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Catz > MCAT ORGANIC Chem > Flashcards

MCAT ORGANIC Chem Flashcards

1
Q

Does the term allotrope refer to elements, compounds, or both?

A

only Elements

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2
Q

Are liquid water and water vapor 2 allotropes of H2O?

A

No.

Allotropes refer to different forms of an element IN THE SAME PHASE

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3
Q

What kind of hybridization holds the carbon atoms together in graphite?

A

sp2

(p 428, Barrons)

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4
Q

What does the term isomerism mean in chemistry?

A

Ability of atoms to arrange themselves in more than 1 way to give different compounds that have the same molecular formula (Nassau chem text by brady & senese)

atoms → different combinations → different compounds → same molecular formula

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5
Q

What is the name/term for compounds with the same molecular formula, but with atoms connected in a different order, and thus have different properties?

A

constitutional isomers

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6
Q

What’s another name for a constitutional isomer?

A

Structural isomer

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7
Q

What’s the other variety of isomer, besides structural isomers?

A

Stereoisomers

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8
Q

What is a stereoisomer?

A

molecules that have the same molecular formula, and have the same connections between the atoms, but have a DIFFERENT SPATIAL ORIENTATION

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9
Q

What does it mean to have the prefix n- in a molecule’s name?

A

n- stands for normal. This means that the molecule’s spine/longest carbon chain is a straight chain

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10
Q

What does trans- mean?

A

The groups attached to the double bonded carbons are on opposite sides.

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11
Q

Which isomer gives a straighter-looking molecule? Cis- or trans-?

A

Trans- isomers

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12
Q

True/False:

Cis- and trans- isomers have different chemical and physical properties

A

tru

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13
Q

Are your hands superimposable?

A

no

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14
Q

What is chirality?

A

“Handedness”. ‘

If one object is the mirror image of another object, AND if they are NOT superimposable, then these 2 objects are chiral.

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15
Q

What makes something organic?

A

A compound is organic if its molecules contain carbon.

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16
Q

Name 7 types/classes/groups of carbon-containing molecules that are NOT considered to be “organic.”

A

pure carbon and its allotropes,

CO2,

CO,

carbonates,

carbides,

cyanides,

thiocyanates, etc.

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17
Q

generally, organic compounds are held together by _____ bonds

A

covalent

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18
Q

CnH2n-2 is the general formula for which class of hydrocarbons?

A

alkynes

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19
Q

What is the general algebraic formula for alkanes?

A

CnH2n+2

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20
Q

What is the general formula for alkenes?

A

CnH2n

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21
Q

what is the symbol for acidity constant?

A

Ka

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22
Q

what’s another name/term for acidity constant?

A

Acid dissociation constant

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23
Q

The (stronger/weaker) the acid, the (higher/lower) the Ka.

A

stronger

higher

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24
Q

What is the relationship between Ka and pKa? (Hint: give the equation)

A

pKa =

  • log Ka
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25
Q

A (stronger/weaker) acid has a (higher/lower) pKa.

A

Sronger;

lower

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26
Q

A strong acid yields a (strong/weak) conjugate base.

(p 46, McMurry)

A

weak

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27
Q

In electrostatic potential maps of molecules, what color is the more positively-charged region(s) of the molecule?

A

blue

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28
Q

_______ have a carbon bonded to a halogen

A

haloalkanes

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29
Q

What’s the other term for haloalkanes?

A

Alkyl halides

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30
Q

_____ have 2 carbon atoms bonded to the same oxygen

A

ethers

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31
Q

______ have a C bonded to an N, and that same C is not double-bonded to an O

A

amines

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32
Q

_____ have a C bonded to an –SH group

A

thiols

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33
Q

______ have 2 Carbon atoms bonded to the same sulfur

A

sulfides

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34
Q

T or F:

in functional groups, the bonds are polar

A

tru

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35
Q

in functional groups, the C has a partial ____ charge

A

positive

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36
Q

what is the suffix for an alcohol?

A

-ol

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37
Q

what is the suffix for an ether?

A

Ether. The word ether, by itself.

