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MCAT > MCAT Ochem > Flashcards

MCAT Ochem Flashcards

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1
Q

What are the prefixes for the first 12 alkanes?

A 
Meth 
Eth 
Prop
But
Pent
Hex
Hept
OCt
Non
Dec
Undec
Dodec
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2
Q

What are the 5 steps used to name alkanes according to IUPAC rules?

A
  1. Find the longest chain
  2. Number the chain so that the lowest set of numbers is obtained for the substituents
  3. Name and alphabetize the substituents
  4. Assign a number to each substituent
  5. Complete the name
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3
Q

In the case of an “en - ol” which carbon receives the lowest number?

A

The carbon attached to the alcohol group is assigned the lowest number

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4
Q

What is a diol?

A

A diol is a molecule with 2 hydroxyl (OH) groups

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5
Q

T/F: An aldehyde has a carbonyl group somewhere in the middle of a carbon chain.

A

False, In an aldehyde, the carbonyl group is at the end of the carbon chain

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6
Q

T/F: A ketone has a carbonyl group at one end of a carbon chain.

A

False, In a ketone, the carbonyl group is somewhere in the middle of the carbon chain

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7
Q

In the case of an “en - one” which carbon receives the lowest number?

A

The carbonyl carbon receives the lowest number

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8
Q

What type of compound does a -COOH group denote?

A

The COOH group denotes a carboxylic acid

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9
Q

What are the common names for the following:

1) methanoic acid
2) ethanoic acid
3) propanoic acid

A
  1. formic acid
  2. acetic acid
  3. propionic acid
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10
Q

Name the prefix and suffix for the following:

  1. Carboxylic Acid
  2. Ester
  3. Acyl Halide
A
  1. carboxy- / -oic acid
  2. alkoxycarbonyl- / -oate
  3. halocarbonyl- / -oyl halide
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11
Q

Name the prefix and suffix for the following:

  1. Amide
  2. Nitrile
  3. Aldehyde
A
  1. amido - / -amide
  2. cyano - / -nitrile
  3. oxo- / -al
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12
Q

Name the prefix and suffix for the following:

  1. Ketone
  2. Alcohol
  3. Thiol
A
  1. oxo - / -one
  2. hydroxy - / -ol
  3. sulfhydryl- / -thiol
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13
Q

Name the prefix and suffix for the following:

  1. Amine
  2. Ether
  3. Sulfide
A
  1. amino- / -amine
  2. alkoxy- / -ether
  3. alkylthio- / -sulfide
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14
Q

Name the prefix and suffix for the following:

  1. Nitro
  2. Azide
  3. Diazo
A
  1. nitro- / ~
  2. azido - / -azide
  3. diazo- / ~
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15
Q

What is structural isomer?

A

Structural isomers have the same chemical formulas, but different atomic connectivity

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16
Q

What is a stereoisomer?

A

Stereoisomers are compounds that differ only in respect to the spatial arrangement of their atoms

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17
Q

Order the following conformations of n-butane according to energy levels (low to high): gauche, anti, eclipsed, totally eclipsed

A

Anti, gauche, eclipsed, totally eclipsed

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18
Q

Order the above hexanes according to energy levels (low to high)

A

Low to high: chair, twisted boat, boat

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19
Q

T/F: Axial hydrogens are parallel to the ring

A

False, axial hydrogens are perpendicular to the ring

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20
Q

T/F: Bulky groups prefer the equatorial position over the axial position

A

True

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21
Q

What are geometric isomers?

A

Geometric isomers are molecules that differ with respect to the spatial relationship of substituents around a doable bond

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22
Q

What is a chiral molecule?

A

A chiral molecule is a molecule that is not superimposable upon its mirror image.

Chiral Can’t superimpose

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23
Q

What are enantiomers?

A

Enantiomers are chiral molecules that are non-superimposable mirror images of each other.

CHIRAL
MIRROR IMAGES
CAN’T SUPERIMPOSE

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24
Q

T/F: Achiral molecules are optically active

A

False, achiral molecules are optically inactive

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25
Q

What is a dextrorotatory (+) compound?

