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Organic Chemistry Flashcards

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1
Q

If an alcohol is the second highest priority in a compound, what name root will that compound include?

A

hydroxy-

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2
Q

If a compound contains an alcohol as its highest priority substituent, what would the name of it end in?

A

-ol (ex. ethanol)

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3
Q

If a compound has two alcohols on the same carbon, and those alcohols are the highest substituent, what would the name of the compound include? What type of alcohol would it be?

A

-diol

and it would be a geminal diol

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4
Q

If a compound has two alcohols on adjacent carbons, and those alcohols are the highest substituent, what would the name of the compound include? What type of alcohol would it be?

A

-diol

and it would be a vicinal diol (same VICINITY as each other)

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5
Q

If a compound contains an aldehyde as its highest priority substituent, what would its name end in?

A

-al (ex. ethanal)

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6
Q

If a compound contains a ketone as its highest priority substituent, what would its name end in?

A

-one (ex. acetone)

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7
Q

What is the name for the carbon that is two away from the carbonyl carbon?

A

The beta carbon

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8
Q

If a compound contains an aldehyde or ketone but they aren’t the highest priority substituent, what would the name include to indicate these functional groups?

A

oxo-

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9
Q

If a compound contains a carboxylic acid, what will the name end with?

A

-oic acids (ex. ethanoic acid)

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10
Q

What is the longest carbon chain in formic, acetic, and propionic acid?

A

Formic- 1 carbon

Acetic- 2 carbons

Propionic- 3 carbons

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11
Q

If a compound contains an ester as its highest priority substituent, what will the name end with?

A

-oate (ex. ethyl propanoate)

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12
Q

How are amides named?

A

By adding “amide” to the end of the name

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13
Q

How are anhydrides named?

A

By adding “anhydride” to the end of the name

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14
Q

What is the order of priority of functional groups?

A
  1. Carboxylic Acid (Highest Oxidation State)
  2. Anhydride
  3. Ester
  4. Amide
  5. Aldehyde
  6. Ketone
  7. Alcohol
  8. Alkene/Alkyne
  9. Alkane (Lowest Oxidation State)
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15
Q

If two compounds have the same molecular formula but different connectivity what type of isomers are they?

A

Structural (Constitutional) Isomers

ex. hexane vs. 2 methyl pentane

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16
Q

What physical and chemical properties do constitutional isomers share?

A

None

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17
Q

If two compounds have the same molecular formula and the same connectivity what broad group of isomers do they fall under?

A

Stereoisomers

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18
Q

If two compounds are the exact same but only differ in their rotation around sigma bonds, what type of isomers are they?

A

Conformational Isomers

ex. a chair flip

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19
Q

In a Newman projection when the two highest priority substituents line up in the same plane, what conformation is this called?

A

Totally Eclipsed

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20
Q

What are the interactions that occur between groups in a Newman projections that have large sizes?

A

Gauche Interactions

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21
Q

For a conformational isomer in a Newman projection, which conformation is the most energetically favorable?

A

Staggered Anti

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22
Q

For a conformational isomer in a Newman projection, which conformation is the least energetically favorable?

A

Eclipsed Syn

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23
Q

What is the difference between angle strain and torsional strain within a ring molecule?

A

Angle Strain- bond angles are forced to deviate from their ideal angle

Torsional Strain- occurs when cyclic molecules are forced into eclipsed or gauche conformations

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24
Q

What is the most stable conformation of cyclohexane?

A

Chair Conformation

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25
Q

What is the least stable conformation of cyclohexane?

A

Boat Conformation

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26
Q

In a chair flip what happens to the atoms that were axial and pointing out of the page?

A

These atoms will become equatorial but will still point out of the page

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27
Q

Is it more stable for a large substituent on a ring to be in the axial or equatorial position?

A

equatorial

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28
Q

Two compounds have the same molecular formula, same connectivity, but differ in their arrangement in space and cannot be interconverted by breaking some of their bonds. What type of isomers are these compounds?

A

Configurational Isomers

ex. R vs. S

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29
Q

How would someone be able to differentiate between two enantiomers?

