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Chemistry > Organic Chemistry Pt 2 - Week 19 - 20 > Flashcards

Organic Chemistry Pt 2 - Week 19 - 20 Flashcards

(48 cards)

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1
Q

What directing effect does a negative charge cause?

A

Negative charge concentrates at ortho and para positions

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2
Q

What directing effect does a positive charge cause?

A

Positive charge concentrates at ortho and para positions

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3
Q

What are some examples of strongly activating ortho-para directors?

A

-NH2, , -NHR, -NR2, -OH, -NHR, -O2CR

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4
Q

What are some examples of weakly activating ortho-para directors?

A

-C6H5, -CH3, -CH(CH3)2, -R, -CH2CH3,
-F, -Cl, -BR, -I

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5
Q

What are some examples of weakly deactivating meta directors?

A

-CHO, -COR, -SO3H, -CO2H, -CO2R

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6
Q

What are some examples of strongly deactivating meta directors?

A

-CN, -NH(CH3)3 -NO2

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7
Q

What pushes lone pairs into the ring by resonance?

A

Ortho-para directors

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8
Q

What can pull electrons out of the ring by resonance?

A

Meta directors

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9
Q

What is oxidation?

A

Loss of hydrogen (electrons) and gain of oxygen

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10
Q

What is reduction?

A

Loss of oxygen and gain of hydrogen (electrons)

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11
Q

What are oxidising agents?

A

Reagents that oxidise C atoms by adding O atoms
Have lots of oxygen and an atom at a high oxidation state.

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12
Q

What are reducing agents?

A

Reagents that reduce C atoms by adding H atoms

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13
Q

Why is knowing the pKa of an organic molecule usefull?

A

It is useful for predicting state of functional groups in a reaction mixture

pH > pKa basic form pH < pKa acidic form

Helps predict reactivity for unknown or unfamiliar mechanisms

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14
Q

What is the general formula of alcohols?

A

CnH2n+1OH

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15
Q

What are the physical properties of the state, density and intermolecular forces of alcohols?

A

State - usually liquids or solids at RT
Density - less dense than water
Intermolecular forces - Hydrogen bonding,
Dipole-Dipole, Van der Waal

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16
Q

Explain the boiling point of alcohols?

A
  • Higher than hydrocarbons and alkyl halides
    of similar chain length
  • Increases with chain length
  • Affected by branching
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17
Q

Explain the miscibility of alcohols:

A
  • Alcohols are generally miscible with organic
    solvents
  • Short alcohols ~ 3-4 carbon atoms are fully
    miscible in water
  • Dependent on branching
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18
Q

What and how are primary alcohols oxidised to?

A

Primary alcohol –> Distillation to aldehyde

Primary alcohol –> Reflux –> Carboxylic acid
H2SO4 CrO42-

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19
Q

Explain the oxidation of secondary alcohols:

A

secondary alcohol –> reflux —-> ketone
H2SO4 CrO42-

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20
Q

Explain the oxidation of tertiary alcohols:

Study These Flashcards
A

tertiary alcohol –> Reflux —> NO REACTION

21
Q

What are the conditions for reflux?

Study These Flashcards
A

H2SO4

CrO42- / Cr2O72-

22
Q

How are alkyl chlorides formed using SOCl2?

Study These Flashcards
A

C2H5OH + SOCl2 —-> C2H5Cl + SO2 + HCl

23
Q

How are alkyl bromides formed using PBr3?

Study These Flashcards
A

3 C2H5OH + PBr3 —-> 3 C2H5Br + H3PO3

24
Q

How are metal alkoxides formed?

Study These Flashcards
A
  • similar to reaction of reactive metals with
    water

2M + 2 H2O –> 2 MOH + H2

25
What forms after the dehydration of alcohols?
Alcohols + heat --> (conc H2SO4 or H3PO4) and reflux --> alkenes
26
What occurs in the deprotonation of alcohols?
Acid - Base reaction to form an alkoxide R-OH + B: - < ---> R - O- + BH
27
What are the physical properties (state, miscibility, density and intermolecular forces) of aldehydes/ketones?
State - usually solid or liquid at RT Miscibility - generally miscible with organic solvents - short chains miscible in water - dependent on branching Density - less dense that water Intermolecular forces - Dipole-Dipole, Van der Waal Boiling point - Higher than hydrocarbons and alkyl halides of similar chain length - Increases with chain length - Affected by branching
28
What is cyanohydrin formation?
Addition of HCN to a carbonyl CH3COCH3 --> (KCN H2SO4) --> CH3COHCCNCH3
29
What is cyclic hemiacetal formation?
- how sugars convert from linear to ring conformation - Cyclic hemiacetals are stable and isolable (capable of being isolated or disjointed)
30
What is imine formation?
How primary amines and ammonia react with carbonyls CH3COCH3 + CH3-NH2 ------> CH3CN(CH3)CH3 + H2O
31
Why does alpha carbon deprotonate?
Alpha carbon has relatively acidic C-H bonds (pKa ~ 20) ---> easy to deprotonate for an additional reactivity center
32
What conditions does deprotonation of alpha carbon occur?
Can deprotonate under both acidic (enol) and basic (enolate) conditions.
33
How does Grignard reagents form?
Formed when certain metals are added to alkyl halides C4H9Br ----> (Mg metal) (Et2O or THF) --> C4H9MgBr
34
What are the trends in the states of matter of acid chlorides and esters?
- Acids, acid chlorides, esters - usually liquids at RT - Amides and anhydrides usually solids at RT
35
What are the trends in the density of acid chlorides and esters?
Esters are less dense than water
36
What are the trends in miscibility of acid chlorides and esters?
- Very few amides are soluble miscible in water - Esters are soluble/miscible in water - Shorter chain carboxylic acids are miscible in water - Acid chlorides and anhydrides react in water so are incompatible
37
What are the trends in boiling point of acid chlorides and esters?
- Trend depends on intermolecular forces possible. - Increases with chain length - Affected by branching
38
What intermolecular forces are present in acid chlorides and esters and anhydrides?
Dipole-dipole and Van der Waal forces - can accept hydrogen bonds from a polar protic solvent
39
What intermolecular forces are present in carboxylic acids and amides?
Hydrogen bonding, Dipole-dipole and Van der Wall forces
40
Which reagents work in the reduction of acid chlorides?
- LAH (excess) - H3O+ and - NaBH4 (excess) - H30+
41
What happens when you add multiple equivalents of Grignard or Organolithium reagents to an ester?
= tertiary alcohol and R' - OH forms
42
What happens when you add multiple equivalents of Grignard or Organolithium reagents to an acid chloride?
= a tertiary alcohol and HCl
43
What happens when you add multiple equivalents of Grignard or Organolithium reagents to an acid anhydride?
= a tertiary alcohol and a tertiary alcohol
44
What happens to organometallic /grinyard reagents in the presence of protic N-H or O-H bonds?
They act like a base and get protonated
45
What are the states of matter, miscibility and density of amines?
State - Usually liquids or solids at RT Miscibility - Small amines (< 5-6 carbon atoms) are miscible with water Density - Less dense than water
46
What intermolecular forces are present within amines?
Hydrogen bonding, Dipole-dipole, Van der Waal
47
What are the trends in boiling point of amines?
As chain length increases boiling point increases. As the amide group becomes more branched boiling point decreases.
48
What are the trends in reactivity of amines?
- Amines are both nucleophilic and a weak base - They will be protonated by acids

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