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Orgo 1/2 Flashcards

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
conformational isomer
compounds that only differ due to rotation about a single bond not true isomer!
26
structural isomer
compounds that differ in bond to bond connectivity
27
stereoisomer
compounds that differ only only in 3D arrangement of their atoms
28
what is a stereocenter
any carbon that has 4 different groups bonded to it
29
what is the definition of chiral
any molecule with one or more stereocenters
30
enantiomers
2 compounds with different absolute configuration at every stereocenter (mirror images)
31
dextrorotatory vs levorotatory
D: when compounds rotate light clockwise(think to write a D you need to draw clockwise) L: when compounds rotate light counterclockwise
32
what is more stable: cis or trans
cis
33
what is a meso compound
molecules containing 2+ chiral centers containing a plane of symmetry this symmetry cancels out any optical activity
34
how many steps do E1/E2 have? Sn1/Sn2?
E1: 2 E2: 1 SN1: 2 SN2: 1
35
what is a carbonyl functional group
any carbon double bonded to an oxygen
36
what is the purpose of extraction
separates aqueous and organic layers
37
if you are given 2 benzene rings to extract, where will the benzene rings end up and why?
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
38
in extraction, what kind of molecules would go to organic? what would do to aqueous?
polar and hydrophilic would do aqueous nonpolar and hydrophobic would go to organic
39
what does distillation do
separates compounds based on boiling points
40
what determines boiling points? how does that work in terms of stronger and weaker?
INTERmolecular forces lower intermolecular forces means lower boiling points
41
for example, if you were given a benzene ring and a water molecule, which would have the higher boiling point
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
42
what is chromatography? what are 2 common approaches
using molecular interactions to separate compounds 1. gas chromatography 2. liquid chromatography
43
what are the 2 phases in chromatography and what are their characteristics
stationary: doesn't move, nonpolar mobile: passes through stationary, polar
44
what happens if a polar molecule is put in to gas chromatography
since it is polar, it would travel more closely with the polar mobile phase this means it elutes more quickly in gas chromatography
45
what are the two kinds of spectroscopy?
IR and HNMR
46
what is the known as the 'fingerprint' region in IR spectroscopy?
500-1000
47
what is the range for C=O in IR spectroscopy sharp or broad?
1650-1800 sharp/narrow
48
what is the range for C triple bonded to N or C triple bonded to C in IR spectroscopy? sharp or broad?
2100-2260 sharp/narrow
49
what is the range for C-H in IR spectroscopy? sharp or broad?
2850-3100 sharp
50
what is the range for O-H in IR spectroscopy? sharp or broad?
3200-3400 broad
51
what is the range for alkyne C-H in IR spectroscopy? sharp or broad?
3300 sharp
52
what is the range for N-H in IR spectroscopy? sharp or broad?
3300-3500 sharp
53
what does UV spectroscopy do?
shows absorbance due to double or triple bonds and conjugated systems the higher the nm, the greater degree of conjugation
54
in NMR spectroscopy, what is the ppm for H and C
1H: 0-12ppm 13C: 0.220ppm
55
in extraction, how can the separation be improved?
add acid/base to add/remove charge repeat process multiple times
56
in extraction, how can the separation be messed up?
vigorous mixing solvents that will react with the solute solvents with high boiling point
57
what happens during vacuum filtration
air is sucked out of the bottom flask to increase filtration rate
58
what happens in recrystallization
impure product is dissolved into solvent, the solution is heated to melt the product, then is cooled and more pure solvent is solidified
59
what is an amine
any organic molecule with a basic nitrogen atom
60
what are the characteristics of amines? how do they act
they act as bases (function of thermodynamics) or nucleophiles (function of kinetics)
61
what is a formal charge
valance minus electrons surrounding atoms
62
how many valence electrons in C
4
63
how many valence electrons in N
5
64
how many valence electrons in O
6
65
how many valence electrons in F
7
66
alkane
/\/
67
alkene
/\\/
68
alkyne
\///
69
alcohol
OH /\/
70
ketone
...O || /\/\
71
ether
/\/O\/
72
what is the difference between R and S when it comes to stereochemistry
