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ORGANIC CHEM Flashcards

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1
Q

If all prefixes were dropped, what would be the name of the parent root of this molecule?

A

Propanoic acid

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2
Q

What are the common names for ethanal, methanal, and ethanol?

A

Acetaldehyde, formaldehyde, ethyl alcohol

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3
Q

Which of the following are considered terminal functional groups:

aldehydes, ketones, carboxylic acids

A

Aldehydes and carboxylic acids

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4
Q

What is they highest-priority functional group in this molecule?

A

Anhydride

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5
Q

The IUPAC name for the following structure ends in what suffix?

A

-oic acid

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6
Q

What is the proper structure for 2,3-dihydroxybutanedioic acid (tartaric acid)?

A

B

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7
Q

The common names for the aldehydes and carboxylic acids that contain only one carbon start with which prefix?

A

Form-

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8
Q

What is the IUPAC name for the following structure?

A

2,5 - dimethylheptane

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9
Q

What is the IUPAC name for the following structure

A

3-ethyl-2,5,5-trimethylhexane

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10
Q

The IUPAC name for the following structure starts with what prefix?

A

2-methyl-

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11
Q

NADH is a coenzyme that releases high-energy electrons into the electron transport chain. It is known as nicotinamide adenine dinucleotide or diphosphopyridine nucleotide. What functional groups exist in this molecule?
I. Phosphate
II. Amide
III. Anhydride

A

I and II only

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12
Q

Pyruvic acid, one of the end products of glycolysis, is commonly called acetylformic acid. Based on its common name, the structure of pyruvic acid must be:

A

A

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13
Q

Which of the following are common names for carboxylic acid derivatives?
I. Acetic anhydride
II. Formic acid
III. Methyl formate

A

I and III only

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14
Q

Consider the names 2,3-diethylpentane. Based on the structure implies by this name, the correct IUPAC name for this molecule is:

A

3-ethyl-4-methylhexane

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15
Q

Oxidation state increases with more bonds to _______ and decreases with more bonds to ___________

A

heteroatoms (atoms besides carbon and hydrogen. Like Oxygen, nitrogen, phosphorus, and halogens)

hydrogen

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16
Q

What is a carbonyl group

A

It is a carbon double-bonded to an oxygen

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17
Q

What carbonyl carbon will always have the ketone on carbon 2 by default?

A

Propanone

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18
Q

What are the 5 steps of IUPAC nomenclature and name a molecule:

A
  1. Identify the longest carbon chain containing the highest-order functional group
  2. number the chain
  3. name the substituents
  4. Assign a number to each substituent
  5. complete the name
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19
Q

Alkanes are hydrocarbons without any double or triple bonds. They have a general formula:

A

C

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20
Q

Alkanes are named according to the number of carbons present followed by the suffix:

A: ion
B: ane
C: ene
D: yne

A

B

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21
Q

Alkenes are named by numbering the double bond by its lower-numbered carbon. And replacing the suffix with:

A: ion
B: ane
C: ene
D: yne

A

C

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22
Q

Alkynes are named by numbering the double bond by its lower-numbered carbon. And replacing the suffix with:

A: ion
B: ane
C: ene
D: yne

A

D

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23
Q

Alcohols are named by substituting the suffix with ______ or by using the prefix hydroxy- if a higher-priority group is present

A: ol
B: ane
C: ene
D: yne

A

A

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24
Q

Diols contain two hydroxyl groups. They are termed geminal if on ________ carbon or vicinal if on _______ carbons.

A

Same
Adjacent

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25
Q

Simplified version of terminal and non-terminal carbon. Which one is on the extremes (ends) and which one is any carbon in any area but the ends?