A

A dextrorotatory compound rotates polarized light to the right (clockwise)

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26
Q

What is a levorotatory (-) compound?

A

A levorotatory compound rotates polarized light to the left (counterclockwise)

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27
Q

what is a racemic mixture?

A

A racemic mixture contains equal amounts of both enantiomers

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28
Q

How many stereoisomers are possible for a molecule with four chiral centers?

A

2^4 = 16

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29
Q

What are diastereomers?

A

Diastereomers are stereoisomers that are not mirror images of each other

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30
Q

What types of molecules are optically active?

A

Chiral molecules are optically active

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31
Q

What is a meso compound?

A

A meso compound is a molecule that possesses stereocenters but has a plane of symmetry. It is achiral and therefore optically inactive.

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32
Q

What type of chemical bond involves the sharing of electrons?

A

Covalent bonds involve the sharing of electrons

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33
Q

What type of chemical bond involves the transfer of electrons?

A

Ionic bonds involve the transfer of electrons

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34
Q

Which orbital has a spherical shape?

A

”s” orbitals are spherically shaped

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35
Q

Which orbital has a bi-lobed shape?

A

“p” orbitals are bi-lobed

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36
Q

T/F: All single bonds are sigma (σ) bonds

A

True

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37
Q

What type of bond results when two p orbitals overlap?

A

Two overlapping p orbitals form a pi (π) bond

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38
Q

What are the components of a double bond?

A

A double bond is composed of 1 sigma and 1 pi bond

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39
Q

What are the components of a triple bond?

A

A triple bond is composed of 1 sigma and 2 pi bonds

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40
Q

T/F: A pi bond can exist without a sigma bond

A

False, a pi bond cannot exist independently of a sigma bond

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41
Q

Which type of bond (π or σ) is stronger?

A

A sigma bond is generally stronger than a pi bond

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42
Q

What is the hybridization of the carbon atom in CH4? what are the bond angles?

A

sp^3, 109.5 degrees

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43
Q

What is the bond angle between sp hybridized atoms?

A

180 degrees

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44
Q

What is the bond angle between sp^2 hybridized atoms?

A

120 degrees

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45
Q

How many other carbons are 1°, 2°, 3°, and 4° carbons bonded to?

A

1, 2, 3, and 4 other carbons respectively

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46
Q

How does increasing molecular weight affect the boiling point and melting point of an alkane?

A

Increased molecular weight results in INCREASED boiling and melting points

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47
Q

How does increased branching affect the boiling point of an alkane?

A

Increased branching LOWERS the boiling point

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48
Q

What are the 3 steps of a halogenation reaction?

A

The three steps are:
initiation
propagation
termination

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49
Q

What is the order of free radical stability?

A

3°>2°>1°> methyl

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50
Q

What type of reaction involves breaking down large alkanes into smaller ones?

A

Pyrolysis or “cracking” uses heat to break down large alkanes into smaller ones

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51
Q

What are the products of the complete combustion of an alkane?

A

the complete combustion of an alkane produces:
CO2
H2O
heat

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52
Q

Is a nucleophile electron rich or electron poor?

A

A nucleophile is electron rich

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53
Q

All else being equal, how does basicity affect the strength of a nucleophile?

A

The stronger the base, the stronger the nucleophile

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54
Q

How many steps are involved in an SN1 reaction? What are they?

A

There are 2 steps in an SN1 reaction. 1st - the molecule dissociates into a carbocation and a leaving group.

2nd - the nucleophile combines with the carbocation

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55
Q

What is the order of carbocation stability?

A

3°>2°>1°>methyl

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56
Q

Which step in an SN1 reaction is the rate determining step

A

The first step, the formation of the carbocation is the rate determining step

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57
Q

T/F: The rate of an SN2 reaction is dependent on the concentration of the nucleophile

A

False, the rate is only dependent on the concentration of the original molecule

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58
Q

How can SN1 reaction rate be increased?

A
  1. Stabilize the carbocation by increasing substitution and using a highly polar solvent
  2. Use a better leaving group (weak base)
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59
Q

How does basicity affect the nature of a leaving group?