A

They rotate plane polarized light to equal but opposite angles

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30
Q

What is the level to which a molecule (usually an enantiomer) rotates plane polarized light called?

A

Optical Activity

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31
Q

What is the equation for the specific rotation of light that an enantiomer causes?

A

angle = observed rotation/ c x l
Where:
c = concentration
l = path length in dm

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32
Q

If a solution has equal parts of an R and S enantiomer it is said to be what?

A

A Racemic Mixture

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33
Q

If two compounds differ at one chiral center but the same at another, what type of configurational isomers are they?

A

Diasteriomers

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34
Q

If a compound has two chiral centers that are the opposite absolute configuration but also has a plane of symmetry, what type of compound is it?

A

A Meso compound

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35
Q

What molecules take the highest priority when trying to determine absolute configuration?

A

The substituents with the highest atomic number

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36
Q

In a Fischer projection are the substituents to the side coming out of or going into the page?

A

They are coming out of the page

thus if H is on the side the absolute configuration that is found must be reversed

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37
Q

What do the quantum numbers tell us about specific electrons?

A

Their most likely location within an atom

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38
Q

How many pi and sigma bonds are in a double bond?

A

Sigma- 1

Pi- 1

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39
Q

How many pi and sigma bonds are in a triple bond?

A

Sigma- 1

Pi- 2

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40
Q

What is stronger, a singular sigma bond or a singular pi bond?

A

A singular sigma bond

which is why pi bonds are often broken in reactions

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41
Q

How much S character does a SP3 orbital have?

A

25%

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42
Q

Which is a stronger acid, Alkane or Alkene?

A

Alkene

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43
Q

Which is a stronger acid, H2 or Alkene?

A

H2

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44
Q

Which is a stronger acid, Alkyne or Amine?

A

Alkyne

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45
Q

Which is a stronger acid, Ketone or an Ester?

A

Ketone

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46
Q

Which is a stronger acid, Alcohol or a Water molecule?

A

Water

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47
Q

Which is a stronger acid, Alcohol or a Ester?

A

Alcohol

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48
Q

As a molecule becomes more and more positive, what happens to the acidity?

A

Acidity increases with charge

ex. NH3 < NH4+

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49
Q

As the atom to which hydrogens are bound to increases in atomic radius, what happens to the acidity?

A

Acidity increases with increases atomic radius of bound atom

ex. HF < HI

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50
Q

If one atom has a more stable conjugate base than another due to resonance stabilization, which atom has a higher acidity?

A

Acidity increases as the stabilization of the conjugate base increases

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51
Q

Why does a molecule of CH2IOH have a lower acidity than CH2FOH?

A

Because F has a higher inductive effect on the conjugate base than does I

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52
Q

As acid strength increases, what happens to nucleophilicity?

A

It decreases

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53
Q

What makes a good leaving group?

A

The weaker basicity that a leaving group has the better it is

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54
Q

What type of reactant has a high affinity for electrons?

A

An Oxidizing agent

because it wants to take H+ from other molecules

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55
Q

Why are transition metals found in many reducing and oxidizing agents?

A

Because they have multiple oxidation states that allows them to hold many H+ and then give them to the compound they are reacting with

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56
Q

What oxidizing agents are thought of as weak?

A
  1. PCC
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57
Q

What oxidizing agents are thought of as strong?

A
  1. CrO3/Pryindine
  2. H2CrO4
  3. KMnO4
  4. O3
  5. H2O2 (mCPBA)
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58
Q

What are some reducing agents?

A
  1. LiAlH4

2. NaBH4

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59
Q

Can alcohols hydrogen bond?

A

Yes

60
Q

When an alcohol is attached to a aromatic ring what is this compound called?

A

Phenol

61
Q

If a compound had multiple alcohol groups added to it, what would happen to the boiling point?

A

It would increase greatly

62
Q

If you treat a primary alcohol with a weak oxidizing agent (PCC) what will form?

A

An Aldehyde

63
Q

If you treat a secondary alcohol with a weak oxidizing agent (PCC) what will form?

A

A Ketone

64
Q

If you treat a primary alcohol with a strong oxidizing agent (Na2Cr2O7) what will form?

