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Fundamnetals of Chemistry for Biochemsists CHE00031C > Organic Structures and Mechanisms 2 > Flashcards

Organic Structures and Mechanisms 2 Flashcards

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1
Q

“Me” abbreviation meaning

A

-CH3 Methyl

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2
Q

“Et” abbreviation meaning

A

-CH2CH3 Ethyl

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3
Q

“Pr” abbreviation meaning

A

-CH2CH2CH3 Propyl

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4
Q

“iPr” abbreviation meaning

A

-CH(CH3)2 Iso-propyl

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5
Q

“Bu” abbreviation meaning

A

-CH2CH2CH2CH3 Butyl

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6
Q

“tBu” abbreviation meaning

A

-C(CH3)3 tert-butyl

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7
Q

“Ph” abbreviation meaning

A

Phenyl

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8
Q

“R” abbreviation meaning

A

Any alkyl group

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9
Q

“Ar” abbreviation meaning

A

Any aromatic of substituted aromatic

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10
Q

Define heteroatom

A

Anything not carbon

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11
Q

What is a functional group level?

A

The no. bonds to heteroatoms from a given C atom

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12
Q

What is an oxidation reaction?

A

gain of O2 OR loss of H2 OR loss of e-

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13
Q

What is a reduction reaction?

A

gain of H2 OR loss of O2 OR gain of e-

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14
Q

Define inductive effects

A

The way in which the electronegative atoms polarize e- density in the single bond framework of a molecule

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15
Q

What does a -I effect mean?

A

e- withdrawing

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16
Q

What does a +I effect mean

A

e- donating

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17
Q

is -X -I or +I?

A

-I

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18
Q

is -CX3 -I or +I?

A

-I

19
Q

is C=O -I or +I?

A

-I

20
Q

is C-Li -I or +I?

A

+I

21
Q

is C-Mg -I or +I?

A

+I

22
Q

is C-CH3 -I or +I?

A

+I

23
Q

is C-R -I or +I?

A

+I

24
Q

What is heterolytic bond cleavage?

A

Forms a cation and an anion

25
Q

What is homolytic bond cleavage?

A

Forms a radical

26
Q

How does the size of an energy barrier for a reaction affect the rate of reaction?

A

Smaller energy barrier = faster reaction

27
Q

What determines the size of the energy barrier to a reaction?

A

Depends on energy of the intermediate
- stable intermediates reduce the energy barrier

28
Q

Define mesomeric effects (resonance)

A

The movement of e- density within the double bond/lone pair system of a molecule by resonance conjunction

29
Q

Which takes dominates? inductive or mesomeric effects?

A

Mesomeric

30
Q

What are hyperconjuction effects?

A

When there is a carbocation, an adjacent C-H or C-C bond can partially overlap with the carbocations empty orbital, donating a small amount of e- density to the empty orbital (a lot weaker than normal resonance)

31
Q

Basic rules for organic mechanisms

A

1) Electron flow must start from an electron rich site
2) Flow must move towards and electron poor site
3) Ensure that nothing has too many bonds
4) Balance charges
5) Repeat if possible/needed

32
Q

Define nucleophile (Nu-)

A

Electron rich species that will react with C+ or C delta +

33
Q

Define base (B:)

A

Electron rich species that will react with H+ or H delta +

34
Q

Define electrophile (E+)`

A

Electron poor species (usually C+ or C delta +) that reacts with a nucleophile

35
Q

Define acid (H+)

A

Electron poor H+ pr H delta + that will react with a base

36
Q

Define chemoselectivity

A

When several diff. sites could react, one does so with preferance

37
Q

How do you choose which site to prioritize in mechanisms for the e- rich site?

A
  • Less electronegative is BETTER (more willing to donate electrons)
    I- > Br- > Cl- > F-
    R-NH2 > R-OH&raquo_space; R-F
  • More resonance is WORSE
  • Steric hinderance is bad for nucleophiles
    (ie. a tertiary alcohol is worse than primary)
38
Q

How do you prioristise sites for choosing the electron poor site?

A
  • High -I effect is good
  • High +M is bad
  • Resonance dominates inductive effect
39
Q

What is regioselectivity?

A

When multiple parts of a functional group could react but one is prefered

40
Q

Examples of an e- rich site

A

1) Negative charge
2) Lone pair
3) Double bond
4) Single bond

41
Q

Examples of e- poor site

A

1) carbocation/H+
2) Atom adjacent to positive charge on heteroatom
3) Onward towards a positive charge
4) Partially positive charge
5) Partially positive charge at an alternating distance

42
Q

How do you prioritize an intermediate product?

A

You want a more stable intermediate (ie. the carbocation is bonded to more carbons)

43
Q

Criteria for most acidic site

A
  • Generates the most stable conjugate base
  • Negative charges should be on the most electronegative atoms
44
Q

Criteria for most basic site

A
  • Greatest electron density
  • Most able to donate e- (lone pairs/negative charges should be localized, less electronegative atoms can more easily donate e- denisty)

Fundamnetals of Chemistry for Biochemsists CHE00031C (5 decks)

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