A

The weaker the base, the better the leaving group

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60
Q

How many steps are involved in an SN2 reaction?

A

SN2 reactions have one step. concerted

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61
Q

Is the rate of an SN2 reaction dependent on the concentration of the substrate, of the nucleophile or both?

A

The SN2 reaction rate is dependent on the concentration of both the substrate and the nucleophile

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62
Q

T/F: SN1 reactions involving a chiral substrate produce an optically active mixture

A

False, a racemic mixture results during SN1 reactions with an optically active reactant

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63
Q

T/F: SN2 reactions involving a chiral substrate result in an inverted, optically active product

A

True

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64
Q

Which type of reaction is favored (SN1 or SN2) given the following conditions?

Polar protic solvent

A

SN1

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65
Q

Which type of reaction is favored (SN1 or SN2) given the following conditions?

Polar aprotic solvent

A

SN2

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66
Q

Which type of reaction is favored (SN1 or SN2) given the following conditions?

Methyl or 1 alkyl halide

A

Methyl or 1 alkyl halides favor SN2

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67
Q

Which type of reaction is favored (SN1 or SN2) given the following conditions?

3 alkyl halide

A

3 alkyl halides favor SN1

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68
Q

T/F: E1 and SN1 reactions are driven by the same factors (polar solvent, good leaving groups, highly branched chains, etc)

A

True

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69
Q

Which form of an alkene has a higher melting point (cis or trans)?

A

the trans form of an alkene has a higher melting point due to its symmetry

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70
Q

Which form of an alkene has a higher boiling point (cis or trans)?

A

The cis form of an alkene has a higher boiling point due to its polarity

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71
Q

T/F: The reduction of an alkyne on a metal surface (Pd) results in a cis alkene

A

False, It results in an alkane

72
Q

T/F: The reduction of an alkyne in Na and NH3 produces a trans alkene

A

True

Pd metal: alkyne —–> alkane
Na and NH3: alkyne —–> trans alkene

73
Q

Does the electrophilic addition of HBr to an alkyne follow Markovnikov’s rule?

A

Yes, electrophilic addition of HBr to an alkyne or an alkene follows Markovnikov’s rule

74
Q

Does the free radical addition of HBr to an alkyne follow Markovnikov’s rule?

A

No, free radical addition of HBr to an alkyne or an alkene does not follow Markovnikov’s rule (ROOR peroxides)

75
Q

What is an aromatic compound?

A

An aromatic compound is defined as any unusually stable ring system. Aromatic compounds are cyclic, conjugated polyenes that follow Huckel’s rule

76
Q

What is an aliphatic compound?

A

An aliphatic compound is any non-aromatic compound

77
Q

What is Huckel’s rule?

A

Huckel’s rule states that an aromatic compound has (4n+2) π electrons, where n is any nonnegative integer

78
Q

What is an antiaromatic compound?

A

An antiaromatic compound is a cyclic conjugated polyene with 4n electrons

79
Q

Do electron donating groups activate or deactivate an aromatic ring?

A

Electron donating groups activate the ring

80
Q

How do electron withdrawing groups affect the reactivity of an aromatic ring?

A

Electron withdrawing groups deactivate a ring

81
Q

List the activating groups:

A 
NR2
CH3
OCOR
NH2
OR

all ortho/para directing

82
Q

List the Deactivating groups:

A

COOH
NO2
COOR
SO3H

all meta directors

83
Q

What is the exception for Deactivating groups?

A

F, Cl, Br, I are all deactivating but are ORTHO/PARA DIRECTING!

84
Q

T/F: Activating compounds are always o/p directors

A

True

85
Q

T/F: Deactivating compounds are always meta directors

A

False, halogens (Cl, I, Br, F) are deactivating and o-p directing

86
Q

Why do alcohols have a significantly higher boiling point than analogous alkanes?

A

Alcohols can hydrogen bond

87
Q

T/F: Phenols are less acidic than aliphatic alcohols

A

False, phenols are much more acidic than aliphatic alcohols.

88
Q

What are the 3 types of reactions used to synthesize alcohols?