A

Terminal carbon: Ends
Non-terminal carbon: Middles

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26
Q

Aldehydes contain a carbonyl group (a carbon double-bonded to an oxygen) and are located on the terminal carbon. They are named with the suffix ____, or by using the prefix ____ if a higher-priority group is present

A

-al
oxo-

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27
Q

Ketones contain a carbonyl group (a carbon double-bonded to an oxygen) and are located on the non-terminal carbon. They are named with the suffix ____, or by using the prefix ____ if a higher-priority group is present

A

-one
oxo- or keto-

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28
Q

There are 4 carbonyl-containing compounds. What are they

A
  • Aldehydes
  • Ketones
  • Carboxylic acids
  • Derivatives
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29
Q

Carboxylic acids contain _____ bonds to oxygen. And are always ______

A: two; terminal
B: three; terminal
C: three; nonterminal
D: two; nonterminal

A

B

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30
Q

Carboxylic acids are named with the suffix:

A

-oic acid

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31
Q

Ester are carboxylic acid derivatives where -OH is replaced with -OR and used the suffix ____ or the prefix _______

A

-oate
alkocarbonyl-

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32
Q

Amides replace the hydroxyl group of carboxylic acid with amino group and use the suffix ____ or the prefix ____

A

-amide
carbamoyl- or amido-

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33
Q

Anhydrides are formed from two carboxylic acids by dehydration and can be symmetric, asymmetric, or cyclic and are named using the suffix ______

A

anhydride

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34
Q

How are functional groups arranged in order of priority?

A: Alkane, anhydride, ester, amide, aldehyde, ketone, carboxylic acid, alcohol, alkene or alkyne, alkane
B: Carboxylic acid, anhydride, ester, amide, aldehyde, ketone, alkane, alkene or alkyne, alcohol
C: Carboxylic acid, anhydride, aldehyde, amide, ketone, ester, alcohol, alkene or alkyne, alkane
D: Carboxylic acid, anhydride, ester, amide, aldehyde, ketone, alcohol, alkene or alkyne, alkane

A

D

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35
Q

Which of the following does NOT show the optical activity?

A: (R)-2-butanol
B: (S)-2-butanol
C: A solution containing 1 M (R)-2- butanol and 2 M (S)-2-butanol
D: A solution containing 2 M (R)-2- butanol and 2 M (S)-2-butanol

A

D

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36
Q

How many stereoisomers exist for the following aldehyde?

A

8

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37
Q

Which of the following compounds is optically inactive?

A

C

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38
Q

Cholesterol, shown below, contains how many chiral centers?

A

8

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39
Q

Which isomer of the following compound is the most stable?

A

B

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40
Q

The following reaction results in

A: Retention of relative configuration and a change in the absolute configuration
B: a change in the relative and absolute configurations
C: retention of the relative and absolute configurations
D: retention of the absolute configuration and a change in the relative configuration

A

C

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41
Q

The following molecules are considered to be:

A: enantiomers
B: diastereomers
C: meso compounds
D: structural isomers

A

A

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42
Q

(+)-Glyceraldehyde and (-)-glyceraldehyde refer to the (R) and (S) forms of 2,3-dihydroxypropanal, respectively. These molecules are considered:

A: enantiomers
B: diastereomers
C: meso compounds
D: structural isomers

A

A

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43
Q

Consider (E)-2-butene and (Z)-2-butene. This is a pair of what types(s) of isomers?

i. cis-trans isomers
ii. diastereomers
iii. enantiomers

A: i only
B: ii only
C: i and ii only
D: i and iii only

A

C

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44
Q

3-methylpentane and hexane are related in that they are:

A: enantiomers
B: diastereomers
C: constitutional isomers
D: conformational isomers

A

C

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45
Q

(R)-2-chloro-(S)-3-bromobutane and (S)-2-choloro-(S)-3-bromobutane are:

A: enantiomers
B: diastereomers
C: meso compounds
D: the same molecule

A

B

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46
Q

Omeprazole is a proton pump inhibitor commonly used in gastroesophageal reflux disease. When omeprazole, a racemic structure, went off-patent, pharmaceutical companies began to manufacture esomeprazole, the (S)-enantiomer of omeprazole, by itself. Given 1 M solutions of omeprazole and esomeprazole, which solution(s) would likely exhibit optical activity?

