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PSU Sophomore > Chem 210 Final > Flashcards

Chem 210 Final Flashcards

1
Q

As pka decreases, acidity

A

increases

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2
Q

A stronger acid, conj base …

A

weaker and more stable

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3
Q

Formal charge=

A

VE - (#of bond lines and individual LP e)

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4
Q

Octet rule

A

Atoms prefer to have 8 electrons in valence shell

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5
Q

Thermodynamics

A

predicts the most energetically stable product

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6
Q

Kinetics

A

determines what product will form the fastest

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7
Q

The e rich reactant uses its ___ in a reaction

A

HOMO electrons

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8
Q

electrons can move to ___ in response

A

sp2 and neighboring double bond

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9
Q

Unsaturated bond

A

double/triple bond

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10
Q

saturated

A

single bond

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11
Q

Polar covalent bonds

A

C-O
C-Br
C-N
C-Cl
O-H

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12
Q

Nonpolar covalent bonds

A

C-C
C-H

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13
Q

HONC

A

1 2 3 4 (bonds)

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14
Q

sp

A

linear

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15
Q

sp2

A

trigonal planar

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16
Q

sp3

A

tetrahedral

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17
Q

pi electrons cannot move to a

A

sp3 atom

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18
Q

prop

A

3

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19
Q

but

A

4

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20
Q

pent

A

5

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21
Q

hex

A

6

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22
Q

hept

A

7

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23
Q

oct

A

8

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24
Q

non

A

9

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25
Q

substituent-_____

A

substituent-parent-suffix

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26
Q

Alkene/alkyne always in ___

A

suffix

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27
Q

Resonance must maintain

A

conservation of charge

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28
Q

Best forms of resonance have

A

neutral atoms (or minimum charge), does not violate octet, never move e towards sp3 atom

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29
Q

EDG- e poor

A

Stabilizing

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30
Q

EDG - e-rich

A

Destabilizing

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31
Q

EWG e poor

A

Destabilizing

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32
Q

EWG e rich

A

Stabilizing

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33
Q

Electrophile

A

e poor, LUMO, full positive charge

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34
Q

Nucleophile

A

e rich, HOMO, full negative charge

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35
Q

To have a geometric isomer, a molecule needs

A

alkane

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36
Q

To have an enantiomer, a molecule needs

A

1 chiral center

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37
Q

To have a diastereomer, a molecule needs

A

2 chiral centers

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38
Q

Good LG

A

Weak base

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39
Q

ARIO

A

Atom
Resonance
Induction
Orbital

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40
Q

Explain atom in ARIO

A

Higher electronegativity -> better acid

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41
Q

Explain resonance in ARIO

A

More resonance, better acid

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42
Q

Explain orbital in ARIO

A

sp better than sp2 or sp3

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43
Q

Explain induction in ARIO

A

EWG stabilize - charge, EDG destabilize - charge

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44
Q

Constitutional isomer

A

same mf, diff connectivity

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45
Q

Enantiomers

A

Diff shape and spatial location
Mirror image (both change)

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46
Q

Diastereomer

A

Not mirror image (1 change)
at least 2 chiral centers

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47
Q

Alkene diastereomer

A

Highest priority groups on same side of alkene, (Z)