A

A Carboxylic acid

65
Q

Is the Jones Oxidation a weak or strong oxidizer?

A

Strong (CrO3)

66
Q

How can an alcohol be made into a better leaving group?

A

Through the addition of a mesylate (-SO3CH3) or a tosylate (Aromatic Ring + mesylate)

67
Q

If two equivalents of an alcohol (or a diol) are reacted to make a protecting group on an aldehyde, what is formed?

A

An Acetal (2 OR groups on a primary carbon)

68
Q

If two equivalents of an alcohol (or a diol) are reacted to make a protecting group on a ketone, what is formed?

A

A Ketal (2 OR groups on a secondary carbon)

69
Q

How are ketals and acetals removed from protecting a compound?

A

By adding an aqueous acid

70
Q

When you oxidize a phenol what do you get?

A

A Quinone

71
Q

What is the general structure of a Quinone?

A

A phenol ring with two carbonyl groups attached

72
Q

What is the general structure of a Hydroxyquinone?

A

A Quinone with one or more extra alcohol groups

73
Q

What is the best solvent for an SN2 reaction to occur?

A

Polar Aprotic

74
Q

What is the best solvent for an SN1 reaction to occur?

A

Polar Protic

75
Q

If an aldehyde is attached to a ring what name is added to the compound?

A

-carbaldehyde

76
Q

In a carbonyl compound, is the carbon electrophilic or nucleophillic?

A

electrophilic

77
Q

If you treat an primary alcohol with PCC, what will form?

A

An Aldehyde

78
Q

What happens in a nucleophilic attack on a carbonyl?

A

A nucleophile attacks the carbon of the carbonyl and then the Pi electrons are pushed up onto the oxygen

79
Q

How are geminal diols formed?

A

A water molecule (usually catalyzed by acid) attacks a carbonyl

80
Q

What occurs when one equivalent of an alcohol is left to react with a carbonyl containing compound?

A

A hemiacetal or hemiketal is formed

81
Q

What occurs when two equivalents of an alcohol is left to react with a carbonyl containing compound?

A

A acetal or ketal is formed

82
Q

What occurs when a nitrogen containing compound reacts with a carbonyl containing compound?

A

A Imine is formed

83
Q

What is a cyanohydrin?

A

A compound that contains a alcohol and a cyanide attached to the same carbon

84
Q

When a HCN acts as a nucleophile for a carbonyl containing compound, what forms?

A

A Cyanohydrin

85
Q

What are the alpha hydrogens on an aldehyde or a ketone containing compound?

A

The hydrogens that are bonded to the carbon that is adjacent to the carbonyl group

86
Q

Why are alpha hydrogens more acidic than normal?

A

The conjugate base is stabilized via resonance contribution from the carbonyl group

87
Q

How is an enolate formed?

A

The removal of the proton on a enol (a compound with a double bond adjacent to an alcohol group)

88
Q

Describe what happens in the Michael addition

A

A enolate acts as a electrophile and attacks an alpha/beta carbonyl compound

89
Q

What is the difference between a kinetic and thermodynamic enolate?

A

Kinetic- formed faster but less stable

Thermodynamic- formed slower but more stable

90
Q

Describe what happens in an Aldol condensation

A

An aldehyde or ketone acts as both a electrophile (in its keto form) and as a nucleophile (in its enolate form) to attack itself and form a new carbon-carbon bond

91
Q

What is the difference between nucleophilic substitution in carboxylic acids compared to ketones/aldehydes?

A

Carboxylic acids (and their derivatives) have a leaving group

92
Q

What is a cyclic amide called?

A

A Lactam

93
Q

Describe the process of fischer esterification of a carboxylic acid

A

The carboxylic acid is protonated (making the carbon more electrophilic) then an alcohol attacks the carbon which then eventually kicks off one of the -OH groups leaving an ester

94
Q

What are cyclic esters called?

A

Lactones

95
Q

When two carboxylic acids condense together what is formed?

A

An Anhydride

96
Q

What is a Beta-Keto acid?

