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MCAT > Orgo 1/2 > Flashcards

Orgo 1/2 Flashcards

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1
Q

which are stronger? sigma or pi?

A

sigma bonds

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2
Q

define hybridized orbitals

A

combination of multiple types of orbitals at an intermediate energy levels

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3
Q

what shape is ammonium

A

tetrahedral

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4
Q

which of these is is a polar bond and why
A. C-C
B. C=C
C. C-O
D. C-H

A

C. C-O
it is the carbon bonded to a oxygen

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5
Q

true or false: breaking bonds requires energy

A

true

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6
Q

atoms usually want 8 electrons. what are the 4 exceptions to this rule?

A

H, He= they have S orbital so they only want 2
Boron and beryllium = want 6

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7
Q

in resonance, stable structures are _________ together/apart

A

closer together

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8
Q

define constitutional isomers

A

compounds that have the same chemical formula but have different atom to atom connectivity
think: constitution is written the same but connects to ppl differently

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9
Q

define diastereomers

A

2 compounds have different absolute stereochemistry at 1+, but not all stereocenters

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10
Q

is E2 a slow or fast reaction
what is formed/not formed

A

fast: no carbocation is formed, but alkene is formed

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11
Q

is SN1 a slow or fast reaction
what is the resulting formations

A

slow: carbocation is formed, 1 functional group is swapped for another

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12
Q

if boiling point is increased, what happened to the polarity

A

it increases

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13
Q

what is the most stable carbocation
primary
secondary
tertiary
quaternary

A

tertiary
quaternary is not a real thing

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14
Q

which of theses is not an oxidizing agent
LiAlH4
O3
Cr2O7
KMnO4

A

LiAlH4
the rest have Os

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15
Q

what do you think when you see a vic-diol functional group?

A

a ring with neighboring attachments (different point but right next to each other)
think: in spanish neighbors is vecin

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16
Q

what do you think when you see a gem-diol functional group?

A

a ring with 2 attachments on the same point
think: the ring looks like a ring with a gem

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17
Q

when a pi bond is present a _______ bond is also present

A

sigma

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18
Q

in terms of strength, rotation, stability, and reactiveness, describe the difference between sigma bonds and pi bonds

A

sigma: stronger, allow rotation, more stable, and less reactive
pi: weaker, prevent rotation, less stable, more reactive

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19
Q

what is hybridization

A

bonded atoms will create hybridized orbitals that are at an intermediate energy level

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20
Q

how does energy come into play when it comes to forming and breaking bonds

A

when a bond is broken, energy is required
when a bond is formed, energy is released

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21
Q

more stable molecules have a (greater/smaller) heat of combustion
less stable molecules have a (smaller/greater) heat of combustion

A

more stable: smaller heat of combustion
less stable: greater heat of combustion

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22
Q

what is the octet rule

A

atoms in the first two rows have a propensity to gain/lose electrons to fill a valence shell of 8

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23
Q

what are the three rules of stability, in order of importance

A

the most stable structure
1. allows the most atoms to have a full octet
2. has the fewest amount of formal charges
3. if there are charges, has them closer together

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24
Q

what is an isomer

A

two or more molecules with the same molecular formula but different bonding patterns

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25
Q

conformational isomer

A

compounds that only differ due to rotation about a single bond
not true isomer!

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26
Q

structural isomer

A

compounds that differ in bond to bond connectivity

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27
Q

stereoisomer

A

compounds that differ only only in 3D arrangement of their atoms

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28
Q

what is a stereocenter

A

any carbon that has 4 different groups bonded to it

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29
Q

what is the definition of chiral

A

any molecule with one or more stereocenters

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30
Q

enantiomers

A

2 compounds with different absolute configuration at every stereocenter
(mirror images)

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31
Q

dextrorotatory vs levorotatory

A

D: when compounds rotate light clockwise(think to write a D you need to draw clockwise)
L: when compounds rotate light counterclockwise

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32
Q

what is more stable: cis or trans

A

cis

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33
Q

what is a meso compound

A

molecules containing 2+ chiral centers containing a plane of symmetry
this symmetry cancels out any optical activity

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34
Q

how many steps do E1/E2 have?
Sn1/Sn2?

A

E1: 2
E2: 1
SN1: 2
SN2: 1

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35
Q

what is a carbonyl functional group

A

any carbon double bonded to an oxygen

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36
Q

what is the purpose of extraction

A

separates aqueous and organic layers

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37
Q

if you are given 2 benzene rings to extract, where will the benzene rings end up and why?