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38
Q

what is the suffix for an amine?

A

-amine

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39
Q

what is the suffix for a nitrile?

A

-nitrile

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40
Q

what is the suffix for a nitro?

A

there is none.

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41
Q

_______ a C that is both double-bonded to an O and also bonded to an N

A

amide

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42
Q

what is the suffix for an aldehyde?

A

-al

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43
Q

what is the suffix for a ketone?

A

-one

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44
Q

what’s another name for “straight-chain” alkanes? I.e., straight-chain alkanes are also known as _________ alkanes

A

“Normal” alkanes

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45
Q

when talking about alkyl groups, a primary carbon is bonded to ______ other carbon(s)

A

1

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46
Q

if an alcohol’s –OH functional group is attached to a carbon–that is itself attached to one other carbon–then that alcohol is called a [primary/secondary/tertiary/quaternary] alcohol

A

primary

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47
Q

generally, the symbol/letter R stands for

A

the rest of the molecule

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48
Q

the old-school, non-IUPAC name for alkanes was ______ ?

A

paraffins

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49
Q

alkanes are chemically (reactive/inert) to most laboratory reagents

A

inert

(p 86)

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50
Q

with alkanes, boiling point and melting point show (regular / irregular) increases with increasing molecular weight

A

regular

(p 87)

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51
Q

what causes the proportional, or direct or “regular”, increase in both the boiling point and melting point of alkanes?

A

London dispersion forces amongst the molecules, the intensity of which force increases with increasing molecular size of the alkanes

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52
Q

What effect does branching have on alkanes that have the same # of C atoms?

A

The more branching there is, the lower the boiling point

(mcmurry p 88)

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53
Q

Why is there an inverse relationship between the level of branching and the boiling point of alkanes?

A

Branched alkanes have smaller surface area, and thus smaller London dispersion forces

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54
Q

What’s the word used to describe hydrocarbons that are NOT aromatic?

A

aliphatic

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55
Q

T or F:

aliphatic compounds do not contain rings.

A

False.

“Aliphatic” refers to hydrocarbons that are not aromatic. But not all ring-compounds are aromatic.

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56
Q

in organic chem, what does the word aryl mean?

A

Refers to any functional group or substituent that has a simple aromatic ring

(wikipedia)

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57
Q

Given two isomers: if the isomers have different connections between the atoms, they are called “____________ isomers”

A

constitutional or structural isomers

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58
Q

What are enantiomers?

A

molecules that are Mirror-images of each other, but are not superimposable

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59
Q

What is meant by “conformation”?

A

the 3-dimensional shape of a molecule at any given instant

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60
Q

What is a chirality center?

A

An atom that is bonded to 4 different groups/substituents

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61
Q

What are conformation isomers? Describe/define it.

A

molecules that have the same molecular formula, and are just different arrangements of atoms that result from rotation around a single bond

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62
Q

What is torsional strain?

A

Strain in a molecule caused by electron repulsion between two segments (namely the H’s on opposite ends of the molecule) of the molecule that eclipse each other when the molecule is viewed thru the length of its spine

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63
Q

When talking about a molecule with a single bond, the lowest-energy, most stable conformation is the one in which all the H’s are [as far away from one another / as close to each other] as possible.

A

As far away from one another

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64
Q

The conformation of an ethane, at which all the hydrogens are as far away from each other as possible is called ___________

[choices are below as a hint]

hint: it’s either staggered or eclipsed

A

staggered

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65
Q

If torsional strain of an ethane molecule can be measured, what is its amount?

A

12 kJ/mol

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66
Q

How much is 12 kJ/mol in kcal/mol?

A

3kcal/mol

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67
Q

T or F:

conformational isomerism is a form of stereoisomerism in which the isomers can be interconverted by rotations about pi bonds

A

False.

Conformational isomers differ b/c of rotations around single, i.e. sigma, bonds

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68
Q

The anti conformation is the [lowest/highest] energy conformation of a butane

A

lowest

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69
Q

What is steric strain?

