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Anesthesia Interview Review > Organic chemistry > Flashcards

Organic chemistry Flashcards

1
Q

Which chair form is the most stable

A

None H equatorial- equatorial are more stable than axial chair form

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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

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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)

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4
Q

What ionic formula would you see all nonmetal in the formula?

A

Ammonium

NH4OCH3

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6
Q

When carbon is bonded with non-metal how is it charged?

A

Partial+

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6
Q

What is a condensed formula?

A

Central atoms are shown with attach atoms essentially in sequence

     C6H14

CH3CH2CH2CH2CH2CH3

    Or

CH3(CH2)4CH3

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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

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8
Q

When using the line (skeletal) formula,which atoms must be specified?

A

O - N

O - H

N - H

must be specified

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9
Q

What is a condensed formula?

A

Central atoms are shown with attach atoms essentially in sequence

     C6H14

CH3CH2CH2CH2CH2CH3

    Or

CH3(CH2)4CH3

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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.

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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

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12
Q

Allyllic resonance?

A

The most frequent resonance situation is when a charge atom is attached to a double bond it atom.

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13
Q

Acid is a proton——————?

A

Donor

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14
Q

Base is a proton —————?

A

Acceptor

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15
Q

How does the conjugate relationship different?

A

The relationship differ by one hydrogen and one charge value -+

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16
Q

Acid is a proton——————?

A

Donor

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17
Q

Base is a proton —————?

A

Acceptor

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18
Q

How does the conjugate relationship different?

A

The relationship differ by one hydrogen and one charge value -+

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19
Q

Allyllic resonance?

A

The most frequent resonance situation is when a charge atom is attached to a double bond it atom.

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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

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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:-

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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-:

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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

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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

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25
Q

If an arrow points towards a bond…

A

The bond will increase

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26
Q

If an arrow starts from a double bond and point towards an adjacent atom

A

The double bond breaks and the single bond remain
..
A = B —-> A+———B-

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27
Q

If an arrow starts from a double bond and points to an adjacent bond

A

A new double bond is formed
⤵️ ⤵️
A= B - C —-» A+——B==C

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28
Q

If an arrow starts with a single bond and point towards a distant atom

A

The single bond brakes and a new single bond is formed

⤵️. ⤵️
A—-B C——-> A—- C B+

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29
Q

When at arrows starts at a double bond and point to a positively charged atom

A

The double bond breaks and become a single bond and a new single bond forms.
⤵️. ⤵️
x = Y + Z+ ——> X+——Y——Z

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30
Q

Can a you start arrow at a double bond to a C- carbon anion ( which has 1 lone pair)

A

If the

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31
Q

When you gain/ accept an electron you become more

A

Negative/anion

AcceptIng electrons

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32
Q

When you lose or donate an electron you become more

A

Positive/cation

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33
Q

An arrow must always point towards?

A

A atom bc when electrons move they always go to some new atom

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34
Q

If a bond is breaking the arrow should start from where?

A

The arrow to start from the bond that’s being broken

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35
Q

When bonds changes but formal charges doesn’t change

A

Substitution is involved

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36
Q

What is a substitution?

A

When an atom gives up an old bond and replace it with the new bond

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37
Q

Cation are more?

C+ N+O+

A

Acidic than neutral

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38
Q

Anions are more?

C- N- O-

A

Basic

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39
Q

Conjugate acid (cation)

Ex: H3O

A

H2O

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40
Q

Conjugate base

H2O

A

H3O

Weak acid

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41
Q

Conjugate acid (cation)

A

+NH4

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42
Q

Conjugate base

NH3

A

NH4

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43
Q

Neutral Acids Conjugate base are

A

Abnormal bonding and anion base

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44
Q

Which way does an equilibrium direction goes

A

Equilibrium goes towards the more stable or the normal bonding side

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45
Q

Acidic anion that gives resonance?

A

More acidic

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46
Q

Anion base that form resonance

A

Less basic

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47
Q

When using the line (skeletal) formula,which atoms must be specified?