A

A compound that contains two carboxylic acids that are one carbon away from each other

97
Q

Describe the process of decarboxylation

A

A Beta-Keto Acid forms intramolecular bonds causing the removal of a CO2 and you are left with a ketone

98
Q

Describe the structure of soaps

A

Soaps have deprotonated carboxylic acids with long fatty chains that organize themselves into micelles (acid heads facing outward and hydrocarbon tails facing inward)

99
Q

What are two common cyclic anhydride compounds?

A

Phthalic anhydride
and
Succinic anhydride

100
Q

What is the order of carboxylic acid derivatives in terms of reactivity toward nucleophilic attack?

A
  1. Acyl Chlorides
  2. Anhydrides
  3. Carboxylic Acids = Esters
  4. Amides
101
Q

If a nucleophile (such as NH3) attacks and anhydride what reaction occurs and what are the products?

A

This reaction is called an anhydride cleavage
Products:
1) A carbonyl group attached to the attacking nucleophile
2) A carboxylic acid

102
Q

When an alcohol attacks an ester and acts as a nucleophile what reaction occurs and what are the products?

A

This reaction is called a transesterification
Products:
1) A new ester with the new -OR group
2) A primary alcohol

103
Q

What isomer of amino acids occurs naturally in the body?

A

L-isomer

104
Q

What are two ways of synthesizing amino acids?

A

Strecker Synthesis
and
Gabriel Synthesis

105
Q

Describe what happen in the Strecker Synthesis

A

1) An aldehyde is protonated with a ammonium and then the nitrogen does a nucleophilic attack to form an Imine
2) A nitrile attacks the imine forming an aminonitrile [nitrogen and nitrile present]
3) The aminonitrile is protonated and water then attacks twice as a nucleophile
4) Another ammonia attacks as a nucleophile this creating a compound with a carboxylic acid, nitrogen and and R group that comes from the original aldehyde (An Amino Acid)

106
Q

Describe what happens in the Gabriel Synthesis

A

1) Start with Potassium Phthalimide and Diethyl Bromomalonate that combine in an SN2 reaction
2) A base is added to make the SN2 addition of an R-Br group more favorable
3) The dicarboxylic acid is decarboxylated to cleave the primary amine

107
Q

What does spectroscopy measure?

A

Measures the energy differences between the possible states of a molecular system by determining the frequencies of different electromagnetic radiation emissions

108
Q

Which type of spectroscopy measures the molecular vibrations (bond streching, bond bending) by passing infrared light through a substance and measuring the absorbance of different peaks?

A

Infrared Spectroscopy

109
Q

A scientist can look at the region on an IR spectroscopy graph and tell exactly what the compound is. What region of the chart is this called?

A

Fingerprint Region (400-1500 cm-1)

110
Q

In an IR spectroscopy what is the difference between an alcohol, amine, and a carboxylic acid peak?

A

The carboxylic acid peak is broad like a beard while the alcohol is a sharper peak and the amine is the sharpest peak

111
Q

Where do -OH bonds show up on an IR spectroscopy?

A

3100-3500 cm-1

112
Q

Where do -NH bonds show up on an IR spectroscopy?

A

3100-3500 cm-1

113
Q

Where do carbonyl bonds show up on an IR spectroscopy?

A

1650-1800 cm-1

114
Q

Where do -CH bonds from alkanes show up on an IR spectroscopy?

A

2800-3000 cm-1

115
Q

Where do -CH bonds from alkenes show up on an IR spectroscopy?

A

3100-3200 cm-1

116
Q

Where do -CH bonds from alkynes show up on and IR spectroscopy?

A

3300 cm-1

117
Q

What type of spectroscopy uses ultraviolet light that is passed through a sample that has been dissolved in an inert substance?

A

UV spectroscopy

118
Q

What is UV spectroscopy best at measuring?

A

The presence of conjugated systems in a compound

119
Q

How is nuclear magnetic resonance (NMR) spectroscopy done?

A

A compound is exposed to a magnetic field and its atomic nuclei will orient in certain ways in response to the magnetic field. Then radiofrequency pulses are sent through the sample allowing for the absorption of certain frequencies by the sample, which is recorded

120
Q

Why is TMS used in NMR spectroscopy?

A

TMS is the baseline reference peak that gives a signal at 0 ppm

121
Q

How does H-NMR tell us about the different types of hydrogen molecules in a sample?

