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MCAT- Organic CHem > Class 1 > Flashcards

Class 1 Flashcards

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1
Q

What is a DOU?

A

Degree of unsaturation

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2
Q

How do you measure a DOU?

A

One double, triple or ring is = to one pi bond

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3
Q

How do we treat Halogens, N and O in counting DOU?

A

Halogen treat as an extra H
N subtract the number of N from the number of Hs
O ignore

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4
Q

Whats the relationship between energy and stability?

A

Increase in energy decreases stability

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5
Q

What are the characteristics of a molecule that is unstable?

A

Increased energy
Reactive
Decrease lifetime

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6
Q

What are the characteristics of a molecule that is stable?

A

Decreased energy
Less reactive
Increase lifetime

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7
Q

What is ring strain?

A

Destabilization of of ring weakens the C–C bonds and increases reactivity

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8
Q

What are examples of e- withdrawing and donating?

A

Withdrawing: O and Halogens

Donating: Alkyl groups

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9
Q

What is the order of electronegativity?.

A

F O N Cl Br I S C H

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10
Q

What is the order of strongest Carbocations?

A

(Most stable) 3>2>1>Mehtyl (least stable)

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11
Q

What is the order of strongest Carbanions?

A

(Most reactive) 3>2>1>Methyl (least reactive)

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12
Q

What are the 3 things that resonance contributors have

A
  1. Octet rule
  2. Least formal charge
    • charge on more electronegative element
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13
Q

What is the relationship between acids and bases?

A

Stronger the acid the weaker the conjugate base

More stable the conjugate base the stronger the acid

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14
Q

What are the factors influencing acidity by alternating conjugate stability?

A
  1. Electronegativity: more electronegative holds charge better
  2. Resonance: increases stability of anionic conjugate base
  3. Induction: Depends on proximity to electronegativity
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15
Q

What us a Nu-?

A

Nucleus loving
Have a full or partial - charge
Donates e- (Lewis base)

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16
Q

What are some good Nu-?

A

OH-, Br-, Cl-, OR-, H2O, NH2-, NH3

17
Q

What effect does size, electronegativity and charge have on Nu-?

A

Increase size increases Nu- strength
Decrease electronegativity increases Nu- strength
- charge increase Nu- strength

18
Q

What are E+?

A

e- loving
Accepts e- pair (Lewis acid)
Has full or partial + charge

19
Q

What makes a good leaving group?

A 
Resonance stabilized LG
Weak Base (Cl
20
Q

What makes a bad leaving group?

A 
Strong bases (OH-, RO-,NH2-)
Acid Catalysts (Protonation)
21
Q

What are ugly leaving groups?

A

H- or C- are almost never LGs

22
Q

What does RICE stand for for making molecules more stable?

A

Resonance
Induction
Size
Electronegativity

23
Q

What are isomers?

A

Different compound with the same molecular formula

24
Q

What are structural (constitutional) isomer?

A

Different atomic connectivity

Different chemical and physical properties

25
Q

What are conformational isomers?

A

Different by rotation around the the sigma bond
Same chemical and physical properties
Same atomic connectivity

26
Q

What are the 3 position in conformational isomers and their stabilities?

A

Anti: Most stable
Gauche: Intermediate
Syn: Eclipsed, most unstable

27
Q

What is chirality?

A

Non-superimposable on mirror image

No plane of symmetry

28
Q

What are the characteristics of a chiral centre?

A

sp3
tetrahedral
4 Different groups

29
Q

What are the 2 forms of optical activity?

A

d+: clockwise

d-: counterclockwise

30
Q

What are Stereoisomers?

A

Different spatial arrangement

31
Q

What are enantiomers?

A

Non-superimposable
Opposite configuration at all chiral centres
Same physical and chemical properties

32
Q

What is a racemic mixture?

A

1:1 R and S

optically inactive

33
Q

What are diasteriomers?

A

Non-superimposable
At least 1 chiral centre is the same (need 2 or more)
Different physical and chemical properties

34
Q

What are geometric isomers?

A

Double bond or ring structures
Different chemical and physical properties
No chiral center
(Z and E)

35
Q

What is an epimer?

A

Diasteriomer that differs in only 1 chiral centre

36
Q

What is a mess compound?

A

Plane of symmetry and even the number of chiral centres must have opposite configurations
Not optically active

MCAT- Organic CHem (2 decks)

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