A: omeprazole
B: esomeprazole only
C: both omeprazole and esomeprazole
D: neither omeprazole nor esomeprazole

A

B

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46
Q

A scientist takes 0.5 g/ml solution of an unknown pure dextrorotatory organic molecule and places it in a tube with a diameter of 1cm. He observes that a plane of polarized light is rotated 12 degrees under these conditions. What is the specific rotation of this molecule?

A: -240 degrees
B: -24 degrees
C: +24 degrees
D: +240 degrees

A

D

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46
Q

(2R,3S)-2,3-dihydroxybutanedioic acid and (2S,3R)-2,3-dihydroxybutanedioic acid are:
i. meso compounds
ii. the same molecule
iii. enantiomers
A: i only
B: iii only
C: i and ii only
D: i and iii only

A

C

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47
Q

Staggered conformations have groups ____ degrees apart, as seen in a Newman projection.

A

60

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47
Q

if the methyl groups of butane are 120 degrees apart, as seen in a newman projection, this molecule is in its:

A: highest-energy gauche form
B: lowest-energy staggered form
C: middle-energy eclipsed form
D: highest-energy eclipsed form

A

C

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47
Q

in anti staggered molecules, the two largest groups are _____ degrees apart, and strain is minimized

A

180

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48
Q

in gauche staggered molecules, the two largest groups are _____ degrees apart

A

60

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49
Q

Eclipsed conformations have groups directly in ___________ of each other as seen in a Newman projection

A

front

50
Q

in totally eclipsed conformations, the two largest groups are direction in _______ of each other and stain is maximized

A

front

51
Q

The stain in cyclic molecules comes from angle strain, torsional strain, and nonbonded strain and usually adopt _______ shapes to minimize this strain

A

nonplanar shapes

52
Q

Substituents attached to a cyclohexane can be classified as _________ or ____________ equatorial

A

axial
equatorial

53
Q

enantiomers are _________________ images and thus have opposite stereochemistry at every chiral carbon

A: nonsuperimposable mirror
B: superimposable mirror

A

A

54
Q

Optical activity refers to the ability of a molecule to rotate plane-polarized light: d- or _____ molecules rotate light to the right; 1- or _______ molecules rotate light to the left

A: (+)
B: (-)
C: (R)
D: (S)

A

A

55
Q

Meso compounds with an internal plane of symmetry will be ______________ because of the two sides of the molecule cancel each other out

A: inoptically inactive
B: optically inactive
C: optically active
D: inoptically active

A

B

56
Q

diastereomers are ____________ stereoisomers. They have different chemical and physical properties:

A: non-mirror-image
B: mirror image

A

A

57
Q

cis-trans isomers are a subtype of diastereomers in which groups differ in position about an ____________
A: inactive bond
B: moveable bond
C: immovable bond
D: active bond

A

C

58
Q

chiral centers have ____ different groups attached to the central carbon
A: 6
B: 2
C: 3
D: 4

A

D

59
Q

Absolute configuration gives stereochemistry of a compound without having to compare to other molecules and uses Cahn-Ingold-Prelog priority rules

A: in which priority is given by looking at the atoms NOT connected to the chiral carbon or double-bonded carbons; whichever has the highest atomic number gets highest priority
B: in which priority is given by looking at the atoms connected to the chiral carbon or double- bonded carbons; whichever has the lowest atomic number gets highest priority
C: in which priority is given by looking at the atoms connected to the chiral carbon or double-bonded carbons; whichever has the highest atomic number gets highest priority
D: in which priority is given by looking at the atoms connected to the chiral carbon or double- bonded carbons; whichever has the highest atomic number gets lowest priority

A

C

60
Q

an alkene is ____ if the highest-priority substituents are on the same side of the double bond and ____ if on opposite sides

A: (R) & (S)
B: (Z) & (E)
C: (E) & (Z)
D: (S) & (R)

A

B

61
Q

a stereocenter’s configuration is determined by putting the lowest priority group in the back and drawing a circle. If this circle is clockwise the stereocenter is ____; if it is counterclockwise the stereocenter is ____

A: (R) & (S)
B: (Z) & (E)
C: (E) & (Z)
D: (S) & (R)

A

A

62
Q

Within one principal energy level, which subshell has the least energy?