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48
Q

Higher priority group

A

higher atomic number

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49
Q

Acid catalysts make electrophilic atoms better

A

electrophiles

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50
Q

Bases make nucleophilic atoms better

A

nucleophiles

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51
Q

Acidic conditions form

A

positively charged intermediates

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52
Q

Basic conditions form

A

negatively charged intermediates

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53
Q

Acid/base rxns

A

proton transfer

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54
Q

Electrophile/nucleophile rnx

A

nucleophilic attack

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55
Q

Higher pka side is

A

favored

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56
Q

Higher LUMO, less

A

reactivity

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57
Q

Acids are electron

A

poor

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58
Q

Bases are electron

A

rich

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59
Q

Best LG, lowest

A

pkah

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60
Q

Oxidants

A

Cro3

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61
Q

Reductants

A

LiAlH4, NaBH4

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62
Q

Low energy base to high energy base

A

endothermic

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63
Q

SN1 will use H20, but

A

SN2 will not

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64
Q

Anion

A

negative charge

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65
Q

Cation

A

positive charge

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66
Q

tertiary cannot undergo

A

SN2

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67
Q

3 main reaction categories

A

Addition, substitution, elimination

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68
Q

When a molecule with a good LG interacts with a base,

A

elimination occurs

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69
Q

In order for elim to work, there must be a neighboring

A

H to protonate to form the pi bond and push out the LG

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70
Q

pka favors formation of

A

weaker acid

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71
Q

Good nuc, high

A

pkaH

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72
Q

Common acid catalysts

A

H2SO4
H3PO4
HCl

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73
Q

Common bases

A

NaOH, NaH, RMgBr

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74
Q

Nucleophiles

A

NaCN, NaN3, NaBH4, LiALH4

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75
Q

Bimolecular

A

SN2 and E2

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76
Q

Unimolecular

A

SN1 and E1

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77
Q

SN1 and E1 form

A

carbocation intermediate

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78
Q

Polar protic solvents

A

H20
methanol
ethanol
acetic acid

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79
Q

Polar aprotic solvents

A

acetone
DMSO
DMF
acetonitrile

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80
Q

Polar aprotic reaction

A

SN2 or E2

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81
Q

Polar protic reaction

A

SN1 or E1

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82
Q

SN1 reactions form

A

racemic mixture 50/50

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83
Q

Consider _____ of electrophile

A

LUMO

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84
Q

Consider ____ of nuc

A

HOMO

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85
Q

PCC

A

1 alc -> Aldehyde
2 alc -> Ketone

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86
Q

KMnO4

A

1 alc -> carboxylic acid
2 alc -> ketone

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87
Q

CrO3

A

1 alc-> carboxylic acid
2 alc -> ketone
3 alc -> NO RXN

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88
Q

H2 (lindlar)

A

alkyne to cis alkene

89
Q

H2 (PD/C)

A

alkyne to alkane

90
Q

LiAlH4

A

aldehyde -> 1 alc
ketone -> 2 alc
amide -> amine

91
Q

NaBH4

A

Aldehyde -> 1 alc
Ketone -> 2 alc

92
Q

Wedge up, dash

A

down

93
Q

Wedge right, dash

A

left

94
Q

Eclipsed conformation is least

A

stable and highest energy

95
Q

Anti-staggered conformation is

A

most stable bc 180 apart

96
Q

Most stable alkene

A

Most substituted (tetra)

97
Q

cis

A

Z

98
Q

trans

A

E

99
Q

H and LG need to be in the same

A

plane for E2 to work and both must be axial

100
Q

Axial

A

up or down

101
Q

Equatorial

A

left or right

102
Q

SN2 cannot do

A

3 carbon

103
Q

Any 1 alkyl halide,

A

SN2 major

104
Q

Only ever base

A

NaH and KoTbut

105
Q

H on wedge cannot be

A

elim

106
Q

Oxidants perform

A

oxidation

107
Q

Oxidants are

A

reduced

108
Q

Reductants perform

A

reduction

109
Q

Reductants are

A

oxidized

110
Q

sp hybridized atom has a total of ___ electron domains

A

2

111
Q

True or false: Resonance movement can occur in a saturated molecule

A

false

112
Q

True or false: A good leaving group is also a stable conjugate base

A

True

113
Q

The pka of an acid is ________ the pkaH of its conjugate base

A

equal to

114
Q

The ______ the conjugate base, the more stable the conjugate base

A

weaker

115
Q

The ________ the pka-H, the weaker the conjugate base

A

lower

116
Q

Consider the nucleophile’s

A

HOMO

117
Q

Consider the electrophile’s

A

LUMO

118
Q

A nucleophilic reactant _____ be incorporated into the structure of the product

A

will

119
Q

A base (sometimes/always) deprotonates a proton from a molecule

A

always

120
Q

An acid makes a molecule a more reactive

A

electrophile

121
Q

A strong base has a ________ pkaH

A

high

122
Q

A proton bonded to an atom that has more s character is

A

more acidic

123
Q

An atom with a higher electronegativity will typically have a ________ nucleophilicity due to a _______ _________