A

Addition
Substitution
Reduction

89
Q

Can a tertiary alcohol be easily oxidized?

A

No, tertiary alcohols cannot be oxidized without cleavage of a carbon-carbon bond

90
Q

Can ethers hydrogen bond?

A

No, ethers do not hydrogen bond

91
Q

How does the boiling point of an aldehyde (or ketone) compare with its analogous alkane? Alcohol?

A

The boiling point of an aldehyde is HIGHER than that of the corresponding alkane but LOWER than that of the corresponding alcohol

92
Q

How is a ketone or an aldehyde produced from an alcohol?

A

Oxidizing an alcohol will produce the corresponding ketone or aldehyde (i.e. by using PCC, or Na2Cr2O7)

93
Q

How do you produce a ketone or aldehyde from an alkene?

A

Ozonolysis of an alkene will produce corresponding ketones or aldehydes as cleavage products

94
Q

Which protons relative to a carbonyl group are acidic?

A

Alpha protons relative to a carbonyl group are slightly acidic.

95
Q

What happens when aldehydes or ketons react with water?

A

Aldehyde and ketons react with water to form gem-diols

96
Q

T/F: a reaction in which 2 molecules combine with the loss of a water molecule is a condensation reaction

A

True

97
Q

What would be the product when acetaldehyde is reacted with dilute NaOH?

What is the name of this type of reaction?

A

an aldol (be able to draw)

Adol condensation

98
Q

What are the common names for the first three straight chain carboxylic acids?

A

The first 3 carboxylic acids are:
formic acid
acetic acid
propionic acid

99
Q

T/F: Alcohols have higher boiling points than carboxylic acids

A

False, carboxylic acids have higher boiling points than corresponding alcohols

100
Q

How do electron withdrawing groups (-Cl, -NO2) attached to the alpha carbon affect the acidity of a carboxylic acid?

A

Electron withdrawing groups increase acidity

101
Q

How do electron donating groups (-NH2, -OCH3) attached to the alpha carbon affect the acidity of a carboxylic acid

A

Electron donating groups decrease acidity

102
Q

Would you have to oxidize or reduce an aldehyde to create a carboxylic acid?

A

Oxidation of an aldehyde creates a carboxylic acid

103
Q

Which type of alcohol (1°,2°, or 3°) can be oxidized to a carboxylic acid?

A

1° alcohols can be oxidized to carboxylic acids; however, 2° and 3° alcohols cannot

104
Q

What is a micelle? IS the interior hydrophobic or hydrophilic?

A

When placed in an aqueous solution, soap molecules arrange themselves into spherical structures call micelles.

The soap molecules arrange themselves such that their POLAR heads face outward and their NONPOLAR chains face inward.

105
Q

Would you have to oxidize or reduce a carboxylic acid to prepare an alcohol?

A

Reduction of a carboxylic acid forms an alcohol

106
Q

T/F: Acid chlorides are very reactive

A

True

107
Q

How do electron donating grousp affect the acidity of benzoic acid?

A

Electron donating groups reduce the acidity of benzoic acid

108
Q

How do electron withdrawing groups affect the acidity of benzoic acid?

A

Electron withdrawing groups increase the acidity of benzoic acid.

109
Q

T/F: Anhydrides react under the same conditions as acid chlorides

A

True

110
Q

What is the product of the hydrolysis of an amide under acidic conditions

A

The hydrolysis of an amide under acidic conditions will produce a carboxylic acid

111
Q

What are the products of the hydrolysis of an ester?

A

The products are a carboxylic acid and an alcohol

112
Q

What is saponification?

A

Saponification is the process whereby fats are hydrolyzed, under basic conditions, to produce soaps

113
Q

T/F: A glycerol molecule attached to two carboxylic acids and one phosphoric acid is a phospholipid

A

True

114
Q

How many alkyl groups are in a tertiary amine

A

A 3° amine has 3 alkyl groups attached to the nitrogen

115
Q

What is a quaternary ammonium compound?

A

A quaternary ammonium compound is a nitrogen atom attached to 4 alkyl groups. The nitrogen is positively charged and, therefore, the compounds exists as a salt.