A

in the organic layer: 2 benzene rings are 2 hexagons(with lines in the middle) connected by 1 line
they have no polar properties because it is all bonded by C-H bonds. so it would end up in the organic layer

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38
Q

in extraction, what kind of molecules would go to organic?
what would do to aqueous?

A

polar and hydrophilic would do aqueous
nonpolar and hydrophobic would go to organic

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39
Q

what does distillation do

A

separates compounds based on boiling points

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40
Q

what determines boiling points? how does that work in terms of stronger and weaker?

A

INTERmolecular forces
lower intermolecular forces means lower boiling points

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41
Q

for example, if you were given a benzene ring and a water molecule, which would have the higher boiling point

A

since boiling point is based on intermolecular forces, figure out which one has more/stronger
benzene: VanderWaals (also has hydrophobic interactions bc of the C-H bonds)
water: VanderWaals, hydrogen bonding, Dipole-Dipole
this would mean that water would have the higher boiling point

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42
Q

what is chromatography?
what are 2 common approaches

A

using molecular interactions to separate compounds
1. gas chromatography
2. liquid chromatography

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43
Q

what are the 2 phases in chromatography and what are their characteristics

A

stationary: doesn’t move, nonpolar
mobile: passes through stationary, polar

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44
Q

what happens if a polar molecule is put in to gas chromatography

A

since it is polar, it would travel more closely with the polar mobile phase
this means it elutes more quickly in gas chromatography

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45
Q

what are the two kinds of spectroscopy?

A

IR and HNMR

46
Q

what is the known as the ‘fingerprint’ region in IR spectroscopy?

A

500-1000

47
Q

what is the range for C=O in IR spectroscopy
sharp or broad?

A

1650-1800
sharp/narrow

48
Q

what is the range for C triple bonded to N or C triple bonded to C in IR spectroscopy?
sharp or broad?

A

2100-2260 sharp/narrow

49
Q

what is the range for C-H in IR spectroscopy?
sharp or broad?

A

2850-3100 sharp

50
Q

what is the range for O-H in IR spectroscopy?
sharp or broad?

A

3200-3400 broad

51
Q

what is the range for alkyne C-H in IR spectroscopy?
sharp or broad?

A

3300 sharp

52
Q

what is the range for N-H in IR spectroscopy?
sharp or broad?

A

3300-3500 sharp

53
Q

what does UV spectroscopy do?

A

shows absorbance due to double or triple bonds and conjugated systems
the higher the nm, the greater degree of conjugation

54
Q

in NMR spectroscopy, what is the ppm for H and C

A

1H: 0-12ppm
13C: 0.220ppm

55
Q

in extraction, how can the separation be improved?

A

add acid/base to add/remove charge
repeat process multiple times

56
Q

in extraction, how can the separation be messed up?

A

vigorous mixing
solvents that will react with the solute
solvents with high boiling point

57
Q

what happens during vacuum filtration

A

air is sucked out of the bottom flask to increase filtration rate

58
Q

what happens in recrystallization

A

impure product is dissolved into solvent, the solution is heated to melt the product, then is cooled and more pure solvent is solidified

59
Q

what is an amine

A

any organic molecule with a basic nitrogen atom

60
Q

what are the characteristics of amines? how do they act

A

they act as bases (function of thermodynamics) or nucleophiles (function of kinetics)

61
Q

what is a formal charge

A

valance minus electrons surrounding atoms

62
Q

how many valence electrons in C

A

4

63
Q

how many valence electrons in N

A

5

64
Q

how many valence electrons in O

A

6

65
Q

how many valence electrons in F

A

7

66
Q

alkane

A

/\/

67
Q

alkene

A

/\/

68
Q

alkyne

A

\///

69
Q

alcohol

A

OH
/\/

70
Q

ketone

A

…O
||
/\/\

71
Q

ether

A

/\/O\/

72
Q

what is the difference between R and S when it comes to stereochemistry

A

R is clockwise (the way you write it)
S is counterclockwise

73
Q

enantiomers

A

2 compounds with different absolute configuration at every stereocenter

74
Q

absolute stereochemistry

A

at any chiral carbon, if the priority of the groups proceeds clockwise the absolute stereochemistry is R. if the priority proceeds counterclockwise, the absolute stereochemistry is S

75
Q

what are the qualities of a base?
does it accept or reject protons?
is it electron dense or not?
what kind of charge does it have?
the stronger the base, does the product become more stable or less?

A

accept protons
electron dense
negatively charged
strongest base forms the most stable product

76
Q

what are the qualities of nucleophiles?
what does it attack?
is it electron dense or not?
what kind of charge does it have?
how does the speed come into play?

A

attacks electrophiles
electron dense
negatively charged
strongest nucleophile attacks the fastest

77
Q

what qualities does an electrophile have?
charge?
electron dense?

