Organic chemistry Flashcards
1
Q
Which chair form is the most stable
A
None H equatorial- equatorial are more stable than axial chair form
2
Q
When drawing your chairs and the question ask you to draw the more stable chair which chair formation is more stable
A
(Larger substituent) none H’s equatorial - equatorial position are more stable than axial chair position
3
Q
Which is stronger and which is weaker out of a pi(double bond) and sigma (single bond)
A
A single bond is stronger because it is more flexible and a double bond is weaker because it doesn’t have flexibility( Cannot rotate)
4
Q
What ionic formula would you see all nonmetal in the formula?
A
Ammonium
NH4OCH3
6
Q
When carbon is bonded with non-metal how is it charged?
A
Partial+
6
Q
What is a condensed formula?
A
Central atoms are shown with attach atoms essentially in sequence
C6H14
CH3CH2CH2CH2CH2CH3
Or
CH3(CH2)4CH3
7
Q
What cation lacks the octet rule?
A
H H C+(carbocation)
| |
H—O—C=C—C—H
+
Notice the C + only has 3 bonds
8
Q
When using the line (skeletal) formula,which atoms must be specified?
A
O - N
O - H
N - H
must be specified
9
Q
What is a condensed formula?
A
Central atoms are shown with attach atoms essentially in sequence
C6H14
CH3CH2CH2CH2CH2CH3
Or
CH3(CH2)4CH3
10
Q
What is a resonance structure?r
A
The ability to change a single Lewis structure that does not provide the adequate picture
Provides a larger amount of space for electrons to move around.
11
Q
How can you determine if a structure is resonance structure?
A
1) . Electrons move but atom do not move bonds/ lone pairs
2) . If an atom moves then you do not have resonance structure
12
Q
Allyllic resonance?
A
The most frequent resonance situation is when a charge atom is attached to a double bond it atom.
13
Q
Acid is a proton——————?
A
Donor
14
Q
Base is a proton —————?
A
Acceptor
15
Q
How does the conjugate relationship different?
A
The relationship differ by one hydrogen and one charge value -+
16
Q
Acid is a proton——————?
A
Donor
17
Q
Base is a proton —————?
A
Acceptor
18
Q
How does the conjugate relationship different?
A
The relationship differ by one hydrogen and one charge value -+
19
Q
Allyllic resonance?
A
The most frequent resonance situation is when a charge atom is attached to a double bond it atom.
20
Q
If an arrow➡️ starts with a lone pair points to an adjacent ATOM?
A
A new double bond is formed
.. ⤵️
A B+ ➡️A==B
The charges become neutral
21
Q
If a arrow starts at a single bond and is pointed to an atom?
A
The single bond breaks. if uncharged two new charges are formed
A—-B——> A+ ➕ B:-
22
Q
If an arrow starts with a bond and points towards an adjacent atom, the atom
A
The atom it’s pointed to will gain one additional lone pair and the single bond breaks
⤵️ ⤵️
A———B——-> A+. ➕. B-:
23
Q
If an arrow starts with a lone pair pointed to adjacent bond
A
The lone pair will turn into a bond to form single or double bond and be come neutral
24
Q
If an arrow starts with a lone pair and points towards an adjacent bond
A
A new double bond will form
⤵️. ⤵️
..
A. — B+ ➡️ A==B
..-
A=B+ ➡️ A⏭B
25
If an arrow points towards a bond…
The bond will increase
26
If an arrow starts from a double bond and point towards an adjacent atom
The double bond breaks and the single bond remain
..
A = B —-> A+———B-
27
If an arrow starts from a double bond and points to an adjacent bond
A new double bond is formed
⤵️ ⤵️
A= B - C —->> A+——B==C
28
If an arrow starts with a single bond and point towards a distant atom
The single bond brakes and a new single bond is formed
⤵️. ⤵️
A—-B C——-> A—- C B+
29
When at arrows starts at a double bond and point to a positively charged atom
The double bond breaks and become a single bond and a new single bond forms.
⤵️. ⤵️
x = Y + Z+ ——> X+——Y——Z
30
Can a you start arrow at a double bond to a C- carbon anion ( which has 1 lone pair)
If the
31
When you gain/ accept an electron you become more
Negative/anion
AcceptIng electrons
32
When you lose or donate an electron you become more
Positive/cation
33
An arrow must always point towards?
A atom bc when electrons move they always go to some new atom
34
If a bond is breaking the arrow should start from where?
The arrow to start from the bond that’s being broken
35
When bonds changes but formal charges doesn’t change
Substitution is involved
36
What is a substitution?
