Q

a compound that does not change the plane of

A

polarized light is said to be optically inactive

95
Q

with chiral compounds, the plane of the polarized light is

A

rotated through an angle

96
Q

the angle is measured in

A

degrees (observed rotation)

97
Q

compound that rotates plane of polarized light

A

OPTICALLY ACTIVE

98
Q

rotation of polarized light can be in the

A

clockwise or counterclockwise direction

99
Q

dextrorotatory means

A

when rotation is clockwise (d)

100
Q

levorotatory means

A

when rotation is counterclockwise (l)

101
Q

two enantiomers rotate

A

plane-polarized light to an equal extent but in the opposite direction

102
Q

racemic mixtures is

A

an equal amount of two enantiomers (optically INACTIVE)

103
Q

what is the observed rotation of an equal amount of two enantiomers?

A

two enantiomers rotate plane-polarized light to an equal extent but in opp directions and rotations cancel

104
Q

specific rotation is defined using

A

a specific sample tube length (~1 dm), concentration, temp (25 C), wavelength (589 nm)

105
Q

enantiomeric excess (ee) is

A

how much more there is of one enantiomers (aka optical purity)

106
Q

ee =

A

% of one enantiomer - % of the other enantiomer

107
Q

ee tells how much

A

one enantiomers is present in excess of racemic mixture

108
Q

physical properties of diastereomers

A

different including optical rotation

109
Q

chemical properties of enantiomers

A

two enantiomers have exactly the same chem ppties except for their rxn with chiral, non-racemic reagents

110
Q

what’s the reagent?

A

chemical susbtance with which an organic compound reacts (sometimes drawn on left side of equation w/ other reactants)

111
Q

kinds of organic reactions?

A

substitution, elimination, addition

112
Q

substitution is a reaction where

A

an atom or group of atoms is replaced by another atom or group of atoms

113
Q

in a general substitution rxn,

A

Y replaces Z on a carbon atom

114
Q

substitution rxns involve

A

sigma bonds

one sigma bond break and another forms at the same carbon atom

115
Q

elimination is a reaction in which

A

elements of the starting material are “lost” and a pi bond is formed

116
Q

in an elimination rxn,

A

two groups X and Y are removed from a starting material

117
Q

what bonds are broken in an elimination rxn?

A

two sigma bonds are broken

pi bond is formed b/w adjacent atoms

118
Q

most common examples of elimination ocur when

A

X = H and Y is a heteroatom more electronegative than carbon

119
Q

addition is a reaction where

A

elements are added to a starting material

120
Q

in an addition reaction,

A

new grous X and Y are added to a starting material

121
Q

what bonds are broken/formed in an addition reaction?

A

pi bond is broken

two sigma bonds are formed

122
Q

addition and elimination rxns are

A

OPPOSITES

a pi bond is formed in eliminiation rxns

pi bond is formed in addition rxns

123
Q

to determine whether a reaction is a substitution, elimination or addition w/ a complex starting material,

A

concentrate on the functional groups that CHANGE

124
Q

reaction mechanism is a

A

detailed description of how bonds are broken and formed as a starting material is converted to a product

125
Q

a reaction mechanism describes the

A

relative order and the rate of bond cleavage and formation

126
Q

one step rxn is called a

A

concerted rxn

no matter how many bonds are broken or formed, a starting material is converted directly to a product

127
Q

a stepwise rxn involves

A

more than one step

starting material is first converted to an unstable intermediate then forms the product

128
Q

reactive intermediate

A

unstable intermediate which goes on to form the product

129
Q

when a bond is broken…

A

the electrons in the bond can be divided equally or unequally b/w the two atoms of the bond

130
Q

homolysis or homolytic cleavage

A

breaking bond by equally dividing the electrons b/w the two atoms in the bond

131
Q

heterolysis or heterolytic cleavage

A

breaking a bond by unequally dividing the electrons b/w the two atoms in the bond

132
Q

homolysis and heterolysis require

A

energy

both processes generate reactive intermediates

133
Q

homolysis generates

A

uncharged reactive intermediates w/ unpaired electrons

134
Q

heterolysis generates

A

charged intermediates

135
Q

ionic intermediates are seen in

A

polar reactions

136
Q

radical are

A

intermediates in radical reactions

137
Q

homolysis of the C-Z bond generates

A

two uncharged products w/ unpaired electrons

138
Q

reactive intermediates with a

A

single unpaired electron is called a radical

139
Q

most radicals are highly unstable because

A

they contain an atom that does not have an octet of electrons

140
Q

radicals typically have no

A

CHARGE

141
Q

radical reactions

A

intermediates in a group of rxns

142
Q

heterolysis of the C-Z bond can generate a

A

carbocation or a carboanion

143
Q

giving two electrons to Z and none to carbon generates

A

a positive charged carbon intermediates called a carbocation

144
Q

giving two electrons to C and none to Z generates

A

a negative charged carbon species called a carbanion

145
Q

both carbocations and carbanions are

A

unstable reactive intermediates

146
Q

carbocation contains a

A

carbon atom w/ 6 electrons

147
Q

carbanion has a negative charge on

A

carbon which is not very electronegative

148
Q

carbocations are

A

electrophiles

149
Q

carbanions are

A

nucleophiles

150
Q

carbocations and carbanions can be

A

intermediates in polar reactions (reactions in which a nucleophile reacts w/ an electrophile)

151
Q

homolysis and heterolysis generates

A

radicals, carbocations, carbanions (3 most reactive intermediates in orgo)