R is clockwise (the way you write it) S is counterclockwise
73
enantiomers
2 compounds with different absolute configuration at every stereocenter
74
absolute stereochemistry
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
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?
accept protons electron dense negatively charged strongest base forms the most stable product
76
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?
attacks electrophiles electron dense negatively charged strongest nucleophile attacks the fastest
77
what qualities does an electrophile have? charge? electron dense?
positively charged electron poor
78
compare and contrast E1/E2 steps speed carbocation formation product stereochem favored by
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
compare and contrast Sn1/Sn2 steps speed carbocation formation product stereochem favored by
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
what are radicals
they are dangerous and can cause DNA damage
81
are alkenes nucleo or electro philes? why?
nucleophiles electrons in a pi bond attack electrophile, leaving a carbocation (electrophile), which is then attacked by the nucleophile
82
the more substituents an alkene has, the (more/less) stable it is
more stable
83
alkynes have how many bonds?
triple
84
what defines an alcohol
-OH functional group
85
what is a benzene
hexagon, with the 3 lines inside it
86
boiling point (increases/decreases) with (increased/decreased) molecular weight and (increases/decreases) with more branching
boiling point increases with increased molecular weight and decreases with more branching
87
hydrogen bonding donors and acceptor
anything with an -OH or -NH can be a hydrogen bond donor anything with an -O,-N,-F is hydrogen bond acceptor
88
alcohols have (higher/lower) melting & boiling points and (higher/lower) stability due to the presence of hydrogen bonds
alcohols have higher melting & boiling points and higher stability
89
are alcohols more or less acidic than water
less acidic than water
90
what are some oxidizing agents
O3, Cr2O7, CrO4, KmnO4, Jones reagent, Collins reagent, PCC, PDC
91
what are the reducing agents (classify weak and strong)
weak: NaBH4 strong: LiAlH4, H2/Pressure
92
why are grignard synthesis important?
important because they allow us to add carbons to a chain
93
how does polarity and electronegativity go together?
larger the difference in electronegativity, the more polar a bond
94
which is more polar? C-O C-F
C-O is less polar C-F is more polar
95
what does a compound have to do to be considered an acid, in terms of a charge
either a partial or full positive charge
96
what does a compound have to do to be considered an base or nucleophile, in terms of a charge
either a partial or a full negative charge
97
how does charge relate to electronegativity
more electronegative: partial negative charge less electronegative: partial positive charge
98
how does charge relate to the withdrawing/donating of electrons?
full/partial positive: withdraw full/partial negative: donate
99
H donates or withdraws electrons? alkanes donates or withdraws electrons? alkenes donates or withdraws electrons?
H does neither alkanes donate alkenes withdraw
100
the (more/less) the conjugate base, the (stronger/weaker) the acid
the more stable the conjugate base, the stronger the acid
101
how does acidity and basicity relate to electron withdrawing/donating groups
withdrawing: increase compounds acidity donating: increase compounds basicity
102
do electron donating/withdrawing groups affect the stability of a compound?
yes
103
carbocations are more or less stable with more substituents?
more
104
are cyclic ethers highly reactive? if so why?
yes, due to their extreme ring strain
105
what is an ether
oxygen bonded to 2 are groups
106
The stereochemical designators α and β distinguish between
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
which is more chiral alpha or beta carbons
alpha
108
are carbonyl carbons achrial or chiral?
achiral
109
what do you do when asked to find out how many stereoisomers a "compound" has?
count the chiral centers = n 2^n
110
when finding discrete signals on a proton NMR spectrum, what do you do
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
which of these is the least reactive? ethanol diethyl ether dichloromethane acetone
diethyl ether
112
hydrophobic interaction chromatography relies one high or low salt concentrations
high salt concentrations

MCAT (13 decks)

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