When an atom gives up an old bond and replace it with the new bond
37
Cation are more?
C+ N+O+
Acidic than neutral
38
Anions are more?
| C- N- O-
Basic
39
Conjugate acid (cation)
Ex: H3O
H2O
40
Conjugate base
| H2O
H3O
Weak acid
41
Conjugate acid (cation)
+NH4
42
Conjugate base
NH3
NH4
43
Neutral Acids Conjugate base are
Abnormal bonding and anion base
44
Which way does an equilibrium direction goes
Equilibrium goes towards the more stable or the normal bonding side
45
Acidic anion that gives resonance?
More acidic
46
Anion base that form resonance
Less basic
47
When using the line (skeletal) formula,which atoms must be specified?
O - N
O - H
N - H
must be specified
48
C/N/O/F
| ➡️
More acidic and stable
49
C/N/O/F
| ⬅️
More basic and less stable
50
Charged acids is more
Acidic than neutral acid
51
Stronger acid always makes
| H2O + NH2
A) (B
Stable conjugate weak Base
| -OH + NH3
B) (A
52
Stronger asset and stronger base are always on the same side
H2O + -NH2
(A) (B)
Weaker acid And weaker base are always on the same side
| -OH + NH3
B) (A
53
Carbanions are less stable than?
C+< N- < O- < F-
54
Equilibrium move towards?
Stable base
55
List the ways to determine if an atom structure is acidic/ stable?
1. Charged
2. Electronegativty
C-/N -/O-/F-
➡️➡️➡️➡️➡️➡️
3. Resonance is the tiebreaker
56
Anion base are more
Basic than a neutral base
57
4 electrons group has what type of shape and angle?
Tetrahedral shape
109° angle
sp3
58
3 electron groups has what type of shape and what is the angle?
Trigonal planar shape
120° angle
sp2
59
2 electron groups has what type of shape and angle?
linear shape
180° angle
sp
60
Hybridization: sp3
Tetrahedral/ 109° angle
61
Hybridization: sp2
Trigonal planar/ 120° angle
62
Hybridization:sp
Linear/180° angle
63
Remaining orbital ms for sp3?
Zero 0
64
Remaining orbital ms for sp2
One 1 orbital remains
65
Remaining orbital ms for sp?
2 remaining orbital
66
What are isomers? Or same
Different compounds with the same molecular formula
Same or single bonding
67
What are the different types of isomer
1. Structural isomer/constitutional isomer
2. Stereoisomers
68
What is structural isomer?
Isomers that differ in their bonding sequences that is, their atoms are connected differently
If the conditions formula or not the same then they are not structural isomers.
CH3CH2CH2CH3
Or
CH3
I
CH3—CH—CH3
69
What are Stereoisomers
It is an isomer that differ only in how their atoms are arranged in space. Their atoms are bonded in the same order.
H3C. CH3. H3C. H
\. /. \. /
C===C. Or C=====C
/. \. /. \
H. H. H. CH3
Cis (same). Tran(opposite)
Same condensed formula
70
sp2 will always have———— bonds
Double bond
72
How to determine basicity?
1. Look at the charge, is it negative charge
2. What is it electronegativity C/N/O/F
3. Resonance is the tiebreaker
4. Normal bindings or neutral is the most basic
73
How to determine if a molecule is non-polar
1. The central atom has no lone pairs
| 2. All attached atoms are the same
74
Which polarity bonds are the following?
C-C
C-H
C-halogen
Nonpolar
75
If weight is about equal which boiling point is higher?
1. H—bonding > Polar >Nonpolar
2. If H-bonding/ polarity comparable
Higher MW> Lower MW
3. dipole movement
76
When can hydrogen participate in hydrogen bonding?
When it is bonded to:
OH
NH
H-bonding
77
1s ➕1p =
sp/linear/180°
Remainder 2P unhybridized orbitals
78
1s ➕ 2p
sp2/trigonal planar/120°
Remain 1p unhybridized orbital
79
1s ➕3p =
sp3/ tetrahedral/109°
No remaining p
80
What is the first bond in any bond?
Sigma bond
81
Name the types of electron groups
1. Bonds: single,Double or triple it still counts as one electron group
2. Lone pair
82
What is the extra bond in a double or triple bond
Pi
83
What is London Force
The attractive force holding nonpolar together.
84
What is considered hydrogen bonding and what are their polarity.
Hydrogen bonding is consider if it is bonded to
OH
NH
H-F ( but it’s not a compound)
Strongly polarized.