A

the repulsive interaction that occurs when atoms are forced closer together than their atomic radii allow

(mcmurry 107)

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70
Q

why are a lot of cycloalkanes not shaped like “flat” rings where all the C’s are all on the same plane?

A

The “puckered,” or irregular shape, of the cycloalkane gives it zero angle strain and zero torsional strain

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71
Q

With which alicyclic compound is the chair conformation seen?

A

Cyclohexane

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72
Q

Due to the chair conformation, there are 2 kinds of positions for substituents on the ring: _____ positions and _______ positions.

A

axial positions, and

equatorial positions

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73
Q

The substituents of cyclohexane that are in the ______ position are perpendicular to the ring (i.e., parallel to the ring axis)

A

axial

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74
Q

What is a conformer?

A

Another name for a conformational isomer

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75
Q

What’s another name for two or more conformational isomers that differ only b/c of a rotation around just 1 single bond?

A

rotamer

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76
Q

At any given instant, about ____ % of ethane molecules have a staggered conformation and only about ______ % are close to the eclipsed conformation

(mcmurry 104)

A

99

1

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77
Q

Another name for a chiral center or chirality center is __________

(Hint: 2 words)

A

stereogenic center

(berk review website)

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78
Q

Name the specific molecule/compound with which the term “chair conformation” is associated. I.e., what’s the molecule that comes to mind when you hear “chair conformation”?

A

cyclohexane

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79
Q

Besides the chair conformation, what other conformation(s) are possible with cyclohexanes? Name them.

A

Boat conformation

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80
Q

In a chair cyclohexane, what are the names of the two positions/orientations that the H atoms can have?

A

Axial and

equatorial

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81
Q

How many of the H atoms in a simple cyclohexane are in the axial position?

A

3

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82
Q

With monosubstituted cyclohexanes, a substituent is almost always more stable in an [equatorial/axial] position

A

equatorial

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83
Q

When you have a mixture of two isomers, which equation will allow you to calculate the percentage of each isomer in that mixture?

A

∆E = - RT ln K ← NOTE:
this eqn can be used if the mixture is at equilibrium

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84
Q

∆E = - RT ln K

What does R stand for in the equation given above?

A

Gas constant

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85
Q

What is the actual numerical value of R (don’t forget the units)?

A

8.315 J/(K∙mol)

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86
Q

Why is there a difference between the potential energy of a cyclohexane with an axial methyl group and the potential energy of a cyclohexane with an equatorial methyl group?

A

The energy difference is caused by steric strain between the methyl group and the other hydrogens

(p 120)

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87
Q

Why are 1,3-diaxial interactions so important? I.e., what are they responsible for?

A

This interactions results in the steric strain that is responsible for the energy difference between axial and equatorial conformers of a cyclohexane.

(mcmurry 120)

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88
Q

Which specific parts of a cyclohexane are involved in a 1,3-diaxial interaction?

A

The axial methyl group of a C1, and the H molecules of a C3 and C5

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89
Q

When talking about a trans-disubstituted cyclohexane, the two substituents are: (see choices below):

(a) both axial
(b) both equatorial
(c) one axial and the other equatorial

A

(a) or (b)

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90
Q

Which is the more stable conformation: boat or chair?

A

Chair

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91
Q

What does the word “polycyclic” mean?

A

Refers to compounds that contain two or more rings that are bonded together

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92
Q

What’s the difference between “polycyclic” and “heterocyclic”?

A

Heterocyclic refers to compounds having, as ring members, atoms of *at least two different elements *

(http://goldbook.iupac.org/H02798.html)

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93
Q

What’s the name of the reaction in which a single reactant undergoes a reorganization of bonds and atoms to yield an isomeric product?

A

Rearrangement rxn

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94
Q

What’s the name of a reaction in which 2 reactants add together to form a single new product with no atoms “left over”?

A

addition rxns

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95
Q

What’s the name of a rxn in which a single reactant splits into 2 products?

A

Elimination rxn

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96
Q

What’s the name of a rxn in which 2 reactants exchange parts to give 2 new products?

A

Substitution rxn

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97
Q

An overall description of a how a rxn occurs, is called a/an _________.