116
Q

T/F: An imine is a compound with a carbon-nitrogen double bond

A

True

117
Q

Which type of amines can form hydrogen bonds?

A

1° and 2° amines can form hydrogen bonds

118
Q

What separation technique makes use of two immiscible solvents?

A

Extraction makes use of two immiscible solvents

119
Q

What separation technique can be used to isolate a solid from a liquid?

A

Filtration can be used to isolate a solid from a liquid

120
Q

T/F: Recrystallization is a process in which impure crystals are dissolved in hot solvent and then recrystallize as pure crystals as the solvent cools.

A

True

121
Q

Which purification technique involves a solid turning directly into a gas?

A

Sublimation occurs when a solid turns directly into a gas

122
Q

Which separation technique can be used to separate a mixture of particles with difference densities and masses?

A

Centrifugation separates based on mass and density

123
Q

Which separation technique takes advantage of a solution containing two or more compounds with different boiling points?

A

Distillation separates based on different boiling points

124
Q

T/F: Vacuum distillation can be used to separate liquids with very high boiling points

A

True

125
Q

Which separation technique separates compounds based upon their different affinities for a medium?

A

Chromatography separates compounds based on their different affinities for a medium

126
Q

What is the Rf value in thin layer chromatography(TLC)?

A

The Rf value is the distance a compound travels divided by the distance the solvent travels

127
Q

Would a compound with a high Rf value be near the top or near the bottom of a TLC plate?

A

A compound with a high Rf value would be near the top of a TLC plate

128
Q

Which separation technique uses an electric field?

A

Electrophoresis uses an electric field

129
Q

T/F: Isoelectric focusing uses a gel with a pH gradient to separate proteins based on their isoelectric points

A

True

130
Q

SDS-polyacrylamide gel electrophoresis separates proteins based on what factor?

A

SDS-polyacrylamide gel electrophoresis separates proteins based on their masses

131
Q

T/F: Agarose gel electrophoresis is used to separate fragments of nucleic acid

A

True

132
Q

What type of spectroscopy is useful for identifying functional groups?

A

IR spectroscopy is useful for identifying function groups. NMR has limited utility in this area

133
Q

Do symmetrical stretches exhibit an IR absorption signal?

A

No, Symmetrical stretches do no exhibit an IR absorption signal

134
Q

T/F: NMR spectroscopy can be used to identify distinct 1H protons in a molecule

A

True

135
Q

How many different NMR peaks (doublets, triplets, etc) would appear if the molecule being analyzed were:

Ethane

A

1 singlet

136
Q

How many different NMR peaks (doublets, triplets, etc) would appear if the molecule being analyzed were:

Propane

A

1 septet (7) and 1 triplet

137
Q

How many different NMR peaks (doublets, triplets, etc) would appear if the molecule being analyzed were:

1,3- dichloropropane

A

1 quintet (5) and 1 triplet

138
Q

How many different types of equivalent protons are there in 1-bromo-2-chloropropane

A

There are 3 different types of equivalent protons in 1-bromo-2-chloropropane

139
Q

T/F: NMR can make use of both 12C and 13C

A

False, 12C has no magnetic moment and therefore, cannot be used in NMR spec

140
Q

What type of spectroscopy is ideal for the study of conjugated olefins?

A

UV-vis spectroscopy is ideal for the study of conjugated olefins

141
Q

What type of spectroscopy can determine the molecular weight of a compound?

A

Mass spectroscopy determines the molecular weight of a compound

142
Q

T/F: Monosaccharides undergo many of the same reactions as alcohols

A

True

143
Q

What is the general formula for calculating the maximum number of possible stereoisomers of a molecule?

A

The general formula is 2^n where n=number of chiral centers

144
Q

A pyranose has how many members in its ring?

A

A pyranose has a six-member ring

145
Q

A furanose has how many members in its ring?

A

A furanose has a five-member ring

146
Q

T/F: When converting a Fischer Projection to a Haworth (ring) Projection, groups on the right side of a Fischer Projection will be pointing upward

A

False, groups on the right side of a Fischer Projection end up pointing downward in a Haworth Projection

147
Q

What monosaccharides maek up a molecule of maltose?

