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MCAT 1 > Orgo I > Flashcards

Orgo I Flashcards

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MCAT flashcards
1
Q

aromatic

A

alternating single and double bonds

delocalized pi conjugated system

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2
Q

nitrile

A

cyano

Carbon triple bonded to nitrogen

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3
Q

Formal charge

A

The difference between the number of electrons in an atom’s valence shell in its ground state and the number assigned

valence electrons- bonds- nonbonded electrons

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4
Q

epoxide

A

cyclic ether with a 3-atom ring

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5
Q

what are the steps of alcohol dehydration

A

protonation of an alcohol with water, water leaves and forms a carbocation, OH- attacks carbocation and forms alkene

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6
Q

Conformational isomers

A

when a molecule twists or rotates around its bond
known as a conformer
NOT TRUE ISOMERS- SAME exact molecule

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7
Q

enamine

A

secondary amine condensed with alkene

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8
Q

How can an alcohol form an alkene?

A

dehydration

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9
Q

ester

A

derived from an acid with hydroxyl replaced by an alkoxy group

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10
Q

Observed rotation

A

degree to which a sample rotates plane polarized light

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11
Q

What characteristics make up an Sn2 reaction

A

substitution, bimolecular

reaction rate depends of the concentration of two species

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12
Q

donor molecule

A

lewis base

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13
Q

Bases

A

abstract protons

full or partial negative charge

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14
Q

ketal

A

central carbon bonded to two -OR groups, two R groups

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15
Q

sp3d2

A

octahedral
square pyramidal
square planar
90°

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16
Q

meso compounds

A

molecules with two or more chiral centers that contain a plane of symmetry

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17
Q

epimers

A

differ only at one chiral center

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18
Q

by what mechanism is a 1° alcohol dehydrated?

A

E2

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19
Q

E/Z convention

A

Prioritize the two constituents on each carbon by molecular weight
E- two higher priority on opposite sides of the double bond
Z- two higher priority on the same side of the double bond

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20
Q

electrophiles

A

electron poor

partial or full positive charge

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21
Q

rotation of plane-polarized light

A

enantiomers rotate plane-polarized light

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22
Q

a triple bond has

A

one sigma and two pi bonds

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23
Q

heat of combustion

A

total energy released as heat when a substance undergoes complete combustion with oxygen under standard conditions

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24
Q

Huckel’s Rule

A

aromatic compounds must have exactly 4n+2 pi electrons

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25
Q

hydroxyl

A

-OH

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26
Q

polarimeter

A

apparatus that measures the rotation of plane-polarized light as it passes through a sample

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27
Q

racemic mixture

A

optically inactive mixture with 50:50 ratio of R:S

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28
Q

Do enantiomers contain a chiral center?

A

Yes

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29
Q

How many steps are in an Sn1 reaction?

A

two

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30
Q

what molecules does an Sn1 reaction favor?

A

poor nucleophiles, 3° carbons, polar protic solvents

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31
Q

are alcohols electro or nucleophilic?

A

nucleophilic

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32
Q

leaving groups

A

atoms or molecules that leave the parent molecule during a reaction

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33
Q

Relative configuration

A

spatial arrangement is identical but one non-identical substituent

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34
Q

-Ar is

A

benzene

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35
Q

Geometric isomers

A

cis/trans

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36
Q

Hybridization

A

mixing of atomic orbitals into new ones with different energies, shapes, etc suitable for the pairing of electrons to form chemical bonds

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37
Q

imine

A

contains a carbon nitrogen double bond

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38
Q

alcohol

A

organic compound with an -OH group

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39
Q

What characteristics make up an E1 reaction

A

elimination, unimolecular

reaction rate depends on the concentration of the reactant only

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40
Q

are meso compounds optically active?

A

no

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41
Q

nucleophiles

A

attach carbons and central atoms

full or partial negative charge

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42
Q

a single bond has

A

one sigma bond

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43
Q

Is alkane synthesis syn or anti addition?