A

O - N

O - H

N - H

must be specified

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48
Q

C/N/O/F

➡️

A

More acidic and stable

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49
Q

C/N/O/F

⬅️

A

More basic and less stable

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50
Q

Charged acids is more

A

Acidic than neutral acid

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51
Q

Stronger acid always makes

H2O + NH2
A) (B

A

Stable conjugate weak Base

-OH + NH3
B) (A

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52
Q

Stronger asset and stronger base are always on the same side
H2O + -NH2
(A) (B)

A

Weaker acid And weaker base are always on the same side

-OH + NH3
B) (A

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53
Q

Carbanions are less stable than?

A

C+< N- < O- < F-

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54
Q

Equilibrium move towards?

A

Stable base

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55
Q

List the ways to determine if an atom structure is acidic/ stable?

A
  1. Charged
  2. Electronegativty
    C-/N -/O-/F-
    ➡️➡️➡️➡️➡️➡️
  3. Resonance is the tiebreaker
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56
Q

Anion base are more

A

Basic than a neutral base

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57
Q

4 electrons group has what type of shape and angle?

A

Tetrahedral shape

109° angle

sp3

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58
Q

3 electron groups has what type of shape and what is the angle?

A

Trigonal planar shape

120° angle

sp2

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59
Q

2 electron groups has what type of shape and angle?

A

linear shape

180° angle

sp

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60
Q

Hybridization: sp3

A

Tetrahedral/ 109° angle

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61
Q

Hybridization: sp2

A

Trigonal planar/ 120° angle

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62
Q

Hybridization:sp

A

Linear/180° angle

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63
Q

Remaining orbital ms for sp3?

A

Zero 0

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64
Q

Remaining orbital ms for sp2

A

One 1 orbital remains

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65
Q

Remaining orbital ms for sp?

A

2 remaining orbital

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66
Q

What are isomers? Or same

A

Different compounds with the same molecular formula

Same or single bonding

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67
Q

What are the different types of isomer

A
  1. Structural isomer/constitutional isomer
  2. Stereoisomers
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68
Q

What is structural isomer?

A

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
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69
Q

What are Stereoisomers

A

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
Q

sp2 will always have———— bonds

A

Double bond

72
Q

How to determine basicity?

A
  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
Q

How to determine if a molecule is non-polar

A
  1. The central atom has no lone pairs

2. All attached atoms are the same

74
Q

Which polarity bonds are the following?
C-C

C-H

C-halogen

A

Nonpolar

75
Q

If weight is about equal which boiling point is higher?

A
  1. H—bonding > Polar >Nonpolar
  2. If H-bonding/ polarity comparable
    Higher MW> Lower MW
  3. dipole movement
76
Q

When can hydrogen participate in hydrogen bonding?

A

When it is bonded to:

OH

NH

H-bonding

77
Q

1s ➕1p =

A

sp/linear/180°

Remainder 2P unhybridized orbitals

78
Q

1s ➕ 2p

A

sp2/trigonal planar/120°

Remain 1p unhybridized orbital

79
Q

1s ➕3p =

A

sp3/ tetrahedral/109°

No remaining p

80
Q

What is the first bond in any bond?

A

Sigma bond

81
Q

Name the types of electron groups

A
  1. Bonds: single,Double or triple it still counts as one electron group
  2. Lone pair
82
Q

What is the extra bond in a double or triple bond

A

Pi

83
Q

What is London Force

A

The attractive force holding nonpolar together.

84
Q

What is considered hydrogen bonding and what are their polarity.

A

Hydrogen bonding is consider if it is bonded to

OH

NH

H-F ( but it’s not a compound)

Strongly polarized.

85
Q

What polarity are hydrocarbon

A

Nonpolar

86
Q

What are the solubility rule

A

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
Q

HALOALKANE

         C-C-C-C-Br (Cl,F)
A

Polarized partially-/+
Weak and breakable
C- F, C-Cl, C-Br, C-I bonds are present

88
Q

ARENE

                           🛑-C-C-C🚓
A

Alternate double bonds in a six carbon ring

89
Q

ALKYNE

                       C-C-C-C⏭C
A

Triple bond

Sp linear

DO NOT DRAW TRIPLE BOND zigzag on the center carbon

Hydrocarbon

Nonpolar

90
Q

O
ll
-C-C-O-C

A

ESTER

Oxygen family

C=O (carbonyl)