A

rxn mechanism

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98
Q

When a covalent bond breaks symmetrically so that 1 electron remains with each product fragment, the bond cleavage is called [homolytic/heterolytic].

A

Homolytic

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99
Q

If a covalent bond forms when both bonding electrons are donated by just 1 of the reactants, this type of bond making is called [homogenic/heterogenic] bond making.

A

Heterogenic

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100
Q

Radical rxns involve [symmetrical/asymmetrical] bond breaking and bond making

A

symmetrical

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101
Q

The opposite of ‘radical rxn’ is a ‘_____ rxn’

A

polar

102
Q

[Larger/smaller] atoms are more polarizable.

A

Larger

103
Q

Why are larger atoms more polarizable?

A

b/c their electrons are more loosely held than smaller atoms

104
Q

The electron-poor reactant is called an/a (Hint below)

Hint: ____phile

A

Electrophile

105
Q

True/false:

an electrophile may be either neutral or negatively charged

A

False.

Correct answer is, that an electrophile can be
either neutral or positively charged.

106
Q

Lewis bases are [nucleophiles/electrophiles].

A

Lewis bases are electron donors and behave as nucleophiles.

107
Q

another name for a carbon cation is _______.

A

carbocation

108
Q

True/false:

Carbocations can accept electron pairs

A

tru

109
Q

The word endergonic is associated with the [Δ** H / Δ G / Δ S]** of a rxns.

A

Δ G

110
Q

The fancy term for Δ G is ‘_________ change’

A

Gibbs free-energy change

111
Q

The fancy term for Δ H is ‘______ change’

A

enthalpy change

112
Q

What is the symbol for ‘bond dissociation energy’?

A

D

113
Q

Define bond dissociation energy

A

amount of energy required to break a given bond to produce 2 radical fragments when the molecule is in the gas phase at 25 degrees Celsius

114
Q

[Cis/trans] alkenes are more stable

A

trans

115
Q

Why are trans alkenes more stable?

A

b/c cis alkenes have steric strain between the 2 substituents that are on the same side of the double bond

116
Q

True or False:

the more substituted the alkene, the more stable it is.

A

true

117
Q

In Orgo, when you hear the word “attack” being used, which specific atom/molecule/particle is the “attacker”?

A

Electrons

118
Q

What is Markovnikov’s rule?

(Hint: not the one referring to carbocations)

A

In the addition of a given molecule ‘H-X’ to an alkene, the H atom bonds to the double-bonded carbon that has FEWER alkyl substituents connected to it.

The X attaches to the double bonded carbon that has MORE alkyl substituents.

119
Q

What’s Markovnikov’s rule when restated to include cations?

A

In the addition of H-X to an alkene, the more substituted carbocation is formed as the intermediate rather than the less highly substituted one.

120
Q

True or false:

the more substituted a carbocation is, the less stable it is.

A

False.

More highly substituted carbocations are more stable than less highly substituted ones.

121
Q

What’s the name of the stabilizing interaction between a vacant p orbital and a properly oriented neighboring C-H sigma orbital (mcmurry p. 191)?

A

Hyperconjugation

[is this really important for the MCAT??]

122
Q

What is an alkyl group?

A

An alkane that is missing one hydrogen

123
Q

What is the Hammond postulate?

A

Basically it states that we can get a picture of what given transition state looks like, by looking at the structure of the nearest stable species.

Thus exergonic rxns have transition states that resemble reactant;
endergonic rxns have transition states that resemble product.

124
Q

When an s and a p orbital combine to form a hybrid orbital, what is the total # of orbital(s) formed?

A

2

125
Q

What is the mathematical expression that tells u the number of hybrid orbitals on a given atom with a hybridization of ‘spx’?

A

1 + x

126
Q

1 + x is the eqn that tells u the number of hybrid orbitals on a given atom with a hybridization of ‘spx’.

What are all the potential numerical values of X in the above expression?

A

1, 2, or 3

127
Q

What expression tells you the percentage of the “s character” for any given orbital of spx?

A

1 / (1+x)

128
Q

What percentage of an sp2 orbital has the p character?

