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

Organic Chemistry Pt 2 - Week 19 - 20 Flashcards

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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:

A

tertiary alcohol –> Reflux —> NO REACTION

21
Q

What are the conditions for reflux?

A

H2SO4

CrO42- / Cr2O72-

22
Q

How are alkyl chlorides formed using SOCl2?

A

C2H5OH + SOCl2 —-> C2H5Cl + SO2 + HCl

23
Q

How are alkyl bromides formed using PBr3?

A

3 C2H5OH + PBr3 —-> 3 C2H5Br + H3PO3

24
Q

How are metal alkoxides formed?

A
  • similar to reaction of reactive metals with
    water

2M + 2 H2O –> 2 MOH + H2

25
Q

What forms after the dehydration of alcohols?

A

Alcohols + heat –> (conc H2SO4 or H3PO4) and reflux –> alkenes

26
Q

What occurs in the deprotonation of alcohols?

A

Acid - Base reaction to form an alkoxide

R-OH + B: - < —> R - O- + BH

27
Q

What are the physical properties (state, miscibility, density and intermolecular forces) of aldehydes/ketones?

A

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
Q

What is cyanohydrin formation?

A

Addition of HCN to a carbonyl

CH3COCH3 –> (KCN H2SO4) –>
CH3COHCCNCH3

29
Q

What is cyclic hemiacetal formation?

A
  • how sugars convert from linear to ring
    conformation
  • Cyclic hemiacetals are stable and isolable
    (capable of being isolated or disjointed)
30
Q

What is imine formation?

A

How primary amines and ammonia react with carbonyls

CH3COCH3 + CH3-NH2 ——> CH3CN(CH3)CH3 + H2O

31
Q

Why does alpha carbon deprotonate?

A

Alpha carbon has relatively acidic C-H bonds (pKa ~ 20) —> easy to deprotonate for an additional reactivity center

32
Q

What conditions does deprotonation of alpha carbon occur?

A

Can deprotonate under both acidic (enol) and basic (enolate) conditions.

33
Q

How does Grignard reagents form?

A

Formed when certain metals are added to alkyl halides

C4H9Br —-> (Mg metal) (Et2O or THF) –>
C4H9MgBr

34
Q

What are the trends in the states of matter of acid chlorides and esters?

A
  • Acids, acid chlorides, esters - usually liquids
    at RT
  • Amides and anhydrides usually solids at RT
35
Q

What are the trends in the density of acid chlorides and esters?

A

Esters are less dense than water

36
Q

What are the trends in miscibility of acid chlorides and esters?

A
  • 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
Q

What are the trends in boiling point of acid chlorides and esters?

A
  • Trend depends on intermolecular forces
    possible.
  • Increases with chain length
  • Affected by branching
38
Q

What intermolecular forces are present in acid chlorides and esters and anhydrides?

A

Dipole-dipole and Van der Waal forces

  • can accept hydrogen bonds from a polar
    protic solvent
39
Q

What intermolecular forces are present in carboxylic acids and amides?

A

Hydrogen bonding, Dipole-dipole and Van der Wall forces

40
Q

Which reagents work in the reduction of acid chlorides?

A
  • LAH (excess) - H3O+

and

  • NaBH4 (excess) - H30+
41
Q

What happens when you add multiple equivalents of Grignard or Organolithium reagents to an ester?

A

= tertiary alcohol and R’ - OH forms

42
Q

What happens when you add multiple equivalents of Grignard or Organolithium reagents to an acid chloride?

A

= a tertiary alcohol and HCl

43
Q

What happens when you add multiple equivalents of Grignard or Organolithium reagents to an acid anhydride?

A

= a tertiary alcohol and a tertiary alcohol

44
Q

What happens to organometallic /grinyard reagents in the presence of protic N-H or O-H bonds?

A

They act like a base and get protonated

45
Q

What are the states of matter, miscibility and density of amines?

A

State - Usually liquids or solids at RT
Miscibility - Small amines (< 5-6 carbon atoms) are miscible with water
Density - Less dense than water

46
Q

What intermolecular forces are present within amines?

A

Hydrogen bonding, Dipole-dipole, Van der Waal

47
Q

What are the trends in boiling point of amines?

A

As chain length increases boiling point increases.

As the amide group becomes more branched boiling point decreases.

48
Q

What are the trends in reactivity of amines?

A
  • Amines are both nucleophilic and a weak
    base
  • They will be protonated by acids

Chemistry (10 decks)

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