A

syn

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44
Q

nitro

A

NO2

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45
Q

Acetyl

A

methyl group single bonded to a carbonyl

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46
Q

are nucleophiles a function of thermodynamics or kinetics?

A

kinetics

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47
Q

Do alcohols have a higher or lower BP/MP than alkanes? why?

A

higher, hydrogen bonding

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48
Q

How can the opening of an epoxide ring occur?

A

Sn1- protonation of O, opening of ring as the nucleophile attacks carbon, base abstracts proton

Sn2- nucleophile attacks carbon as the ring opens and the oxygen is protonated

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49
Q

Syn addition

A

two new bonds formed on the same side

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50
Q

Electronegativity of O

A

2.5

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51
Q

Pi bond

A

formed by side to side overlap of two p orbitals

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52
Q

what conformation of cyclohexane has zero ring strain

A

chair conformation

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53
Q

VESPR

A

Predicts the shape molecules will take due to the repulsion of lone pairs of electrons

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54
Q

grignard

A

R-MgBr

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55
Q

bond strength

A

measures of the energy required to completely break two atoms apart

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56
Q

what molecules does an E1 reaction favor?

A

weak bases, 3° carbons, polar protic solvents

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57
Q

Resonance

A

structures that are two forms of a molecule where the chemical connectivity is the same but the electrons are distributed differently around the structure

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58
Q

alkoxy

A

alkyl group single bonded to oxygen

R-O

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59
Q

How do R and S differ in the ways that they rotate plane polarized light?

A

same degree, opposite directions

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60
Q

MOM

A

methoxy-methyl ether

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61
Q

step 1 of an E2 reaction

A

abstraction of a proton by a base with the collapse of the electrons to an alkene and ejection of the leaving group

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62
Q

benzyl

A

benzene attached to a carbon

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63
Q

recipient molecule

A

lewis acid

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64
Q

protection of alcohols can be achieved with what?

A 
trimethylsilyl ether (TMS) 
methoxy-methyl ether (MOM)
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65
Q

what direction to electrons flow?

A

negative to positive charge

bases/nucleophiles attach electrophiles

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66
Q

isomers

A

two molecules that have the same molecular formula but are different compounds

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67
Q

hydrazine

A

H2N-NH2

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68
Q

aliphatic

A

carbons form open chains

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69
Q

what are the products and reactants in a grignard synthesis?

A

carbonyl and grignard form an alcohol

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70
Q

vertical lines on a fischer projection

A

into the page

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71
Q

hemiacetal

A

acetal with one -OR group replaced with -OH

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72
Q

anomeric carbon

A

c-OH next to the oxygen of a ring

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73
Q

what alkanes have the highest melting points

A

straight chain

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74
Q

Dipole Moment

A

any time charge is not evenly distributed within a bond (nonequal electronegativities)

75
Q

sp3d

A 
trigonal bipyramidal 
seesaw
T-shape
Linear
120° and 90°
76
Q

how can protecting groups be removed?

A

acidification

77
Q

ether

A

r-o-r

78
Q

aldehyde

A

organic compound containing formyl

79
Q

Vinyl

A

ethylene with one H replaced by another atom (halogen)

80
Q

mesyl

A

salt/ester of methanesulfuric acid H3C-SO3

81
Q

anhydride

A

two acyl groups bonded to the same oxygen

82
Q

Maximum optically active stereoisomers

A

2^n

n- number of chiral centers

83
Q

Amine

A

derived from ammonia with hydrogen replaces by an organic group

84
Q

How many steps are in an E1 reaction?

A

two

85
Q

How can an alcohol be formed from a ketone or aldehyde?

A

reduce

86
Q

acetal

A

central carbon bonded to two -OR groups, one R group and a hydrogen

87
Q

step 1 of an E1 reaction

A

leaving group leaves, carbocation forms

88
Q

Electronegativity

A

measure of the tendency of an atom to attract a bonding pair of electrons

89
Q

Lowest electronegativity

A

Fr

90
Q

sp2

A

trigonal planar
bent
120°

91
Q

are arrows drawn towards or away from an electrophile?