A

67%

[use the formula x/1+x]

129
Q

If a given atom in a molecule has a sum of 2 attached atoms and lone electron pairs, what is its hybridization?

A

sp

130
Q

If a given atom in a molecule has a sum of 4 attached atoms and lone electron pairs, what is its hybridization?

A

sp3

131
Q

What molecular geometry does an sp hybridization have?

A

Linear

132
Q

What is the bond angle for an sp2 hybridization?

A

120

133
Q

What is the bond angle for an sp3 hybridization?

A

109.5 degrees

134
Q

T or F:

a saturated molecule contains pi bonds

A

false

135
Q

What expression shows how many H atoms are present in a saturated compound that has n carbon atoms?

A

2n + 2

136
Q

A _____-bond is formed by the parallel, side-to-side alignment of 2 unhybridized p orbitals on adjacent atoms.

A

π

137
Q

What is bond dissociation energy?

A

The energy required to break a bond homolytically

138
Q

When a bond is broken and both electrons go to just one of the resulting fragments, this kind of bond-breaking or bond-cleavage is called _______ (adjective)

A

heterolytic

139
Q

Which type of bond cleavage results in the formation of two radicals?

A

Homolytic

140
Q

When comparing the same type of bonds, the greater the s character in the bonding orbitals, the [longer/shorter] the bond

A

shorter

(p 452, TPRH bio)

141
Q

Which bond would you expect to be shorter: an sp-s bond, or an sp3-s bond?

A

sp-s bond is shorter

142
Q

Another name for a chiral center or stereogenic center is _______

A

stereocenter

143
Q

What exactly is a chiral center?

A

An atom that has 4 different groups bonded to it.

144
Q

In Orgo, a chiral center is usually which element?

A

carbon

145
Q

What are enantiomers?

A

Isomers that are mirror images of each other AND are chiral.

146
Q

What is the name for stereoisomers that are not mirror images?

(I.e., the overall name for the entire category, not just a specific subtype or variety)

A

diastereomer

147
Q

T or F:

cis-trans isomers are a type of enantiomer

A

False.

Cis-trans isomers fall under the category of Diastereomers

148
Q

Do enantiomeric pairs have differences in melting point?

A

no

149
Q

Do enantiomeric pairs have differences in boiling point?

A

no

150
Q

Do enantiomeric pairs have differences in dipole moment?

A

No (p 462, TPRH bio)

151
Q

Do enantiomers have differences in their optical activity?

A

yes

152
Q

What mathematical expression tells us how many stereoisomers a molecule can possibly have if it has n chiral centers?

A

2n

153
Q

Can a molecule with n chiral centers have more than 2n stereoisomers?

A

no

154
Q

Can a molecule with n chiral centers have less than 2n stereoisomers?

A

yes

155
Q

What is a meso compound?

A

Molecule that has at least 1 chirality center, but has a plane of symmetry and thus is achiral

156
Q

What are epimers?

A

Diastereomers that differ in their absolute configuration at ONLY ONE chiral center

157
Q

For naming alkenes, the cis-trans naming convention only works with ____-substituted alkenes. (possible answer choices below)

Choices: mono-, di-, tri-, tetra-

A

di

158
Q

What’s the name of the naming system developed for alkenes that are trisubstituted and tetrasubstituted?

A

E,Z system

159
Q

What is ‘absolute configuration’?

A

the exact 3-dimensional structure of a chiral molecule

160
Q

What set of rules are used to determine a molecule’s absolute configuration?

A

the Cahn-Ingold-Prelog rules

161
Q

Epimers that form as a result of ring closure are known as ______

A

anomers

162
Q

What specific type of organic molecules will you see the term ‘anomer’ associated with?

A

Sugars (saccharides)

163
Q

Glucose in its ring form is called ___

A

glucopyranose

164
Q

What are geometric isomers?

A

Diastereomers that differ in the orientation of substituents around a ring or a double bond

165
Q

Name 2 types of geometric isomers commonly encountered in Orgo.