A

Maltose is composed of two molecules of glucose

148
Q

Does cellulose contain β-1,4 glycosidic bonds or α-1,4 glycosidic bonds?

A

Cellulose contains β-1,4 glycosidic bonds

149
Q

Do starch and glycogen contain β-1,4 glycosidic bonds or α-1,4 glycosidic bonds?

A

Starch and glycogen contain α-1,4 glycosidic bonds

150
Q

What is mutarotation?

A

Mutarotation is the spontaneous change of configuration about the C1 that occurs when monosaccharides are exposed to water

151
Q

T/F: Glucose is an aldohexose

A

True

152
Q

T/F: Fructose is an aldopentose.

A

False, fructose is ketohexose

153
Q

What is a reducing sugar?

A

A reducing sugar is any monosaccharide with a hemiacetal ring

154
Q

T/F: The alpha carbon is chiral in all amino acids

A

False, glycine’s alpha carbon has 2 hydrogens and is therefore not chiral

155
Q

What is a zwitterion?

A

A zwitterion is a species with both a positive and negative charge

156
Q

Define amphoteric

A

An amphoteric species can act as either a base or an acid

157
Q

In what direction will an amino acid with a neutral side chain move during electrophoresis at pH 4:

If the pI of the amino acid is 7?

A

The amino acid will have a net POSITIVE charge and therefore will move towards the CATHODE

158
Q

In what direction will an amino acid with a neutral side chain move during electrophoresis at pH 4:

if the pI of the amino acid is 3?

A

The amino acid will have a net NEGATIVE charge and therefore move towards the ANODE

159
Q

In what direction will an amino acid with a neutral side chain move during electrophoresis at pH 4:

If the pI of the amino acid is 4?

A

The amino acid is at its isoelectric point and will not move

160
Q

T/F: The buffering capacity of an amino acid is greatest at its isoelectric point

A

False, the buffering capacity of an amino acid is least at its isoelectric point. It is greatest at its two or more pKa’s

161
Q

Where are non-polar amino acids usually found in a protein and why?

A

non-polar amino acids are usually found in the interior of a protein because they are hydrophobic

162
Q

Where are polar amino acids usually found in a protein?

A

Polar amino acids are usually found on the exterior of a protein

163
Q

What is the net charge of an acidic amino acid at physiological pH

A

The net charge of an acidic amino acid at physiological pH is negative

164
Q

What is the net charge of a basic amino acid at physiological pH?

A

The net charge of a basic amino acid at physiological pH is POSITIVE

165
Q

What type of bond joins amino acids?

A

a peptide bond joins amino acids together

166
Q

Define the primary structure of a protein

A

Primary structure refers to the sequence of amino acids

167
Q

Define the secondary structure of a protein

A

Secondary structure refers to hydrogen bond interactions within the protein

168
Q

What are the two most common types of secondary structure?

A

The two most common types of secondary structure are α-helix and β-pleated sheet

169
Q

Define tertiary structure

A

Tertiary structure refers to the three-dimensional folding of a protein.

170
Q

What are the two primary classifications (regarding tertiary structure) of proteins?

A

Fibrous and globular proteins

171
Q

Define quaternary structure

A

Quaternary structure only exists in proteins with more than one polypeptide subunit. It refers to the way the subunits arrange themselves

172
Q

What is a conjugated protein

A

A conjugate protein is a protein that derives part of its function from a prosthetic group

173
Q

What happens when a protein denatures? What can cause a protein to denature?

A

A protein loses its three-dimensional shape when it denatures. Changes in temperature, pH, and solute concentration can cause denaturation.

174
Q

What is the difference between an ester and an ether?

A

ESTER = think carbonyl bonded to another O

Ether: batman wing. 1 O in middle of 2 R groups

175
Q

Careful: aromatic vs anti-aromatic vs aliphatic

A

aromatic = planar, conjugated, follows 4n+2 Huckel’s rule.

anti-aromatic = 4n

aliphatic = any non-aromatic compound!

MCAT (4 decks)

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