A

towards

92
Q

step 1 of an Sn1 reaction

A

dissociation of the leaving group forming a carbocation

93
Q

specific rotation

A

observed rotation divided by length and concentration

94
Q

-Ph is

A

benzene

95
Q

levorotary

A

rotates plane polarized light counterclockwise

96
Q

sp

A

linear

180°

97
Q

does the BP/MP of an alkane increase or decrease with branching?

A

increase

98
Q

what happens when you combine an alcohol with HCl?

A

formation of an alkyl halide

99
Q

what are the reactants and products of the pinacol rearrangement?

A

vic-diol to an aldehyde or ketone

acid catalyzed

100
Q

Exceptions to the octet rule

A

H/He stable with two valence electrons

B/Be stable with six valence electrons

Third period or higher stable with expanded octets

101
Q

sp3

A

tetrahedral
trigonal pyramidal
bent
109.5°

102
Q

Highest electronegativity

A

F

103
Q

octet rule

A

atoms gain or lose electrons to obtain exactly 8 electrons in their valence shell

104
Q

dextrorotary

A

rotates plane polarized light clockwise

105
Q

How many steps are in an E2 reaction?

A

one

106
Q

stereoisomers

A

same formula, same bond-to-bond connectivity, different in the 3D arrangement of the substituents

107
Q

anti addition

A

two new bonds are formed on opposite sides

108
Q

How many steps are in an Sn2 reaction?

A

one

109
Q

axial

A

rise vertically

110
Q

Structural isomers

A

same formula, different bond-to-bond connectivity

111
Q

hemiketal

A

ketal with one -OR group replaced with -OH

112
Q

what molecules does an Sn2 reaction favor?

A

good nucleophiles, 1/2° carbons

113
Q

what are the steps of the pinacol rearrangement?

A

vic-diol plus acid protonates -OH to -OH2+ and water leaves forming a carbocation, methyl shifts are possible
resonance with the OH and carbocation to oxygen double bond and removal of H to a ketone or aldeyhde

114
Q

name three reducing agents

A

NaBH4
LiAlH4
H2 and pressure

115
Q

horizontal lines on a fischer projection

A

out of the page

116
Q

Alkene

A

at least one c-c double bond

117
Q

What happens when a 3° alcohol is combined with an oxidizing agent?

A

no reaction

118
Q

Electronegativity of F

A

4

119
Q

how do you synthesize an alkane from an alkene

A

H2 and a metal catalyst (Pd)

120
Q

Which is stronger, a sigma or pi bond? why?

A

sigma bond because they have more overlap

121
Q

actual structure

A

weighted average of all resonance contributors

more stable structures contribute more

122
Q

Electronegativity of H

A

2.2

123
Q

name three common oxidizing agents

A 
O3
Cr2O7
CrO4
KMnO4
PCC
PDC
Collins
Jones
124
Q

are alcohols more or less acidic than water?

A

less

125
Q

What happens when a 2° alcohol is combined with an oxidizing agent?

A

ketone

126
Q

absolute configurations

A

R and S
assign priority to all substituents based on molecular weight, rotate lowest priority to the back
clockwise 1-3: R
counterclockwise 1-3: S

127
Q

step 2 of an Sn1 reaction

A

attack of carbocation by the nucleophile

128
Q

what can be used to reduce an acid or ester

A

LiAlH4

129
Q

bonds broken and reformed via radical reaction

A

combustion

130
Q

chiral center

A

atom attached to four different substituents

131
Q

How does an alkyl halide form from an alcohol?

A

Sn2 or Sn1
add acid with halide to protonate alcohol, loss of -H2O and attack of carbocation or molecule by the halide to form alkyl halide

132
Q

Allyl

A

methylene bridge attached to a vinyl group

133
Q

-C6H5 is

A

benzene

134
Q

what groups are electron donating?