A

The number of peaks represents the number of different hydrogens

122
Q

How does H-NMR tell us about the total number of hydrogens in a sample?

A

The total number of hydrogens would be the sum of all the integration numbers from the different peaks

123
Q

If a peak representing hydrogens in H-NMR is shifted further to the left, what does this mean about those hydrogens?

A

These hydrogens are in a more electronegative bond (aldehyde, close to a halogen)

124
Q

How does H-NMR tell us about the numbers of neighboring hydrogen that a specific hydrogen will have?

A

The number of peaks minus 1 (n - 1) in a specific band will tell us how many neighboring hydrogens there are

125
Q

Where do hydrogens on carboxylic acids appear on H-NMR?

A

10-12 ppm

126
Q

Where do hydrogens on aldehydes appear on H-NMR?

A

9-10 ppm

127
Q

Where do hydrogens on aromatic compounds appear on H-NMR?

A

6-8.5 ppm

128
Q

If a compound is found to have only Van Der Waals interactions, what phase in an extraction setup would you most likely find it?

A

The organic phase

129
Q

If a compound is found to have hydrogen bonding, what phase in an extraction setup would you most likely find it?

A

The aqueous phase

130
Q

If a the organic phase is less dense than the aqueous phase would it be on the top or bottom of the separation funnel?

A

The top

131
Q

What is the difference between a regular extraction and a wash?

A

In an extraction the compound of interest is removed (usually in the aqueous phase)

In a wash the compound of interest is left in the separation funnel

132
Q

Describe the process of recyrstallization

A

The product is dissolved in a hot solvent and then as the solvent cools the purified product will crystalize out of the solution due to a decreased solubility

133
Q

How does a vacuum setup effect a distillation?

A

It is used to distill compounds with a boiling point over 150 Celsius. This is because the vacuum lowers the vapor pressure and thus lowers the boiling point and allows the desired product to distill at a lower (safer) temperature

134
Q

What is the difference between a regular distillation and a fractional distillation?

A

A fractional distillation separates two liquids with very similar boiling points (less than 25 Celsius apart). It does this by increasing the surface area of the condensing tube to allow for maximal time for the higher boiling point liquid to condense back into the flask

135
Q

What is the difference between the stationary phase and the mobile phase in chromatography?

A

Stationary Phase- the medium through which the mobile phase will run through. Its properties (polar, charged, etc.,) will determine what is being measured

Mobile Phase- the substances that are being tested and compared

136
Q

How are thin-layer and paper chromatography similar?

A

They both use a polar stationary phase

  • Thin layer uses silica or alumina
  • Paper uses cellulose
137
Q

Will a non-polar substance travel farther or shorter up the stationary phase in thin-layer and paper chromatography?

A

It will travel far up because it is not attracted to the polar stationary phase

138
Q

How is reverse phase chromatography different from thin-layer chromatography?

A

Reverse phase uses a non-polar stationary phase

139
Q

How is retardation factor found (Rf)

A

Rf = distance spot moved / distance solvent front moved

140
Q

What is the difference between thin-layer chromatography and column chromatography?

A

In column chromatography, the mobile phase is pulled down through a column (filled with the stationary phase) by gravity

141
Q

What type of chromatography uses charged substances as the stationary phase in a column setup?

A

Ion-exchange chromatography

142
Q

What type of chromatography uses beads with tiny pores to separate out large vs small compounds (done with a column setup)?

A

Size-exclusion chromatography

143
Q

In size-exclusion chromatography, would a larger or smaller compound elute first?

A

A larger compound

144
Q

What type of chromatography uses a column setup to separate out different proteins?

A

Affinity Chromatography

145
Q

How is gas chromatography unique?

A

The mobile phase is a vaporized gas that travels through a long coil and elutes onto a detector that is read by a computer setup

146
Q

What type of chromatography uses a liquid that is highly pressurized through the stationary phase and the elutent rate is measured by a computer?

A

High Performance Liquid Chromatography

147
Q

What does a high Rf value indicate?

A

the substance being measured traveled farther in down the stationary phase

MCAT (8 decks)

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