A: s
B: p
C: d
D: f

A

A

63
Q

Which of the following compounds possess at least one σ bond?

A: CH4
B: C2H2
C: C2H4
D: All of the following above contain at least one σ bond

A

D

64
Q

A carbon atom participates in one double bond. As such, this carbon contain orbital with:

A: hybridization between the s-orbital and one p-orbital
B: hybridization between the s-orbital and two p-orbitals
C: hybridization between the s-orbital and three p-orbitals
D: unhybridized s character

A

B

65
Q

The hybridizations of the carbon and nitrogen atoms in CN- are:

A: sp^3 and sp^3, respectively
B: sp^3 and sp, respectively
C: sp and sp^3, respectively
D: sp and sp, respectively

A

D

66
Q

Which of the following hybridization does the Be atom in BeH2 assume?

A: sp
B: sp^2
C: sp^3
D: sp^3d

A

A

67
Q

two atomic orbitals may combine to form

i. a bonding molecule orbital
ii. an antibonding molecular orbital
iii. hybridized orbitals

A: I only
B: III only
C: I and II only
D: I,II, and III

A

D

68
Q

molecular orbitals can contain a maximum of

A: one electron
B: two electrons
C: four electrons
D: 2n^2 electrons, where n is the principal quantum number of the combining atomic orbitals

A

B

69
Q

π bonds are formed by which of the following orbitals?

A: two s-orbitals
B: two p-orbitals
C: one s- and one p- orbitals
D: two sp^2-hybridized orbitals

A

B

70
Q
A

A

71
Q

The four C-H bonds of CH4 point toward the vertices of a tetrahedron. This indicates that the hybridization of the carbon atom in methane is:

A: sp
B: sp^2
C: sp^3
D: sp^3d

A

C

72
Q

Why is a single bond stronger than a π bond:
i. π bonds have greater orbital overlap
ii. s-orbitals have more overlap than p-orbitals
iii. sp^3 hybridization is always unstable

A: i only
B: ii only
C: i and iii only
D: ii and iii only

A

B

73
Q

the p character of the bonds formed by the carbon atom in HCN is:

A: 25%
B: 50%
C: 67%
D: 75%

A

B

74
Q

The resonance structure describes:

i. the hybrid of all possible structures that contribute to electron distribution
ii. a potential arrangement of electrons in a molecule
iii. the single form that the molecule most often takes

A: I
B: II
C: I & II
D: I, II, & III

A

B

75
Q

An electron is known to be in the n=4 shell and the i=2 subshell. How many possible combinations of quantum numbers could this electron have?
A: 1
B: 2
C: 5
D: 10

A

D

76
Q

Compared to single bonds, triple bonds are:
A: weaker
B: longer
C: made up of fewer σ bonds
D: more rigid

A

D

77
Q

Quantum numbers describe the ____________________ and number of ___________ an element possesses

A

size, shape, orientation

atomic orbitals

78
Q

the principal quantum number, n, describes the energy level (shell) in which an electron resides and indicates the distance from the nucleus to the electron. Its possible values range from ___________

A

1 to infinite

79
Q

the azimuthal quantum number, 1, determines the subshell in which electron resides. Its possible values range from ___________

A

0 to n-1

80
Q

the magnetic quantum number, mp, determines the orbital in which electron resides. Its possible values range from ____________

A

-1 to +1

81
Q

the spin quantum number, ms, describes the spin of an electron. Its possible values are _______

A

+_ 1/2

82
Q

Which of the following are Lewis bases?
i. Ag+
ii. H2O
iii. NH3

A: I
B: I & II
C: II & III
D: I, II, & III

A

C

83
Q

Rank the following in order of decreasing nucleophilicity in an aprotic solvent: RO-, RCOOH, ROH, HO-

