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Organic Chemistry Flashcards

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MCAT flashcards
1
Q

conjugation

A

3 or more adjacent pi orbitals

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2
Q

aromatic compounds

A

have a planar structure developed

n+2 is the number of pi electrons. n can be any integer

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3
Q

How can you determine what is a stronger acid?

A

look at the stability of the conjugate base

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4
Q

How can you determine a stronger base?

A

look at the stability of the conjugate base, see what is a better acid and do the opposite

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5
Q

What is a stronger acid: carboxylic acid or phenol?

A

carboxylic acid since you can make resonance structures with the negative oxygen

carboxylic acid has a very stable conjugate base, making it a strong acid

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6
Q

Thermodynamic characteristics of alkanes

A

low melting/boiling points since they only have london dispersion forces between them

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7
Q

volatile

A

refers to molecules with low boiling points

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8
Q

Two ways to form alkyl halides

A

heating diatomic molecules to form free radicals, then the free radical will react with the hydrocarbon

or, hydrohalogenation

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9
Q

hydrohalogenation

A

addition of a halogen atom to the double bond of an alkane

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10
Q

Why are alkyl halides so reactive?

A

they possess a great leaving group (halide) and they pull electrons from carbon making carbon electrophilic

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11
Q

phenyl

A

benzene ring

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12
Q

How can you reduce an alkene to an alkane?

A

through hydrogenation, add more hydrogen

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13
Q

isomers

A

molecules that share the same formula but differ in structure

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14
Q

structural isomers

A

also called constitutional isomers

connectivity is different

have to break bonds to convert between structural isomers

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15
Q

tautomers

A

structural isomers that interconvert with one another and exist together in equilibrium

connectivity differs, this is not resonance!

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16
Q

example of tautomers

A

keto-enol tautomer

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17
Q

conformational isomers

A

how single bonds are arranged in space

rotation around a single bond can convert between conformational isomers

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18
Q

where should bulky constituents be placed in the most stable chair conformation?

A

they should be placed equatorially

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19
Q

geometric isomers

A

a type of configurational isomer

configuration around a double bond

cis/trans or E/Z

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20
Q

E configuration

A

highest priority groups are on opposite sides of the double bond

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21
Q

Is Z the same as cis?

A

no

Z refers to highest priority groups, while cis refers to the same groups. Nitpicky detail

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22
Q

Z configuration

A

highest priority groups are on same side of the double bond

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23
Q

enantiomers

A

a pair of non-superimposable mirror images

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24
Q

How can two molecules with multiple chiral centers be enantiomers?

A

if the molecules have different configurations at the same location

ex: RRS / SSR

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25
Q

racemic mixture

A

mixture of 50/50 enatiomers cannot rotate light

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26
Q

What are some ways to separate enatiomers?

A

use chiral chromatography

interactions with a chiral ligand

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27
Q

What is the D/L orientation of most amino acids?

A

L

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28
Q

What is the D/L orientation of most saccharides?

A

D

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29
Q

What is the relationship between D/L?

A

they are enantiomers

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30
Q

diastereomers

A

have different configurations at some but not all locations

ex: RRR / SSR

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31
Q

epimers

A

stereoisomers that differ at just one chiral center

ex: RRS / RRR

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32
Q

meso compounds

A

have an internal plane of symmetry which makes them achiral

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33
Q

Can meso compounds be enantiomers?

A

no, since they are achiral

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34
Q

Where do you start numbering a Fischer projection of a carbohydrate?

A

at the top carbon

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35
Q

Where do you start numbering a Haworth projection of a carbohydrate?

A

at the anomeric carbon

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36
Q

Where does the anomeric carbon come from?

A

it is the original carbonyl carbon in the aldose/ketose that was attacked by an -OH group

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37
Q

Where does the oxygen that attacked the carbonyl group to cyclize end up on Haworth projection?

A

the oxygen ends up in the ring

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38
Q

What do aldoses lead to?

A

hemiacetal anomeric carbons

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39
Q

What do ketoses lead to?

A

hemiketal anomeric carbons

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40
Q

Is the anomeric carbon directly attached to two oxygens?