A

lower, lower, HOMO

124
Q

A low pka corresponds to a ____ acid

A

strong

125
Q

Strong acids and bases have a _______ potential energy

A

high

126
Q

A nucleophile uses its LP electrons to attack electrophiles. Electrophiles are attacked in their

A

LUMO

127
Q

Constitutional isomers

A

Same molecular formula, different connectivity of atoms

128
Q

Stereoisomers

A

Same connectivity but different spatial arrangement (enantiomers or diastereomers)

129
Q

Enantiomers

A

Non-superimposable mirror images (Hands)
Identical physical properties

130
Q

Diastereomers

A

Not mirror images
2 chiral centers

131
Q

Chiral center

A

A carbon atom bonded to four different groups

132
Q

sp2 atoms typically draw electrons

A

to themselves

133
Q

sp3 atoms typically give

A

give away electrons

134
Q

electron rich regions

A

negatively charged O, sp3 atom

135
Q

electron poor regions

A

pi/weak bonds, positive charges, sp2 atoms

136
Q

Broad peaks typically indicate

A

O-H (hydrogen bonding)

137
Q

Double bonds usually give what signals

A

strong, sharp

138
Q

EWG

A

Pull e density away from a molecule
Typically, electroneg atoms or groups with pi-accepting characterisitics
Stabilizing negative charges
Increase acidity by stabilizing the conjugate base

139
Q

Common EWG’s

A

NO2
CN
CF3
C=O

140
Q

EDG

A

Donate e density through resonance or induction
Often groups with LP or alkyl chains
Stabilize positive charges or e-deficient systems
Decrease acidity by destabilizing the conjugate base

141
Q

Common EDGs

A

OH
OR
NH2
R (alkyl groups)

142
Q

Elimination pi bonds

A

increase

143
Q

Addition pi bonds

A

Decrease

144
Q

A molecule that takes up more space will be a better

A

acid

145
Q

Most basic molecule will NOT have

A

resonance

146
Q

Most nucleophile will have a charge

A

negative

147
Q

GOOD LG, high

A

pkaH

148
Q

A favored reaction will have the pkaH of the LG ________ than the pkaH of the base

A

lower

149
Q

Smaller pkaH, stronger

A

base

150
Q

OTS pkaH

A

-1

151
Q

2^n =

A

of possible stereoisomers
n= # of chiral centers

152
Q

Lower pka= acid

A

Stronger acid (more likely to donate protons)

153
Q

Lower pkaH= conjugate acid

A

Stronger conjugate acid (more likely to donate protons)

154
Q

Low pkaH = base

A

Stronger base

155
Q

Strong acid —> conjugate base

A

weak

156
Q

Low pkaH = conjugate acid

A

Strong

157
Q

Acid donates

A

protons

158
Q

Base accepts

A

protons

159
Q

Electrophile is charged

A

positive

160
Q

Nucleophile is charged

A

negative

161
Q

Electron pushing arrows etiquette

A

Originate from lone pair or middle of bond
Never from H

162
Q

Antistaggered

A

Largest groups are 180 apart. most stable conformation

163
Q

Gauche staggered

A

Largest groups are 60 apart. Less stable due to steric strain

164
Q

Eclipsed

A

All groups aligned, highest energy due to torsional strain

165
Q

A hydrogen or substituent must be anti-periplanar to a LG for

A

E2 reaction to occur

166
Q

Anti-periplanar

A

Groups are in the same place but opposite sides of the bond axis (180)

167
Q

For SN2 reactions, primary substrates and strong nucleophiles favor a

A

single-step (NaOH, NaCN)

168
Q

For SN1 reactions, tertiary substrates stabilize the

A

carbocation intermediate, so weak nucleophiles work well (H20, ROH)