152
Q

radical with carbon

A

surrounded by 7 electrons

153
Q

carbocation w/ C

A

surrounded by 6 electrons

154
Q

carbanion w/ C

A

lone pair

155
Q

radical and carbocations are

A

electrophiles b/c they contain a carbon with no octet

156
Q

carbanions are

A

nucleophiles b/c they contain a carbon with a lone pair

157
Q

two radical can each donate

A

one electron to form a two electron bond

158
Q

bond formation always

A

releases energy

159
Q

two ions with unlike charges can

A

come together with the negatively charged ion donating both electrons to form the two-electron bond

160
Q

bond dissociation energy is the

A

energy needed to homolytically cleave a covalent bond

161
Q

enthalpy or heat of reaction

A

energy absorbed or released in any rxn

162
Q

because bon breaking requires energy…

A

bond dissociation energies are always POSITIVE

163
Q

homolysis is always

A

endothermic

164
Q

bond formation always

A

releases energy (exothermic)

165
Q

comparing bond dissociation energies is equivalent to

A

comparing bond strength

166
Q

stronger the bond,

A

higher its bond dissociation energy

167
Q

bond dissociation energies decrease

A

down a column of the PT

168
Q

shorter bonds are

A

stronger bonds

169
Q

overall enthalpy change =

A

sum of bonds broken - (-) sum of bonds formed

170
Q

when deltaH is positive,

A

more energy is needed to break bond than is released in forming bonds

171
Q

bonds broken in the starting material are

A

stronger than bonds formed in the product

172
Q

when deltaH is negative,

A

more energy is released in forming bonds than is needed to break bonds

173
Q

bonds formed in the product are stronger than

A

the bonds broken in the starting mateiral

174
Q

thermodynamics describe how

A

the energies of reactants and products compare and what the relative amounts of reactants/products are at equilibrium

175
Q

kinetics describes

A

reaction rates

176
Q

the equilibrium constant, Keq, is a

A

mathematical expression that relates the amount of starting material and product at eqilibrium

177
Q

when Keq > 1

A

equilibrium favors products and eq lies to the RIGHT

178
Q

when Keq < 1

A

eq favors starting materials and lies to the LEFT

179
Q

for reaction to be useful, eq must favor the

A

products

so Keq > 1

180
Q

equilibrium always favors the species

A

lower in energy

181
Q

when Keq > 1,

A

Keq is positive

deltaG is negative

energy released

182
Q

when Keq < 1,

A

Keq is negative

deltaG is positive

energy is absorbed

183
Q

compounds that are lower in energy have

A

increased stability

184
Q

because deltaG depends on the logarithim of Keq,

A

a small change in energy corresponds to a large difference in the relative amount of starting material + product at equilibrium

185
Q

delta G depends on

A

delta H and the entropy change delta S

186
Q

entropy change (delta S) is a measure of

A

the randomness in a system

more disorder, higher entropy

187
Q

deltaS is (+) when the products are

A

more disordered than the reactants

188
Q

deltaS is (-) when the products are

A

less disordered than the reactants

189
Q

reactions resulting in increased entropy

A

are favored

190
Q

delta G =

A

delta H - T (delta S)

191
Q

energy of activation is the minimum

A

amount of energy needed to break the bonds in the reactants

192
Q

larger activation energy,

A

greater the amount of energy that is needed to break bonds and slow the rxn rate

193
Q

structure of transition state is somewhere between the

A

structures of the starting material and product

194
Q

any bond that is partially formed or broken is drawn with a

A

dashed line

195
Q

any atoms that gains or loses a charge contains a

A

partial charge in the transition state

196
Q

transition states are drawn in

A

brackets with a superscript double dagger

197
Q

for a 2-step rxn,

A

an energy diagram must be drawn
two E diagrams combin to form a diagram for the overall 2step rxn
each step has its own energy barrier with a transition state at the energy max

198
Q

where are transition states located?

A

at energy maxima

199
Q

reactive intermediate B+ is located at

A

an energy minimum

200
Q

the step with the higher energy transition state is the

A

rate-determining step

201
Q

kinetics is the

A

study of reaction rates

202
Q

activation energy is the energy barrier that must be

A

exceeded for reactants to be converted to products

203
Q

higher concentration =

A

faster rate

204
Q

higher temperature =

A

faster rate

205
Q

delta G, delta H, delta K do not determine

A

the rate of a rxn

206
Q

delta G/H/K indicate the

A

direction of the equilibrium and the relative energy of reactants and products

207
Q

a rate law/rate equation shows

A

the relationship b/w the rxn rate and the concentration of the reactants (experimentally determined)

208
Q

fast reactions have

A

large rate constants

209
Q

slow reactions have

A

small rate constants

210
Q

rate constant (k) and activation energy are

A

inversely related

211
Q

high activation energy corresponds to a

A

small k (rate constant)

212
Q

rate equation contains concentration terms for

A

ALL reactants in ONE step mechanism

213
Q

rate equation contains concentration terms for only the

A

reactants involved in the rate-determining step in a multi-step rxn

214
Q

order of a rate equation =

A

sum of the exponents of the concentration terms in the rate equation

215
Q

order of a rate equation =

A

sum of the exponents of the concentration terms in the rate equation

216
Q

a two step rxn has a slow

A

rate-determining step and a fast step

217
Q

in a multi step mechanism, the reaction can occur

A

no faster than its rate-determining step

218
Q

only the concentration of the reactants in the

A

rate determining step appears in the rate equation

219
Q

a catalyst is a

A

substance that speeds up the rate of a reaction

  • recovered unchanged in a rxn, does not appear in the product
220
Q

uncatalyzed rxn has a

A

larger activation energy, slower rxn

221
Q

catalyzed rxn has a

A

lower activation energy, faster rxn

222
Q
A

orgo (6 decks)

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