A

negative

135
Q

Alkyne

A

at least one c-c triple bond

136
Q

TMS

A

trimethylsiyl ether

137
Q

by what mechanism is a 2/3° alcohol dehydrated?

A

E1

138
Q

What molecule reacts with an alcohol to form R-Cl

A

SOCl2

139
Q

(+)

A

dextrorotary

140
Q

Sigma Bond

A

Formed by head-on overlapping between atomic orbitals

141
Q

Alkane

A

all c-c and c-h single bonds

142
Q

vicinal

A

bonded to adjacent atoms

143
Q

What happens when a 1° alcohol is combined with an oxidizing agent?

A

aldehyde, carboxylic acid

144
Q

sulphone

A

SO2 attached to two carbons

145
Q

Single bond is a

A

sigma bond

146
Q

Amide

A

nitrogen single bonded to C of carbonyl

147
Q

aromaticity

A

cyclic or planar molecule with a ring of resonance bonds that exhibits more stability than other geometric arrangements with the same set of atoms

148
Q

Coordinate covalent bonds

A

both electrons shares in the bond are donated by one atom

149
Q

anomers

A

differ only in their spatial orientation at the anomeric carbon of a ring

150
Q

equatorial

A

extend horizontally

151
Q

what does the opening of an epoxide form?

A

alcohol

152
Q

what molecules does an E2 reaction favor?

A

strong or bulky bases

153
Q

acyl

A

alkyl group with a carbon double bonded to oxygen

154
Q

aryl

A

aromatic ring with one H removed

155
Q

step 2 of an E1 reaction

A

base abstracts H from carbocation molecule and alkene forms

156
Q

what are the steps in a grignard synthesis?

A

grignard attacks a carbonyl, acid donates a proton to O- forming an alcohol

157
Q

does the BP/MP of an alkane increase or decrease with molecular weight?

A

increase

158
Q

Geminal

A

bonded to the same atom

159
Q

the second and third bonds between two elements are

A

pi bonds

160
Q

step 1 of an Sn2 reaction

A

back side attack of the electrophile with simultaneous ejection of the leaving group

161
Q

What characteristics make up an E2 reaction

A

elimination, bimolecular

reaction rate depends of the concentration of two species

162
Q

ketone

A

carbonyl group bonded to two hydrocarbon groups

163
Q

What groups are electron withdrawing?

A

positive

164
Q

are bases a function of thermodynamics or kinetics?

A

thermodynamics

165
Q

Enantiomers

A

stereoisomers that are non-identical, non-superimposable mirror images of one another

166
Q

are alkenes electro or nucleophilic?

A

nucleophilic

167
Q

tosyl

A

methyl group para substituted on benzene to SO3-R

168
Q

Electronegativity of Fr

A

0.7

169
Q

How is a tosylate/methylate formed?

A

tox/mes-Cl reacts with an alcohol, Cl- leaves and removes H from the molecule to form HCl and tos/mes-OR

170
Q

carbonyl

A

carbon double bonded to oxygen

171
Q

VESPR stands for

A

valence shell electron pair repulsion theory

172
Q

valence

A

number of bonds an atom “normally” makes

173
Q

Less stable bonds have ____ heats of combustion

A

higher

174
Q

Carboxylic Acid

A

organic acid containing COOH

175
Q

a double bond has

A

one sigma and one pi bond

176
Q

Which atom is partially positive in a nitro group

A

nitrogen

177
Q

(-)

A

levorotary

178
Q

example of coordinate covalent

A

iron in hemoglobin

179
Q

What molecule reacts with an alcohol to form R-Br

A

PBr3

180
Q

Alkyl

A

hydrocarbon radical from removal of a hydrogen

181
Q

dipole moment (u)=

A

charge*distance

distance between charges

182
Q

What characteristics make up an Sn1 reaction

A

substitution, unimolecular

reaction rate depends on the concentration of the reactant only

183
Q

Diastereomers

A

two molecules with the same formula and bond-to-bond connectivity that are non-identical but are not mirror images

MCAT 1 (10 decks)

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