169
Q

Primary carbons favor a ________ attack, but tertiary favor _____

A

backside, carbocation formation

170
Q

Polar aprotic

A

DMSO
Acetone
DMF

171
Q

Polar protic

A

H20
Alcohols

172
Q

Polar aprotic solvents cause

A

SN2 and E2

173
Q

Polar protic solvents cause

A

E1 and SN1

174
Q

SN1 will cause a mixture

A

racemic

175
Q

E2 eliminations favor

A

strong bases and crowded alkyl halides

176
Q

E1 elims prefer

A

weak bases with tertiary substrates, forming a carbocation intermediate

177
Q

KOtBu as a base typically yields (elimination)

A

less-substituted alkene

178
Q

NaOH or NaOEt often yields (elimination)

A

more substituted alkene

179
Q

Tosylation coverts OH into

A

OTS, which is a better LG than OH

180
Q

NaBH4 is generally used for

A

ketones and aldehydes only

181
Q

LiAlH4 is generally used for

A

carboxylic acids, esters, ketones, and aldehydes

182
Q

PCC

A

stops at aldehydes for 1 alc

183
Q

CrO3 or H2CrO4 can form

A

carboxylic acids from 1 alc

184
Q

Secondary alcohols oxidize to

A

ketones

185
Q

Hydrogenation of alkenes and alkynes

A

Alkenes/alkynes are reduced to alkanes (or alkenes)

186
Q

H2 with Pd/Pt reduces alkenes or alkynes to

A

alkanes

187
Q

H2 with Lindlar or Li/NH3 reduce alkynes to

A

cis alkene, trans alkene

188
Q

O3/Zn splits alkenes to form

A

aldehydes/ketones

189
Q

KMnO4 fully oxidizes alkenes to

A

carboxylic acids

190
Q

OH is added to the _______ alkene in markovnikov hydration of alkenes

A

most-substituted carbon

191
Q

OH is added to the _______ alkene in anti-markovnikov hydration of alkenes

A

less-substituted carbon (typically cis)

192
Q

Bromination of alkenes

A

Each double bonded carbon gains one bromine atom

193
Q

Downfield

A

ppm increases, deshielded protons (near electroneg atoms or pi-systems)

194
Q

Upfield

A

ppm decreases, shielded protons (far from electroneg groups)

195
Q

N+1 rule to find splitting group

A

n= number of equivalent neighboring protons

196
Q

Singlet splitting pattern

A

0 neighbors

197
Q

Doublet splitting pattern

A

1 neighbor

198
Q

Triplet splitting pattern

A

2 neighbors

199
Q

Quartet splitting pattern

A

3 neighbors

200
Q

Nieghboring non-equivalent protons

A

split each other’s signals

201
Q

Protons attached to the same atom

A

do not split each other

202
Q

Oxidation #

A

increases when oxidation

203
Q

Oxidation # decreases when

A

reduction

204
Q

Reduction is the same as

A

addition and hydration

205
Q

Oxidation is the same as

A

elimination and dehydration

206
Q

A tri-sub alkene is ______ stable than a mono-sub alkene

A

more

207
Q

Bulky groups on chair cyclohexanes prefer to be on _______ bonds

A

equatorial

208
Q

Tertiary cannot undergo

A

SN2

209
Q

NaCN only functions asa

A

nucleophile

210
Q

The LG and H should be _______ on chair cyclohexane

A

both be axial

211
Q

Stereocenters that undergo SN2 will ______ its stereochemical configuration

A

invert

212
Q

In an E2 reaction, the major product orients the bulkiest group trans (true/false)

A

true

213
Q

The LG and H must be

A

anti for E2 to perform

214
Q

Tertiary and 2 alkyl bromide can readily undergo

A

E2

215
Q

An anion with large steric bulk cannot function as a

A

nucleophile

216
Q

An oxidant ______ an organic compound

A

oxidizes

217
Q

An oxidant is _____ in an organic reaction

A

reduced

218
Q

CrO3 will react with

A

1 alc and 2 alc, NOT 3 alc

PSU Sophomore (3 decks)

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