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Anesthesia Interview Review > Organic Chem Test 2 > Flashcards

Organic Chem Test 2 Flashcards

1
Q

What is the mechanism of radical chain reaction

A

Mechanism is a complete step-by-step description of exactly which bond breaks and bonds form in which giving a product.

CH3 + Cl———-> CH3Cl + HCl + CH3 + CCl4

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2
Q

What’s is a reactive intermediate and give an example of the process

A

A short lived species that never present high concentration bc it reacts quickly.

Example: Chlorine, it is a halogen

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3
Q

What are the three factors in every reaction

A
  1. Mechanism: Step by step description of how bonds break and which bonds are made/ formed
  2. Thermodynamics: study of the energy changes that accompany chemical and physical reaction
  3. Kinetics: study of reaction rates, determining which product are formed fastest.
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4
Q

What are the phases of mechanism

A
  1. Initiation: generates a reactive intermediate
    ( occur when non radical produces one or more radical)
  2. Propagation: step in which the reactive intermediate reacts with stable molecular to form a product and another reactive intermediate(free radical). The chain continues till supply is gone. ( occur when a radical reacts with a non radical to yield a different radical and a different non radical)
  3. Termination: slow or stop the reactions
    (occurs when two radical react to form a nonradical)
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5
Q

What is a radical

A

a unpaired electron

A radical never satisfy the octet rule

A radical is highly unstable and highly reactive

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6
Q

Whatever are the steps of propagation?

A

Steps:

  1. The radical removes an election from a stable molecule, thus forming a bond
    This reaction product 2 new product.
    One is the final product and the other is a free radical
  2. Regeneration of radicals…continuing to the chain
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7
Q

How does termination occur?

A

Two free radical combines thus stopping free radical formation

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8
Q

Halogen radical stability ranking

A

H—F ➡️ H•. Least Stable/reactive F•

H—Cl ➡️ H•. Cl•

H—Br ➡️ H•. Br•

H—I ➡️ H•. Most stable I•

Less stable = faster reactant

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9
Q

What is carbons bond strength pattern

A

CH3—F. Strongest
109

CH3–Cl. 🆙⬆️
84

CH3–Br. 🆙⬆️
70

CH3–I. 🆙⬆️Weakest/breakable

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10
Q

Why are H—F, and Cl—F stronger than

H—I and C—I bonds?

A
  1. Because of electronegativity and radical stability
    • Radicals does not follow the optic
    rules so electrons are poor
    • because F is more electronegative it is least
    willing to be electron poor
    • electronegativity decreases as you move down
    the table therefore it is less problems to
    become a radical
  2. The atomic size and orbital overlap
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11
Q

Heterolysis

A

When you break to electron bonds both electrons go the same direction and one of the atom is going to keep both of them

Ions are involved/NO RADICAL

Double barbed arrow

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12
Q

Homolysis

A

To electron bonds are gonna break in half. One electron goes one direction and the other electron goes in a different direction.

Single barbed arrow

This always involve radicals

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13
Q

Free Energy (🔺G)

A

A reaction that is negative, which is a favorable reaction
Corresponding to a decrease in energy

Exothermic: if weaker bond are broken and strong bonds are formed yield a (negative value of 🔺H)

Endothermic: if stronger bonds are broken and weaker bond are formed, energized consumed in the reaction (positive + value of 🔺G)

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14
Q

How can you use bond energies to calculate energy changes

A
  1. Compare the energies of both bonds versus the bond made

Free energy(🔺G) = Enthalpy( heat of reaction 🔺T) - Entropy(freedom of movement T🔺S)

Cl•. H—CH3➡️ ➡️CH3• + H-Cl
104. 103. =🔺H= + 1

Cl——Cl. CH3 ➡️➡️➡️ Cl• +. Cl—CH3
58. 84. 🔺H= -26

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15
Q

What is kinetic?

A

The study of reaction rate

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16
Q

Activation energy

A

The minimum kinetic energy the moles must have to overcome the repulsion between their electrons cloud when they collide.
(Difference between the energy of the starting material and the energy of the transition state)

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17
Q

Know the difference between primary secondary and tertiary, which carbon- hydrogen is like used to bond.

A

The reason tertiary bonds are more acceptable is because energy required to remove hydrogen is lower. It’s more stable and can react quicker to form a free radical by breaking bonds between a hydrogen atom carbon. this energy is greatest for a methyl CH3 carbon and it is decreased for a primary carbon(CH3) and a secondary carbon(CH2) and a tertiary(CH) carbon the more highly substitute the carbon the less energy is required to form the free radical.

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18
Q

Which steps determines rate

A

Propagation 1 step. In this step radicals and non-radicals are breaking and forming bond. Hydrogen select to bond is based on 1°, 2°, 3°. The energy required to break bonds and form bonds is lower in 3°, the secondary radical is form faster

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19
Q

Which energy determines rate

A

Endothermic unfavorable)slower: In the endothermic reaction the transition is closer to the product and energy and in structure

Exothermic (favorable) faster and stable: In an exothermic reaction the transition state is closer to the reactant in energy and in structure

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20
Q

The order of relative stability of radicals is

A 
Allylic
3° 2° 1°
Methy 
Alkenyl(vinyl)
F>Cl>Br>I
21
Q

Order of stability for carboncations

A

Allylic
3° 2° 1°
Methyl
Alkenyl(vinyl)