85
What polarity are hydrocarbon
Nonpolar
86
What are the solubility rule
Like dissolve in like.
Good solubility
Polar solvents/polar solute
Nonpolar solvent/Nonpolar solute
Bad solubility
Polar solvent/Nonpolar solute
Nonpolar solvent/polar solute
87
HALOALKANE
C-C-C-C-Br (Cl,F)
Polarized partially-/+
Weak and breakable
C- F, C-Cl, C-Br, C-I bonds are present
88
ARENE
🛑-C-C-C🚓
Alternate double bonds in a six carbon ring
89
ALKYNE
C-C-C-C⏭C
Triple bond
Sp linear
DO NOT DRAW TRIPLE BOND zigzag on the center carbon
Hydrocarbon
Nonpolar
90
O
ll
-C-C-O-C
ESTER
Oxygen family
C=O (carbonyl)
O-C Directly attached
91
(CH3CH2)2NH
C-C-C-N-H-C-C
AMINE
Derivative of ammonia NH4
1 N
No C=O
Polar
Usually hydrogen is not drawn in the plane
Nitrogen lone pairs are basic/ dashes
Many drugs are amines
92
O
ll
C-C-C-C-NH2
AMIDES
C=O(carbonyl)
1 N, 1 C=O are directly attached
Polar
Proteins and emphasize consist of multiple amides
N lone pair is drawn with dashes
93
Functional group containing only carbon and hydrogen can only be what
Alkane
Alkene
Alkyne
94
Depending on what the carbonyl is attached to, compounds containing C=O are
Aldehyde
Ketone
Carboxylic acid
Ester
Anhydride
Amide
95
CARBOXYLIC
O
ll
C-C-C-C-OH
Oxygen family
C=O bonds with OH
Strong polarity and resonance stabilization of conjugated anions making these fairly acidic
96
KETONE
O
ll
C-C-C-C-C-C
Oxygen family
C=O (carbonyl) strongly polarized
2 C’s bonded to C=O
When drawing the structure note that Carbon chain on both sides ( more complex)
And when drawing to structure the lone pair is in plane
97
ALDEHYDE
O
Il
C-C-C-C-H
Oxygen family
C=O (carbonyl)strongly polarized
Carbon chain on one side
one H bond to C=O
Lone pair Are not attach when you’re drawing the structure
98
ESTER
C-C-C-O-C
Oxygen family
2 oxygen
C=O
O—C
99
ALCOHOL
C-C-C-C-C-OH
Oxygen
OH
Single bond
100
ALKENE
C-C-C-C=C
Double bond
Hydrocarbon
101
ALKANE
C-C-C-C-C
Hydrocarbon
Single bond
No heteroatoms
Anti- conformation/ best zigzag layout
102
How do you determine if and formula is polar
1. Lone pairs are present
| 2. O-H , N-H present H- binding
103
How to determine Boiling point
1. Is there a hydrogen bond
2. What is your polarity, non-polar or polar
3. Is London force in play; look at the molecular weight which is heavier
104
Methane
1-C
CH4
105
Methyl group
CH3–
106
Ethyl group
CH3-CH2-
107
Propyl group
CH3-CH2-CH2-
108
Butyl group
CH3-(CH2)2-CH2-
109
Ranking basicity?
1. Look at the charge, is it negative charge
2. What is it electronegativity C/N/O/F
3. Resonance is the tiebreaker
4. Normal bindings or neutral is the most basic
110
Pentyl group
CH3-(CH2)3-CH2
111
Iso/propyl or isobutyl group
CH3-CH-CH3 (propyl)
CH3-CH-CH3-CH2 (butyl)
112
Isopropyl
CH3-CH-CH3
113
t-butyl or tert-butyl
```
CH3
l
CH3–C—
l
CH3
Looks like a T shape formula
114
Ethane
C2H6
H-(CH2)2-H
Boiling point:--89°C
115
Propane
C3H8
H-(CH2)3-H
BP: -42°C
116
Butane
C4H10
H-(CH2)4-H
Boiling point is 0°C Room Temperature
117
Pentane
C5H12
H-(CH2)4-H
Boiling .36°C
118
HEXANE
C6H14
H-(CH2)6-H
Bowling .69°C
119
Staggered
The hydrogen atom on the back carbon staggered halfway between the hydrogen on the front carbon.
When bonds are far apart as possible: 60°, 180°, 300°
The normal zigzag structure
Staggered bonds are the most stable
120
Eclipsed
Hydrogen atoms on the back carbon are hidden by those on the front carbon
When bonds are aligned. 0°, 120°, 240°, 360° dihedral angles
Eclipse bonds are the most unsolved
121
What is the Newman Project
Looking straight down on confirmation carbon bonds
C-C
122
Dihedral angle
Angle between a bond on the front atom relative to a bond on the back atom
123
What is torsional strain?