A: RCOOH > ROH > RO- > HO-
B: HO- > ROH > RO > RCOOH
C: RO- > HO- > ROH > RCOOH
D: RCOOH > RO- > HO- > ROH

A

C

84
Q
A

D

85
Q
A

A

86
Q

Rank the following in order of decreasing oxidation state: amine, carboxylic acid, aldehyde, alkane

A: Aldehyde, amine, alkane, carboxylic acid
B: Carboxylic acid, aldehyde, amine, alkane
C: Carboxylic acid, amine, aldehyde, alkane
D: Alkane, amine, aldehyde, carboxylic acid

A

B

87
Q

The last step in the Grignard reaction is acidification, in which the alkoxide ion is protonated to form the final alcohol product. During this reaction, the alkoxide ion acts as a:
A: Lewis base only
B: Bronsted-Lowry base and Lewis base
C: Bronsted-Lowry base and Lewis acid
D: Bronsted-Lowry base only

A

B

88
Q

If 2-butanol was treated with dichromate, what reaction would occur
A: Reduction, resulting in the formation of butene
B: Oxidation, resulting in the formation of butanoic
C: oxidation, resulting in the formation of butanone
D: no reaction would occur

A

C

89
Q

If 1-hexanol was treated with pyridinium chlorochromate, what would the end product be?

A: 2-Hexanol
B: 2-Hexanone
C: hexanal
D: hexanoic

A

C

90
Q

Sn1 reactions show first-order kinetics because:

A: the rate-limiting step is the first step to occur in the reaction
B: the rate-limiting step involves only one molecule
C: there is only one rate-limiting step
D: the reaction involves only one molecule

A

B

91
Q

In a protic solvent, which of the following halogens would be the best nucleophile?

A: Br-
B: Cl-
C: F-
D: I-

A

D

92
Q
A

D

93
Q
A

A

94
Q
A

D

95
Q

Aldehydes are generally more reactive than equivalent ketones to nucleophiles. This is likely due to differences in:

A: steric hindrance
B: Leaving group ability
C: resonance stabilization
D: electron-withdrawing character

A

A

96
Q

Which conversion between carboxylic acid derivatives is NOT possible by nucleophilic reaction
A: carboxylic acid to ester
B: ester to carboxylic acid
C: anhydride to amide
D: Ester to anhydride

A

D

97
Q

Alcohols have higher boiling points than there analogous hydrocarbons because:

A: the oxygen atoms in alcohols have shorter bond lengths
B: hydrogen bonding is present in alcohols
C: alcohols ae more acidic than their analogous hydrocarbons
D: alcohols can be oxidized to ketones

A

B

98
Q

Tertiary alcohols are oxidized with difficulty because:

A: there is no hydrogen attached to the carbon with the hydroxyl group
B: there is no hydrogen attached to the alpha carbon of the carbonyl
C: tertiary alcohols contain hydroxyl groups with no polarization
D: they are relatively inert

A

A

99
Q
A

B

100
Q
A

B

101
Q

Which of the following correctly lists methanol, isobutyl alcohol, and propanol by decreasing boiling point?
A: Methanol, isobutyl alcohol, propanol
B: Isobutyl alcohol, methanol, propanol
C: Isobutyl alcohol, propanol, methanol
D: Methanol, propanol, isobutyl alcohol

A

C

102
Q

Which of the following correctly lists hexanol, phenol, and cyclohexanol by increasing acidity of the hydroxyl hydrogen?