22
Q

Order of stability for carbanions

A 
Allylic
Alkenyl (vinyl)
Methyl
1° 2° 3°
C/N/O/F (increase L->R)
(Bottom->Top)
23
Q

The more stable than reactive

A

The less reactive or slower rate

24
Q

What is basic stability

A

The more basic a structure is the least stable but the more stable the structure is the least basic

25
Q

Electrophilicity Reactivity

SN1,SN2,E2

A

I>Br>Cl

26
Q

Product stability/Reactivity Principle 

A

The more stable the product the faster the reaction

27
Q

Transition state stability/reactivity possible

A

The more stable to reactant the slower it reacts

28
Q

Br is more stable than Cl

A

Br• is more selective and choosy to make better to degree radical rather than the less Stable 1° radical

Cl• is less stable and ready to react quickly doesn’t want to wait for a 2° hydrogen it often settles for a stronger 1° hydrogen even though it gives an inferior 1° radical

29
Q

Acid stability

A 
Cation
Halogen 
Anion allylic 
Neutral allylic 
Electronegative 
C/N/O/F
30
Q

Chiral carbon

A

Tetrahedral atom with 4 attached group

31
Q

Achiral

A

0 chiral carbon = achiral
Mirror image
Plane of symmetry with 2 chiral center
Also called meso (optically inactive)

32
Q

Chiral

A

1 chiral carbon= chiral
Looks like mirror image but different just like a left hand is different from the right hand.
Reaction slower therefore it is more stable

33
Q

How to draw mirrors/enantiomers

A

Flip everything. If in front flip to back n Vice versa

34
Q

How to determine if a structure is same

A

If 1 carbon center assign R/R = same 

2 carbon center everything flip = same

35
Q

How to determine if it is an enantiomer

A

Flip everything and if it has the mirror image it is an enantiomer

36
Q

Enantiomer has everything the same except

A
  1. Reactivity

2. Optic activity

37
Q

Name chiral carbon using R & S

A

Ex (R) -2-bromobutane

38
Q

When is a solution racemic versus optically active

A

Racemic: 50/50 mixture of 2 enantiomer(optically inactive), does not rotate light, chiral

Optically active: rotates polarize light, equal but opposite directions
Optically active indicate the presence of a chiral molecule

39
Q

Disastereomers

A

Cis/Tran stereoisomers NOT enantiomer

They have different melting points, boiling point, solubility unlike enantiomer

40
Q

What is the rule for the number of potential stereoisomer

A

2^2

41
Q

How to draw all unique Stereoisomers

A
  1. First draw the skeleton
  2. If it is an even number of carbon draw the eclipse symmetrical form, if it is an odd number draw the zigzag carbon form
  3. Add attachments
  4. Draw the cis/trans form
  5.  determine if chiral or achiral
  6. If it is a chai roll then draw the mirror version of it (exchange all the attachment hash and wedge)
  7. If it is diastereomer (cis/Tran)
42
Q

Enantiomer

A

Stereoisomers that are not superimposed on their mirrors reflection.
Optically active
If you flip the front and back or left and right and the new image looks the different than the original it an enantiomer

43
Q

SN2 substitution

A 
REACTIVE STABILITY:
Allylic 1° >2° >3° >vinyl
I>BR>CL>F
C>N>O>F
RECOGNITION:
Anion nucleophiles

RANKING:
1° or 2° alkyl halide

Predict: Replace halide with the anion nucleophile

STEREOCHEMISTRY:
Inversion when a 2° R—X is involved 

44
Q

E2

A

REACTIVE STABILITY:
3°> 2° > 1°.> vinyl
I>Br>Cl

RECOGNITION:
A. Anionic nucleophile
B. 3°, 2° alkyl halide

STEREOCHEMISTRY:
Cis/Tran elimination (must have)

PREDICTING PRODUCT:
Remove halide and a HYDROGEN from neighboring carbon. Hydrogen must me Tran 

MECH: 1 step

45
Q

SN1

A

REACTIVE STABILITY:
3° >2° > 1°>vinyl
I>Br>Cl

RECOGNITION:
A. Neutral nucleophile

B. 3°, 2°

PREDICTING PRODUCT:
Removing halide and replace with nucleophile (minus H)

STEREOCHEMISTRY:
Racemic (optically inactive)

SOLVENT: Polar
Water most polar

46
Q

E1

A

REACTION STABILITY: 3° 2° 1° ( controlled by cation stability)
I>Br>Cl
C> N>O>F
decrease vertical down periodic table

RECOGNITION:
A. Neural nucleophile
B. 3° or 2°

PREDICTING PRODUCT: remove halide and a HYDROGEN from a neighboring carbon. Can be cis/tran

STEREOCHEMISTRY:
Eliminate hydrogen

Mech: must show carbocation formation

SOLVENT:
Polar



47
Q

How to draw SN2 Reaction 

A
  1. Don’t change the structure for the carbon skeleton
  2. Put the nuclear feel in the exact spot where the halide is. Unless it was attached to a chiral center. IN THAT CASE INVERT THE STRUCTURE
  3. Don’t mess with the spectators 
48
Q

How to draw SN1 reaction 

A
  1. Don’t change the structure of the carbon skeleton
  2.  Connect the carbon and Z. While taking off halide (Br) from the nucleophile 
  3. If halide (Br,Cl,I) is attached to chiral center, a racemic mixture is formed
  4. Carbocation formation is SLOW STEP
49
Q

What are the leaving groups?

A

R—I> R—BR>R—Cl

Anesthesia Interview Review (5 decks)

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