A

Cis-trans isomers; and

E,Z isomers

166
Q

Describe the relationship between a molecule’s optical activity and its absolute configuration.

A

There is no correlation between a molecule being dextrorotary/levorotary and it being R or S

167
Q

Hydrocarbons are generally nonpolar, yet can attract/repel each other to some extent.

Which force allows for these interactions among otherwise nonpolar molecules?

A

van der Waals forces, specifically London dispersion forces.

168
Q

Does branching have any effect on boiling point and melting point for hydrocarbons?

A

yes

169
Q

Branching [raises/lowers] the melting point of a hydrocarbon.

A

lowers

170
Q

Branching [raises/lowers] the boiling point of a hydrocarbon.

A

Lowers

171
Q

Increasing molecular weight [increases/decreases] MP of hydrocarbons.

A

increases

172
Q

Increasing molecular weight [increases/decreases] BP of hydrocarbons.

A

increases

173
Q

In organic chem, which structures/atoms/functional groups can function as hydrogen acceptors for a hydrogen-bond?

A

A lone pair of electrons on a nitrogen, an oxygen, or fluorine can accept an H an make a hydrogen bond

174
Q

Can the oxygen of a hydroxyl group function as an H-acceptor for a hydrogen bond?

A

YES

175
Q

In organic chem, which structures/atoms/functional groups can function as hydrogen donors for a hydrogen-bond?

A

An H that is attached to an N, an O, or an F, can fncn as a hydrogeon bond donor

176
Q

Given several molecules that contain oxygen, how do you rank them in order of increasing boiling point?

A

For each molecule, count the number of oxygens. Each oxygen equals one hydrogen-bond acceptor.

Count the number of Hydrogens that are bonded to an N, O, or F. These are hydrogen donors.

Order the molecules according to the sum of hydrogen acceptors and hydrogen donors.

177
Q

What does the solubility of a hydrocarbon depend on?

A

The polarity of the solute, and the polarity of the solvent.

178
Q

The dipole moment of a hydrocarbon is:

(a) very small to zero
(b) moderate to very large

A

very small to zero

179
Q

As a general rule, hydrocarbons containing [#] or fewer carbons have good solubility in water.

[What is the number?]

A

6

180
Q

Nucleophilicity [increases/decreases] going down the periodic table within a particular group

A

increases

181
Q

Chloride anion, hydroxyl group, ammonia, cyanide PAI, unattached hydroxyl PAI, ethane are examples of [nucleophiles/electrophiles]

A

nucleophiles

182
Q

Nucleophilicity [increases/decreases] as electronegativity decreases.

A

Increases

183
Q

What are electrophiles?

[TPRH has an excellent definition on p 478]

A

species that have a positive or partial positive charge and, frequently, have in incomplete octet

184
Q

Electrophilicity [increases/decreases] as negative charge increases

A

decreases

185
Q

Carbonium ions are also called __________.

A

carbocations

186
Q

Most organic rxns proceed thru one of these 3 types of intermediate species:

A

carbocations;

alkyl radicals; or

carbanions

187
Q

on the MCAT, __________ will always be sp2 hybridized with an empty p orbital

A

carbocations

188
Q

on the MCAT, alkyl radicals will be ___ hybridized with the unpaired electrons in an unhybridized ___ orbital.

A
  • sp*2;
  • p*
189
Q

What are alkyl radicals?

A

Rxn intermediates that contain 1 unpaired electron

190
Q

Regarding the 3 rxn intermediates: the less substituted a/an _________ is, the more stable it is.

A

carbanion

191
Q

What is a relationship between the reactivity of an alkyl radical and its degree of substitution?

A

The more substituted the alkyl radical is, the less reactive it is.

192
Q

What is the relationship between the reactivity of a carbocation and its degree of substitution?

A

The more substituted the carbocation is, the less reactive it is.

193
Q

What is the relationship between a carbanion’s reactivity and its degree of substitution?

A

The more substituted a carbanion is, the more reactive it is.

194
Q

What is the relationship between an alkyl radical’s energy and its degree of substitution?

A

The higher the alkyl radical’s energy, the less substituted it is.