A

positively charged
electron poor

78
Q

compare and contrast E1/E2
steps
speed
carbocation formation
product stereochem
favored by

A

E1:
2 steps
slow speed
yes to carbocation formation
planar product stereochem
favored by weak bases
E2:
1 step
fast speed
no to carbocation formation
planar product stereochem
favored by strong bases

79
Q

compare and contrast Sn1/Sn2
steps
speed
carbocation formation
product stereochem
favored by

A

Sn1:
2 steps
slow speed
yes to carbocation formation
racemic mixture product stereochem
favored by weak nucleophile
Sn2:
1 step
fast speed
no carbocation formation
inversion product stereochem
favored by strong nucleophile

80
Q

what are radicals

A

they are dangerous and can cause DNA damage

81
Q

are alkenes nucleo or electro philes?
why?

A

nucleophiles
electrons in a pi bond attack electrophile, leaving a carbocation (electrophile), which is then attacked by the nucleophile

82
Q

the more substituents an alkene has, the (more/less) stable it is

A

more stable

83
Q

alkynes have how many bonds?

A

triple

84
Q

what defines an alcohol

A

-OH functional group

85
Q

what is a benzene

A

hexagon, with the 3 lines inside it

86
Q

boiling point (increases/decreases) with (increased/decreased) molecular weight and (increases/decreases) with more branching

A

boiling point increases with increased molecular weight and decreases with more branching

87
Q

hydrogen bonding donors and acceptor

A

anything with an -OH or -NH can be a hydrogen bond donor
anything with an -O,-N,-F is hydrogen bond acceptor

88
Q

alcohols have (higher/lower) melting & boiling points and (higher/lower) stability due to the presence of hydrogen bonds

A

alcohols have higher melting & boiling points and higher stability

89
Q

are alcohols more or less acidic than water

A

less acidic than water

90
Q

what are some oxidizing agents

A

O3, Cr2O7, CrO4, KmnO4, Jones reagent, Collins reagent, PCC, PDC

91
Q

what are the reducing agents (classify weak and strong)

A

weak: NaBH4
strong: LiAlH4, H2/Pressure

92
Q

why are grignard synthesis important?

A

important because they allow us to add carbons to a chain

93
Q

how does polarity and electronegativity go together?

A

larger the difference in electronegativity, the more polar a bond

94
Q

which is more polar?
C-O
C-F

A

C-O is less polar
C-F is more polar

95
Q

what does a compound have to do to be considered an acid, in terms of a charge

A

either a partial or full positive charge

96
Q

what does a compound have to do to be considered an base or nucleophile, in terms of a charge

A

either a partial or a full negative charge

97
Q

how does charge relate to electronegativity

A

more electronegative: partial negative charge
less electronegative: partial positive charge

98
Q

how does charge relate to the withdrawing/donating of electrons?

A

full/partial positive: withdraw
full/partial negative: donate

99
Q

H donates or withdraws electrons?
alkanes donates or withdraws electrons?
alkenes donates or withdraws electrons?

A

H does neither
alkanes donate
alkenes withdraw

100
Q

the (more/less) the conjugate base, the (stronger/weaker) the acid

A

the more stable the conjugate base, the stronger the acid

101
Q

how does acidity and basicity relate to electron withdrawing/donating groups

A

withdrawing: increase compounds acidity
donating: increase compounds basicity

102
Q

do electron donating/withdrawing groups affect the stability of a compound?

A

yes

103
Q

carbocations are more or less stable with more substituents?

A

more

104
Q

are cyclic ethers highly reactive? if so why?

A

yes, due to their extreme ring strain

105
Q

what is an ether

A

oxygen bonded to 2 are groups

106
Q

The stereochemical designators α and β distinguish between

A

epimers at anomeric carbon atom

the a/B distinguish between molecules with multiple chiral centers
these molecules differ only in the configuration of the site, anomeric carbon atom

107
Q

which is more chiral
alpha or beta carbons

A

alpha

108
Q

are carbonyl carbons achrial or chiral?

A

achiral

109
Q

what do you do when asked to find out how many stereoisomers a “compound” has?

A

count the chiral centers = n
2^n

110
Q

when finding discrete signals on a proton NMR spectrum, what do you do

A

look at the compound given to you, then find the carbons. if the carbons are the same, they count as 1 kind of carbons; if they are different then they act as different one

111
Q

which of these is the least reactive?
ethanol
diethyl ether
dichloromethane
acetone

A

diethyl ether

112
Q

hydrophobic interaction chromatography relies one high or low salt concentrations

A

high salt concentrations

MCAT (13 decks)

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