A: phenol < hexanol < cyclohexanol
B: cyclohexanol < hexanol < phenol
C: cyclohexanol < phenol < hexanol
D: phenol, cyclohexanol < hexanol

A

B

103
Q
A

B

104
Q

Which of the following will convert cyclohexanol to cyclohexanone?
i. chromium trioxide
ii. pyridinium chlorochromate
iii. sodium dichromate

A: I
B: II
C: I & III
D: I, II, & III

A

D

105
Q

Successfully converting 3-phenylpropanol to 3-phenylpropanioc acid by the Jones oxidation requires the oxidizing agent, the solvent, and:

A: dilute sulfuric acid
B: dilute sodium hydroxide
C: anhydrous conditions
D: high temperature

A

A

106
Q

Treating 2-methyl-1-propanol with methylsulfonyl chloride in base, followed by reaction with pyridinium chlorochromate, and a final step in strong acid, will give an end product of:

A: 2-methyl-1-propanol
B: 2-methylpropanal
C: 2-methylpropanoic acid
D: 2-methyl-1-propane

A

A

107
Q

Reaction of 1-phenylethanone with ethylene glycol, also known as ethane-1,2-diol, in aqueous H2SO4 will result in the formation of:

A: a ketal
B: a carboxylic acid
C: an aldehyde
D: a hemiacetal

A

A

108
Q
A

D

109
Q

In order to convert phenols into hydroxyquinones, how many steps of oxidation or reduction are required?
A: 1 oxidation step
B: 2 oxidation step
C: 1 reduction step
D: 2 reduction steps

A

B

110
Q

The conversion of ubiquinone to ubiquinol requires what type of reaction?
A: condensation
B: oxidation
C: reduction
D: hydrolysis

A

C

111
Q
A

A

112
Q

All of the following are true with respect to carbonyls EXCEPT:
A: the carbonyl carbon is electrophilic
B: the carbonyl oxygen is electron-withdrawing
C: a resonance structure of the functional group places a positive change on the carbonyl carbon
D: the π electrons are mobile and are pulled toward the carbonyl carbon

A

D

113
Q

Order the following compounds by increasing boiling point: butane, butanol, butanone

A: butanol < butane < butanone
B: Butane < butanone < butanol
C: butanone < butane < butanol
D: Butane < butanol < butanone

A

B

114
Q
A

C

115
Q
A

A

116
Q
A

B

117
Q
A

B

118
Q
A

D

119
Q

Hemiacetals and hemiketals usually keep reacting to form acetals and ketals. Why is it difficult to isolate hemiacetals and hemiketals?

i. these molecules are unstable
ii. the hydroxyl group is rapidly protonated and lost as water under acidic conditions, leaving behind a reactive carbocation
iii. the molecules are extremely basic and react rapidly with one another

A: I
B: I & II
C: II & III
D: I, II, & III

A

B

120
Q

In a hemiacetal, the central carbon is bonded to:

A: -OH, -OR, -H, and -R
B: -H, -OR, -OR, and -R
C: -OH, -OR, -R, and -R
D: -OR, -OR, -R, and -R

A

A

121
Q

In a reaction between hydrogen cyanide, butyraldehyde, and ethylmethylketone, which compounds will come together to form the major product

A: Butyraldehyde and hydrogen cyanide
B: Ethylmethylketone and butyraldehyde
C: Hydrogen cyanide and ethylmethylketone
D: no reaction will occur

A

A

122
Q

Which of the following describe(s) pyridinium chlorochromate (PCC)?

i. an oxidant that can form aldehydes from primary alcohols
ii. an oxidant that can completely oxidize primary alcohols
iii. an oxidant that can completely oxidize secondary alcohols

A: I
B: I & II
C: I & III
D: I, II, & III

A

C

123
Q

To form a geminal diol, which of the following could attack a carbonyl carbon?

A: hydrogen peroxide
B: water
C: potassium dichromate
D: Ethanol

A

B

124
Q

In reaction between ammonia and glutaraldehyde, what is the major product

A: an imine
B: a cyanohydrin
C: a semicarbazone
D: A hydrazone

A

A

125
Q

Which of the following can be used to reduce a ketone to a secondary alcohol

A: CrO3
B: KMnO4
C: LiAIH4
D: Ag2O

A

C

126
Q

Imines naturally tautomerize to form:

A: oximes
B: hydrazones
C: semicarbazones
D: enamines

A

D

MCAT (6 decks)

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