A

yes

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41
Q

furanose

A

a cyclic carbohydrate with a 5 membered ring

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42
Q

pyranose

A

a cyclic carbohydrate with a 6 membered ring

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43
Q

can furanoses have 6 carbons?

A

yes, that would be a hexose furanose

furanose just tells us about the ring NOT about the number of carbons

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44
Q

where does the right side of Fischer projection point in Haworth projection?

A

down

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45
Q

alpha anomer

A

anomeric hydroxyl group points down

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46
Q

beta anomer

A

anomeric hydroxyl group points up

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47
Q

mutarotation

A

moves between beta and alpha anomers

need to break a bond for mutarotation to occur

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48
Q

What determines melting points and boiling points?

A

intermolecular interactions

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49
Q

More -OH groups results in what?

A

higher melting point

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50
Q

Water’s pKa

A

14

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51
Q

How can you make alcohols more acidic?

A

add electron withdrawing group

then, when the -OH proton is removed the conjugate base can better distribute the negative charge

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52
Q

How can you make alcohols less reactive?

A

add electron donating group

EDG will make the conjugate base less stable, and therefore the alcohol is less likely to react

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53
Q

-al

A

aldehyde

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54
Q

-one

A

ketone

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55
Q

-oic acid

A

caboxylic acid

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56
Q

What can primary alcohols become?

A

primary alcohols can become either aldehydes or be further oxidized to carboxylic acids

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57
Q

What can secondary alcohols become?

A

secondary alcohols can be oxidized to ketones

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58
Q

What can tertiary alcohols become?

A

3º alcohols cannot be further oxidized

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59
Q

PCC

A

a weak oxidizing agent

can turn hydroxyls into carbonyl

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60
Q

Example of stronger oxidizing agents

A

molecules with Cr and Oxygen

or molecules with a metal and oxygen

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61
Q

Alcohols in synthesis reactions

A

if we want to protect the alcohol, need to use a protecting group

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62
Q

protecting groups

A

silyl ethers, mesylates, and tosylates

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63
Q

How can mesylates and tosylates be used?

A

they can act as either protecting groups or make a species into a better leaving group

64
Q

How can you use alcohols to protect groups like aldehydes?

A

use alcohols to convert the carbonyl into a non-reducable acetal group

65
Q

nomenclature for positions on phenol

A

ortho is next to the -OH group

meta is in the middle

para is directly across from the -OH group

66
Q

quinone

A

an oxidized version of a diphenol

not aromatic

67
Q

ubiquinone

A

coenzyme Q

an important electron receptor in the ETC

can carry up to two electrons

68
Q

acetone structure

A

a ketone with two methyl groups

69
Q

What is a good solvent for SN2 reactions?

A

aldehydes and ketones since they are polar aprotic solvents

70
Q

What has a higher melting point, alcohols or ketones?

A

alcohols cause they can participate in more H-bonding

71
Q

Where is the alpha carbon?

A

the alpha carbon is adjacent to the carbonyl carbon

72
Q

What is more acidic, aldehyde or ketone?

A

aldehyde

aldehydes have a more stable conjugate base because a ketone’s methyl group acts as a EDG, which makes conjugate base less stable

73
Q

How can you deprotonate alpha carbon of ketone?

A

need a very strong base

74
Q

Beta-dicarbonyls

A

more acidic at their middle alpha carbon due to resonance

75
Q

can you oxidize ketones?

A

no

76
Q

How can you oxidize aldehydes?

A

need a strong oxidizing agent

PCC will NOT be strong enough

77
Q

What are common nucleophilic attackers of carbonyl groups?

A

water

alcohols

cyanide

78
Q

What forms when alcohol reacts with ketones?

A

form a hemiketal

alcohols tend to keep reacting and form a ketal

79
Q

What forms when alcohol reacts with aldehydes?

A

form a hemiacetal

alcohols tend to keep reacting and form a acetal

80
Q

What forms when aldehyde is reacted with amine?