O-C Directly attached

91
Q

(CH3CH2)2NH

C-C-C-N-H-C-C

A

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
Q

O
ll
C-C-C-C-NH2

A

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
Q

Functional group containing only carbon and hydrogen can only be what

A

Alkane

Alkene

Alkyne

94
Q

Depending on what the carbonyl is attached to, compounds containing C=O are

A

Aldehyde

Ketone

Carboxylic acid

Ester

Anhydride

Amide

95
Q

CARBOXYLIC

          O
          ll C-C-C-C-OH
A

Oxygen family

C=O bonds with OH

Strong polarity and resonance stabilization of conjugated anions making these fairly acidic

96
Q

KETONE

    O 
     ll  C-C-C-C-C-C
A

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
Q

ALDEHYDE

         O 
         Il  C-C-C-C-H
A

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
Q

ESTER

C-C-C-O-C

A

Oxygen family

2 oxygen

C=O

O—C

99
Q

ALCOHOL

C-C-C-C-C-OH

A

Oxygen
OH
Single bond

100
Q

ALKENE

                          C-C-C-C=C
A

Double bond

Hydrocarbon

101
Q

ALKANE

                    C-C-C-C-C
A

Hydrocarbon

Single bond

No heteroatoms

Anti- conformation/ best zigzag layout

102
Q

How do you determine if and formula is polar

A
  1. Lone pairs are present

2. O-H , N-H present H- binding

103
Q

How to determine Boiling point

A
  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
Q

Methane

A

1-C

CH4

105
Q

Methyl group

A

CH3–

106
Q

Ethyl group

A

CH3-CH2-

107
Q

Propyl group

A

CH3-CH2-CH2-

108
Q

Butyl group

A

CH3-(CH2)2-CH2-

109
Q

Ranking basicity?

A
  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
Q

Pentyl group

A

CH3-(CH2)3-CH2

111
Q

Iso/propyl or isobutyl group

A

CH3-CH-CH3 (propyl)

CH3-CH-CH3-CH2 (butyl)