The resistant to rotate and potential energy increase
Inability to achieve stagger confirmation
For the torsional strain is repulsion between BONDS & ELECTRONS pairs
From the ECLIPSE BONDS only!
124
What is steric strain
When atoms get too close. Atoms to atom repulsion
Are any items to close
Stir it gets worse as things gets bigger and closer together
125
What is angle strain
Bonds angles cannot achieve VSEPR ideal angles. 🔼🟰
They are anybody angles for us to be together then ideal
NEVER HAPPEN IN ACYCLIC
126
Why are staggered better than eclipse?
Cause in staggered confirmation the atom groups are between 60°, 180°or 300° apart
Eclipse are aligned. 0°, 120°, 240°, 360°
127
Why is Eclips better than total eclipse?
Total eclipse is when the two methyl groups are pointing in the same direction
CH3. CH3 0° angle apart making steric worst
Eclipse is when the methyl groups are at least 120° apart making it less steric strain
128
Why is anti-better than Gauche?
Because anti is when the largest substituents are as far as possible from one another 180°. The most stable.
Most space possible between the largest group.
Gauche Would still have steric straight even though there was nobody eclipsing zero torsion strain
129
Why is gauche better than eclipse?
Because in gauche,although the largest substituents/groups are adjacent to one another 60° apart and eclipse are 120° angles apart. The eclipse requires more energy.
Gauche energy is only slightly higher engery than anti
130
Rank anti, gauche, eclipse and total eclipse
1. Anti< gauche < eclipse < totally eclipse
131
Heptane
C7H16
H-(CH2)7-H
Bowling point is 98°C
132
Nonane
C9H20
H-(CH2)9-H
151°C
133
Octane
C8H18
H-(CH2)8-H
Boiling point: 126°C
134
Decane
C10H22
H-(CH2)10-H
Boiling point .174°C
135
What is Newman project?
How are they drawn?
Newman project is a way of looking straight down the bottom connecting to carbons
1. Draw a circle (back carbon) with the dot in the middle
2. To add three sticks extending from the peripheral of the circle with one of them straight up
3. Extending from the center Dot (front carbon) to illustrate the bond radiating from the front carbon.
l
-🔘-
/ l \
136
What is an anti conformed
A confirmation in which the largest Substituent are far apart as possible 180°
137
Skew
Anything else in between the eclipse and a staggered extremes
138
Steps to naming alkanes
1. Find longest chain
2. How many substituent are attached to the carbon chain
3. Number the location (Count from the direction of the nearest substitute)
4. If more than two substituents are present use the prefix di-(2), tri-(3), and tetra-4
139
Rotation barrier is dictated by how bad what
It is dictated by how bad the total eclipse is the torsion same for all but steric gets worse as they get bigger
140
If you are in the zigzag formation what are you more likely to be into confirmation or gauche?
Anti- conformation
If you add a wedge 🔼or a dash 📶 then it becomes a gauche
141
When identifying same, structural or stereoisomer can single bond isomers rotate
Isomers that are single bond and can rotate are the same
142
When identifying same, structural or stereoisomer can single bond isomers rotate
Isomers that are single bond and can rotate are the same
143
Cyclohexane
There is no angle strain or torsion strain
109° tetrahedral angle, Staggered
No eclipse sing carbon Bon
144
Cyclohexane
There is no angle strain or torsion strain
109° tetrahedral angle, Staggered
No eclipse sing carbon Bon
145
How to determine which chair is more stable
1. Is it equatorial
| 2. Is it bigger ( bigger sterically whole avoid axial
146
When determining axial and equatorial stability, if both substituents are axial which is better?
Bigger axial it’s worse because they’re more unstable
147
How to determine if a structural is an Acyclic or an Cyclic structure
Acyclic: Look at H 👀: (# of C x 2) ➕ H2️⃣
Cyclic: ratio of H : C is 1:2
148
How to determine which chair is more stable
1. Is it equatorial
| 2. Is it bigger ( bigger sterically whole avoid axial
149
When determining axial and equatorial stability, if both substituents are axial which is better?