A

imine

81
Q

acetic acid structure

A

carboxylic acid with methyl

82
Q

formic acid structure

A

carboxylic acid with hydrogen

simplest carboxylic acid

83
Q

inductive effect

A

highly electronegative species pull ED down the molecule

can stabilize conjugate base

84
Q

what is more important inductive effect or resonance?

A

resonance

85
Q

saponification

A

mix triglyceride with strong base

break ester bonds in triglyceride

form carboxylate anion that forms a salt with a nearby metal cation

86
Q

DIBAL

A

weak reducing agent

87
Q

decarboxylation

A

carboxyl group is lost at CO2

favored at high temps

88
Q

biochemical example of decarboxylation

A

pyruvate to acetyl-CoA

89
Q

Hell-Volhard-Zelinsky Halogenation overall

A

carboxylic acid is converted to an alpha-halo acid

still have a carboxylic acid, just with a halogen on the alpha carbon

90
Q

Hell-Volhard-Zelinsky Halogenation steps

A

acyl halide is made from carboxylic acid

tautomerization occurs and forms carbon double bond

halogen attacks the double bond

results in halogen attached to alpha carbon of an acyl halide

add water to convert the acyl halide to a carboxylic acid

91
Q

What are cyclic amides called?

A

lactams

92
Q

What are cycle esters called?

A

lactones

93
Q

Boiling points of amides

A

lower than carboxylic acids and alcohols

94
Q

transesterfication

A

switches ester with a new alcohol

95
Q

acid-catalyzed amide hydrolysis

A

hydrolyze amide to form carboxylic acid and amine

this is what happens in peptide bond hydrolysis

96
Q

List the reactivity of carboxylic acid derivatives from least to most reactive

A 
Carbonate anion 
Amide
Carboxylic acid
Ester
Anhydride
Acyl halide
97
Q

Acyl halide

A

halogen attached to a carbonyl group

98
Q

What does the reaction rate depend upon in SN1 reactions?

A

just the concentration of the substrate

99
Q

What does the reaction rate depend upon in SN2 reactions?

A

the concentration of the substrate and nucleophile

100
Q

How many steps is an SN1 reaction?

A

2 steps

First, the carbocation is formed and then the nucleophile attacks

101
Q

How many steps is an SN2 reaction?

A

1 step

simultaneous nucleophilic attack and leaving group departure

102
Q

What is the rate limiting step of an SN1 reaction?

A

the formation of the carbocation

103
Q

Stereochemistry of SN1 reactions

A

since the nucleophile can attack the carbocation at either empty p-orbital, a 50-50 racemic mix of enantiomers is produced

104
Q

Stereochemistry of SN2 reactions

A

Due to the backside attack, the sterochem is inverted

105
Q

Would a 3º substrate be likely to react through SN1 or Sn2 mechanism?

A

SN1

the 3ºcan stabilize the carbocation and the 3º creates too large of sterics for the SN2 reaction

106
Q

What solvent should we use for SN1 reaction?

A

polar protic solvent

ethanol, water, methanol

107
Q

What solvent should we use for SN2 reaction?

A

polar aprotic solvent

acetone, DMSO, and DMF

108
Q

Fisher esterification

A

turn carboxylic acid into ester with a reaction with an alcohol

reversible through hydrolysis

109
Q

Imine formation

A

react ketone and amine in acidic conditions to form imine

110
Q

E1

A

two steps and is driven by carbocation formation

111
Q

E2

A

only has one step and need a very strong base to occur

112
Q

Nucleophilic addition

A

nucleophile adds itself to electrophile without kicking another group off

113
Q

What is normally the result of nucleophilic addition?

A

a hemiacetal or hemiketal

114
Q

What is needed for nucleophilic addition to take place?

A

a substrate with a double bond or triple bond

115
Q

How does base catalysis work?

A

deprotonate the nucleophile to make it even more nucleophilic

116
Q

What is another example of tautomerism besides keto-enol?

A

imine to enamine

117
Q

Enol

A

C-C double bond with hydroxyl group attached

118
Q

How does keto-enol tautomerism generally work?

A

deprotonate the alpha-carbon to form a C-C double bond

119
Q

Under what conditions will an enolate form?