195
Q

What is the relationship between a carbanion’s level of substitution and its energy?

A

The more substituted the carbanion is, the higher its energy

196
Q

What are 4 common examples of electrophiles according to TPRH p. 478?

A

Hydrogen ion,

carbon that is double-bonded to oxygen,

carbocation, and

borane

197
Q

what is the molecular formula of borane?

A

BH3

198
Q

Generally, the major product of a rxn is derived from the [most/least] stable intermediate.

(p 479, TPRH)

A

MOST

199
Q

What are the two major ways by which organic intermediates are stabilized?

A

Inductive effects, and

resonance effects

200
Q

Functional groups or substituents that surround a reaction intermediate will pull electrons towards them (i.e., away from the intermediate) if they are [more/less] electronegative than the intermediate.

A

If the substituent is MORE electronegative than the intermediate

201
Q

on the MCAT, alkyl substituents always [donate/withdraw] electrons to/from the rxn intermediate

A

donate electrons to the intermediate

[p 479; TPRH]

202
Q

Name the electron-deficient intermediate(s) found in orgo.

A

Carbocations, and

radicals

203
Q

Define the ‘inductive effect’

A

the stabilization of reaction intermediates by the sharing of electrons thru sigma bonds

204
Q

What does it mean to say that an electron is localized?

A

‘localized’ means it is confined to one orbital, which can be either

a bonding orbital between 2 atoms, or

a lone-pair orbital

205
Q

Resonance structures usually involve electrons that are adjacent to (i.e., 1 atom away from) a/an:

A

pi bond or an unhybridized p orbital

(p 485, TPRH)

206
Q

What tells you that a resonance structure can NOT be drawn for a particular atom?

A

If the atom is sp3 hybridized, it cannot appear in resonance forms

207
Q

A Bronsted-Lowry acid [donates/accepts] a ________

A

donates a proton

208
Q

The hybridization of a triple bond (e.g., alkYnes) is [sp / sp2 / sp3].

A

sp

209
Q

The most stable type of bond between atoms is [sigma / pi].

A

sigma

210
Q

What does conjugation mean, in Orgo?

A

Alternating single and double bonds.

211
Q

In organic chemistry, what does the term geminal mean?

A

refers to the relationship between two atoms or functional groups that are attached to the same atom

212
Q

The [smaller / larger] the molecular weight, the [higher / lower] the density.

A

The ↓↓ the molecular WEIGHT, the ↓↓ the density.

213
Q

Combustion reactions are [endothermic / exothermic / nonspontaneous].

A

EXOthermic

214
Q

(1) The most stable cycloalkane has [#] carbons.
(2) The second most stable cycloalkane has [#] carbons.

A

6

5

215
Q

In a radical reaction that has an Initiation, Propagation, and Termination steps, which of these steps feature homolytic bond cleavage?

A

Only the Initiation step has homolytic bond cleavage.

216
Q

Order the Halogen radicals from MOST reactive to LEAST reactive.

A

F > Cl > Br > I

217
Q

Which of the following is/are required for the Hydrogenation of an alkEne?

[Metal catalyst / high temperature / both / neither]

A

metal catalyst

218
Q

T/F:

When an alkEne reacts with an hydrogen halide (H-X), but in the presence of peroxide, the resulting alkyl halide product will be anti-Markovnikov.

A

partially True.

The anti-Markovnikov effect, created by the presence of peroxide, only works with H**Br **reactants, and NOT with reactions that have HCl or HI as reactants.

219
Q

When an alkEne reacts with an hydrogen bromide (HBr), but in the presence of peroxide, the resulting alkyl halide product will be anti-______.

A

Markovnikov

220
Q

When an alkEne reacts with a hydrogen bromide (HBr), but in the presence of a _______, the resulting alkyl halide will be anti-Markovnikov.

A

peroxide

221
Q

In an oxymercuration-demercuration reaction, the alcohol product that is formed is [Markovnikov / anti-Markovnikov].

A

Markovnikov

222
Q

Are rearrangements (i.e., switiching Hydrogens or Methyl groups around) possible in an **oxymercuration-demercuration **reaction?