Bigger axial it’s worse because they’re more unstable
150
How to determine if a structural is an Acyclic or an Cyclic structure
Acyclic: Look at H 👀: (# of C x 2) ➕ H2️⃣
Cyclic: ratio of H : C is 1:2
151
Hydrocarbon primary polarity
NONPOLAR
152
When drawing a newton structure two wage bought indicate that both systems to WinStar on
Same face playing of the ring
153
How to determine solubility
1. If you have N’s , O’s in molecular are soluble in water
| 2. More C’s the less soluble ( carbon makes you more nonpolar )
154
Alkanes branches Formula
The formula is the same for a Acyclic alkane.
Multiply carbon times two and add two more
155
How do you name the alkanes
1. First find the longest chain ( last part of name)
2. Name it the longest substituent attach. ( methyl, ethyl, isobut)
3. If more than one substituent Give it the number of the carbon it is attached to. (start counting from the direction where the closest substituent is located)
Remember to put a-between the numbers or commas if there is consecutive numbers.
4. If more than two substituents are present
Add “di”, tri, “tetra”
156
What would be the rotation barrier
Rotation barrier is dictated by how bad total eclipse is. Torsional same for all. But stir it gets worse the bigger they are
1. CH3——C——CH3
2. CH——CH2——CH2—CH3
157
Naming cycloalkanes?
1. Follow the same steps as the alkanes
2. Determine if it’s cis or trans (disubstituted)
3. Number the rings
158
What is the most stable ring size
6
| 0 rings strain
159
How do you draw Cis & Tran disubstituted cyclohexane
1. Draw right and left chair
2. Make sure the (L) most carbon is the same on both structure
3. Draw the axial structure (up/down)
4. Draw the equatorial horizontal line)
5. Put the substituent on the left most carbon first and make sure if you put it on the axle on the right chair it must go on the equatorial on the left chair
6. Use the 🆙📈logic to decide whether the second substituent belong on the axial or equatorial
7. If it’s Cis both statuettes are 🆙 🆙or both substituents are down⬇️⬇️
160
If the 2 substitute are eq/ eq or ax/ ax, What is it stability
Equatorial is better than axial for steric
Eq/ Eq is better
Ax/ Ax worst
161
Alkanes branches Formula
The formula is the same for a Acyclic alkane.
Multiply carbon times two and add two more
162
How do you name the alkanes
1. First find the longest chain ( last part of name)
2. Name it the longest substituent attach. ( methyl, ethyl, isobut)
3. If more than one substituent Give it the number of the carbon it is attached to. (start counting from the direction where the closest substituent is located)
Remember to put a-between the numbers or commas if there is consecutive numbers.
4. If more than two substituents are present
Add “di”, tri, “tetra”
163
If the 2 substitute are eq/ eq or ax/ ax, What is it stability
Equatorial is better than axial for steric
Eq/ Eq is better
Ax/ Ax worst
164
How do you draw Cis & Tran cyclohexane
1. Draw right and left chair
2. Make sure the (L) most carbon is the same on both structure
3. Draw the axial structure (up/down)
4. Draw the equatorial horizontal line)
5. Put the substituent on the left most carbon first and make sure if you put it on the axle on the right chair it must go on the equatorial on the left chair. Put the H’s next to each substituents
6. Use the 🆙📈logic to decide where the second substituent goes.
7. If it as for the cis/tran: Cis both substituents are 🆙 🆙or both substituents are down⬇️⬇️
8. However, if it’s a cis/tran question and there both eq- ax, select the chair with the smaller substituent on the axial.
165
What is the most stable ring size
6
| 0 rings strain
166
Naming cycloalkanes?
1. Follow the same steps as the alkanes
2. Determine if it’s cis or trans (disubstituted)
3. Number the rings
167
What would be the rotation barrier
Rotation barrier is dictated by how bad total eclipse is. Torsional same for all. But steric it gets worse the bigger they are
1. CH3——C——CH3
2. CH——CH2——CH2—CH3
168
When drawing a newmanstructure two wage bought indicate that both systems to WinStar on
Same face playing of the ring
168
Cis/Tran isomer (geometric isomer):
They are Stereoisomers
differ in their cis/ tran arrangement on double bond or on rings
169
How to determine basicity?
1. Look at the charge, is it negative charge
2. What is it electronegativity C/N/O/F
3. Resonance is the tiebreaker
4. Normal bindings or neutral is the most basic
170
Which functional group contains both? Carbonyl =O and hydroxy O-H?
Carboxylic acid
C
II
C-C-C-C-OH
171
Which functional group contain hydroxyl ?
Alcohol
Carboxylic acid
172
What functional group contains Carbonyl?
C=O
Aldehydes,
O
II
C-C-H
Ketones
O
II
C-C-C
Ester
O
II
C-C-C-NH