A

basic conditions

120
Q

Is a keto or enol normally favored?

A

normally the keto form is favored unless enol is stabilized by resonance or H-bonding

121
Q

Enolate

A

anionic intermediates

places a negative charge on the alpha-carbon

122
Q

Kinetic form of enol

A

C-C double bond is on less substituted side

123
Q

Thermodynamic form of enol

A

C-C double bond is on more substituted side

124
Q

When do we see kinetic form of enol?

A

at low temperatures with bulky bases

at low temperatures there is not enough energy to make the more stable product

125
Q

Products of aldol condensation

A

aldol

or dehydration forms alpha, beta - unsaturated ketone

126
Q

Aldol

A

aldehyde and alchohol ketone

127
Q

alpha, beta - unsaturated ketone

A

see after aldol condensation/dehydration

C-C double bond next to a carbonyl group

128
Q

LDA

A

strong, sterically hindered base

commonly used to make kinetic product

129
Q

Michael addition

A

uses enolate as nucleophile and alpha, beta-unsaturated ketone to make 1,5-dicarbonyl

130
Q

Robinson annulation

A

take 1,5-dicarbonyl from Michael addition and do another round of enolate condensation

make an enolate on the 1,5-dicarbonyl and have it attack itself

end up with six membered ring with alpha,beta-unsaturated ketone

131
Q

How can we classify fructose?

A

fructose is a ketohexose that forms a furanose ring

132
Q

What is a common triose?

A

glyceraldehyde

133
Q

What kind of reaction forms a glycosidic bond?

A

dehydration

134
Q

How are glycosidic bonds broken?

A

acid-catalyzed reactions

135
Q

Sucrose

A

glucose and fructose

Glu(a1-B2)Fru

136
Q

Maltose

A

2 glucose molecules

Glu(a1-4)Glu

137
Q

Lactose

A

glucose and galactose

Glu(B1-4)Gla

138
Q

Anomers

A

epimers that differ in orientation of their substituents at the anomeric carbon

139
Q

Where is the anomeric carbon in the Fischer projection?

A

the anomeric carbon is the carbon in carbonyl group

140
Q

Difference between hemiketal and ketal group?

A

hemiktal group has 1 -OH and 1 -OR

ketal group has 2 -ORs

141
Q

What does nucleophilic attack on a trigonal planar substrate produce?

A

a mix of isomers

142
Q

Millard reaction

A

reacts amino acids with reducing sugars

143
Q

reducing sugars

A

act as reducing agents and become oxidized

144
Q

Are monosaccharides reducing sugars?

A

yes, all monosaccharides are reducing sugars

145
Q

How do ketoses act as reducing sugars?

A

keto-enol tautomerisation allows them to act as aldoses

146
Q

Tollen’s test

A

uses Ag+ as an oxidizing agent to test for the presence of reducing sugars

Ag+ will be reduced to Ag(s) and produce silver coat

147
Q

Benedict’s test

A

uses Cu2+ as an oxidizing agent to test for the presence of reducing sugars

Cu2+ is reduced to Cu+ which causes a color change from blue to red

148
Q

How to remember Benedict versus Tollen’s test?

A

Benedict = BLUE

149
Q

What is the relationship between glucose and galactose?

A

they are diasteromers at carbon 4

150
Q

What is the relationship between D-glucose and L-glucose?

A

they are enantiomers because they differ at each stereocenter

151
Q

Lowercase d/l (+/-) naming system

A

d is if the light is rotated to the right

l is if the light is rotated to the left

152
Q

D/L naming system

A

look at last -OH group on Fischer projection

if it points left, L

if it points right, D

153
Q

What type of amines can participate in H-bonding?

A

primary and secondary

154
Q

Aryls

A

like phenyls but with NH2 instead of -OH

155
Q

Are thiols capable of hydrogen bonding?

A

capable of very weak H-bonding

156
Q

Thiols versus alcohols acidity

A

Thiols are more acidic because sulfurs are larger and can spread out the negative charge more that oxygens

157
Q

-oate

A

indicates an ester

MCAT Prep (22 decks)

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