A

No

223
Q

In hydroboration-oxidation reactions, the alcohol product is formed from the [syn / anti] addition, of an -OH and an H, to an alkene.

A

syn

224
Q

In the hydrogenation of alkenes using a metal catalyst, the Hydrogens are added to the alkene in a **[syn / anti] **addition.

A

syn

225
Q

EMR in the infrared (IR) range has a wavelength from ___ to ___ millimeters.

A

2.5 to 20 mm

226
Q

In IR spectroscopy, what is wavenumber?

A

the reciprocal (inverse) of the wavelength at which the organic molecule’s covalent bonds will vibrate

227
Q

In IR spectroscopy, wavenumbers are measured in this unit:

A

reciprocal centimeters (cm-1)

228
Q

In a IR spectroscopy graph, what are the labels of the axes?

A

Y-axis: Transmittance

X-axis: Wavenumber

229
Q

In IR spectroscopy, the carbonyl“stretch” is centered around what wavenumber?

A

1700 cm-1

230
Q

In IR spectroscopy, the “stretch” for the alkene double bond is centered around what wavenumber?

A

1650

231
Q

In IR spectroscopy, the triple bond“stretch” is centered around what wavenumber?

A

2600 - 2100

232
Q

In IR spectroscopy, describe the -OH“stretch”:

A

very steep, and very broad

3600 - 3200

233
Q

In IR spectroscopy, how do we tell apart the “stretch” of a aliphatic C-H bond, versus an aromatic C-H bond?

A
  • aliphatic C-H bonds stretch at a little less than 3000;
  • aromatic C-H bonds stretch at wavenumbers slightly greater than 3000
234
Q

In IR spectroscopy, the “stretch” wavelength for any kind of C-H bond is around:

A

3300 - 2850

235
Q

In IR spectroscopy, how do we distinguish the “stretch” of different types of C-H bonds?

A
  • for sp3 carbons, the stretch is around 3000 to 2850
  • for sp2 carbons, the stretch is around 3150 to 3000
  • for sp carbons, the stretch is around 3300
236
Q

What does shift or chemical shift mean when talking about NMR spectroscopy?

A

the location of the sets of peaks in the NMR spectrum

237
Q

For hydrogen NMR spectroscopy, along which numerical value(s) on the X-axis will you find halogens?

A

3 - 5

238
Q

For proton NMR spectroscopy, along which numerical value(s) will you find aromatics?

A

7

239
Q

For proton NMR spectroscopy, along which numerical value(s) will you find carboxyl groups?

A

10 - 12

240
Q

For proton NMR spectroscopy, along which numerical value(s) will you find aldehydes?

A

9 - 11

241
Q

For hydrogen NMR spectroscopy, along which numerical value(s) on the X-axis will you find alkyne triple bonds?

A

~ 2

242
Q

For hydrogen NMR spectroscopy, along which numerical value(s) on the X-axis will you find ketones?

A

1 - 2

243
Q

For hydrogen NMR spectroscopy, along which numerical value(s) on the X-axis will you find **benzyl **groups?

A

~ 3

244
Q

Which of the following cycloalkanes has the lowest heat of combustion, per —CH2— (i.e., methylene) group?

  • cyclopropane
  • cyclobutane
  • cyclohexane
  • cycloheptane
A

cyclohexane

245
Q

The Iodoform Test is used for:

A

to detect the presence of a carbonyl group with a methyl group bonded to it. E.g., methyl ketones, and acetaldehyde will give a positive Iodoform test.

246
Q

How do you know you have a positive Iodoform test?

A

The formation of a **yellow precipitate **

247
Q

Organic (i.e., carboxylic) Acid + Alcohol → ????

A

→ ESTER + water

248
Q

Alcohol + \_????_ → Ester + H20

A

organic (i.e., carboxylic) Acid

249
Q

A saponification rxn involves reacting a ____ with a ____.

A
  • inorganic base (e.g., NaOH);
  • ester
250
Q

Ester + inorganic Base → ????

A

→ Soap + alcohol

Catz (7 decks)

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