112
Q

Isopropyl

A

CH3-CH-CH3

113
Q

t-butyl or tert-butyl

A

~~~
CH3
l
CH3–C—
l
CH3

Looks like a T shape formula

114
Q

Ethane

A

C2H6

H-(CH2)2-H

Boiling point:–89°C

115
Q

Propane

A

C3H8

H-(CH2)3-H

BP: -42°C

116
Q

Butane

A

C4H10

H-(CH2)4-H

Boiling point is 0°C Room Temperature

117
Q

Pentane

A

C5H12

H-(CH2)4-H

Boiling .36°C

118
Q

HEXANE

A

C6H14

H-(CH2)6-H

Bowling .69°C

119
Q

Staggered

A

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
Q

Eclipsed

A

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
Q

What is the Newman Project

A

Looking straight down on confirmation carbon bonds

C-C

122
Q

Dihedral angle

A

Angle between a bond on the front atom relative to a bond on the back atom

123
Q

What is torsional strain?

A

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
Q

What is steric strain

A

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
Q

What is angle strain

A

Bonds angles cannot achieve VSEPR ideal angles. 🔼🟰

They are anybody angles for us to be together then ideal

NEVER HAPPEN IN ACYCLIC

126
Q

Why are staggered better than eclipse?

A

Cause in staggered confirmation the atom groups are between 60°, 180°or 300° apart

Eclipse are aligned. 0°, 120°, 240°, 360°

127
Q

Why is Eclips better than total eclipse?

A

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
Q

Why is anti-better than Gauche?

A

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
Q

Why is gauche better than eclipse?

A

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
Q

Rank anti, gauche, eclipse and total eclipse

A
  1. Anti< gauche < eclipse < totally eclipse
131
Q

Heptane

A

C7H16

H-(CH2)7-H

Bowling point is 98°C

132
Q

Nonane

A

C9H20

H-(CH2)9-H

151°C

133
Q

Octane

A

C8H18

H-(CH2)8-H

Boiling point: 126°C

134
Q

Decane

A

C10H22

H-(CH2)10-H

Boiling point .174°C

135
Q

What is Newman project?

How are they drawn?

A

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
Q

What is an anti conformed

A

A confirmation in which the largest Substituent are far apart as possible 180°

137
Q

Skew

A

Anything else in between the eclipse and a staggered extremes

138
Q

Steps to naming alkanes

A
  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
Q

Rotation barrier is dictated by how bad what

A

It is dictated by how bad the total eclipse is the torsion same for all but steric gets worse as they get bigger

140
Q

If you are in the zigzag formation what are you more likely to be into confirmation or gauche?

A

Anti- conformation

If you add a wedge 🔼or a dash 📶 then it becomes a gauche

141
Q

When identifying same, structural or stereoisomer can single bond isomers rotate

A

Isomers that are single bond and can rotate are the same

142
Q

When identifying same, structural or stereoisomer can single bond isomers rotate

A

Isomers that are single bond and can rotate are the same

143
Q

Cyclohexane

A

There is no angle strain or torsion strain

109° tetrahedral angle, Staggered
No eclipse sing carbon Bon

144
Q

Cyclohexane

A

There is no angle strain or torsion strain

109° tetrahedral angle, Staggered
No eclipse sing carbon Bon

145
Q

How to determine which chair is more stable

A
  1. Is it equatorial

2. Is it bigger ( bigger sterically whole avoid axial

146
Q

When determining axial and equatorial stability, if both substituents are axial which is better?

A

Bigger axial it’s worse because they’re more unstable

147
Q

How to determine if a structural is an Acyclic or an Cyclic structure

A

Acyclic: Look at H 👀: (# of C x 2) ➕ H2️⃣

Cyclic: ratio of H : C is 1:2

148
Q

How to determine which chair is more stable

A
  1. Is it equatorial

2. Is it bigger ( bigger sterically whole avoid axial

149
Q

When determining axial and equatorial stability, if both substituents are axial which is better?

A

Bigger axial it’s worse because they’re more unstable

150
Q

How to determine if a structural is an Acyclic or an Cyclic structure

A

Acyclic: Look at H 👀: (# of C x 2) ➕ H2️⃣

Cyclic: ratio of H : C is 1:2

151
Q

Hydrocarbon primary polarity

A

NONPOLAR

152
Q

When drawing a newton structure two wage bought indicate that both systems to WinStar on

A

Same face playing of the ring

153
Q

How to determine solubility

A
  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
Q

Alkanes branches Formula

A

The formula is the same for a Acyclic alkane.

Multiply carbon times two and add two more

155
Q

How do you name the alkanes

A
  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
Q

What would be the rotation barrier

A

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
Q

Naming cycloalkanes?

A
  1. Follow the same steps as the alkanes
  2. Determine if it’s cis or trans (disubstituted)
  3. Number the rings
158
Q

What is the most stable ring size

A

6

0 rings strain

159
Q

How do you draw Cis & Tran disubstituted cyclohexane

A
  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
Q

If the 2 substitute are eq/ eq or ax/ ax, What is it stability

A

Equatorial is better than axial for steric

Eq/ Eq is better

Ax/ Ax worst

161
Q

Alkanes branches Formula

A

The formula is the same for a Acyclic alkane.

Multiply carbon times two and add two more

162
Q

How do you name the alkanes

A
  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
Q

If the 2 substitute are eq/ eq or ax/ ax, What is it stability

A

Equatorial is better than axial for steric

Eq/ Eq is better

Ax/ Ax worst

164
Q

How do you draw Cis & Tran cyclohexane

A
  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
Q

What is the most stable ring size

A

6

0 rings strain

166
Q

Naming cycloalkanes?

A
  1. Follow the same steps as the alkanes
  2. Determine if it’s cis or trans (disubstituted)
  3. Number the rings
167
Q

What would be the rotation barrier

A

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
Q

When drawing a newmanstructure two wage bought indicate that both systems to WinStar on

A

Same face playing of the ring

168
Q

Cis/Tran isomer (geometric isomer):

A

They are Stereoisomers

differ in their cis/ tran arrangement on double bond or on rings

169
Q

How to determine basicity?

A
  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
Q

Which functional group contains both? Carbonyl =O and hydroxy O-H?

A

Carboxylic acid
C
II
C-C-C-C-OH

171
Q

Which functional group contain hydroxyl ?

A

Alcohol

Carboxylic acid

172
Q

What functional group contains Carbonyl?

C=O

A

Aldehydes,
O
II
C-C-H

Ketones
O
II
C-C-C

Ester
O
II
C-C-C-NH

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