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Advanced Higher Chemistry Organic > Synthesis > Flashcards

Synthesis Flashcards

1
Q

Homolytic fission

A

Results in two neutral free radicals. Non-polar covalent bonds break. The covalent bond breaks evenly and electrons are distributed equally between the atoms.

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2
Q

Is homolytic fission ideal for organic synthesis?

A

Reactions involving homolytic fission tend to result in the formation of very complex
mixtures of products, making them unsuitable for organic synthesis.

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3
Q

Heterolytic fission

A

Results in two oppositely charged ions. Polar bond breaks unevenly and one atom receives the electron pair.

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4
Q

Is heterolytic fission ideal for organic synthesis?

A

Reactions involving heterolytic fission tend to result in far fewer products than reactions involving homolytic fission, and so are better suited for organic synthesis.

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5
Q

two single-headed arrows starting at the middle of a covalent bond indicate…

A

homolytic bond fission is occurring.

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6
Q

a double-headed arrow starting at the middle of a covalent bond indicates…

A

heterolytic bond fission is occurring.

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7
Q

In reactions involving heterolytic bond fission, attacking groups are classified as…

A

nucleophiles or electrophiles.

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8
Q

Nucleophiles

A

-Negatively charged ions or neutral molecules that are electron rich (Ammonia and water)
-Attracted to regions of partial or fully positive charge.
-Donates an electron pair to form a covalent bond.

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9
Q

Electrophiles

A

-Positively charged ions or neutral molecules that are electron deficient (SO3)
-Attracted to regions of partial or fully negative charge.
-Accepts electron pairs to form a covalent bond

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10
Q

Haloalkanes (alkyl halides)

A

substituted alkanes in which one or more of the hydrogen atoms is replaced with a halogen atom.

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11
Q

How are monohaloalkanes classified?

A

can be classified as primary, secondary or tertiary according to the number of alkyl
groups attached to the carbon atom containing the halogen atom.

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12
Q

Monohaloalkanes undergo elimination reactions to form…?

A

alkenes

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13
Q

Monohaloalkanes elimination reaction catalyst

A

a strong base, such as
potassium or sodium hydroxide in ethanol

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14
Q

Why haloalkanes undergo nucleophilic substitution?

A

Their electronegativity puts a partial positive charge on a carbon atom.

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15
Q

Haloalkane + CN-

A

Nitrile - Can be hydrolysed to form a carboxylic acid

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16
Q

Haloalkane + Aqueous alkali (eg. NaOH)

A

Alcohol

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17
Q

Haloalkane + NH3

A

Amine

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18
Q

Haloalkane + Alkoxide (-O-CH3)

A

Ether

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19
Q

How can an alkoxide be prepared?

A

By reacting methanol with sodium or other alkali metal.

20
Q

Why do benzene rings undergo electrophilic substitution?

A

Very stable molecule. Undergoes ES as it resists addition reactions.

21
Q

Halogenation

A

C6H6 + Cl2 +FeCl3 cat => C6H5Cl

22
Q

Nitration

A

C6H6 + HNO3 + H2SO4 cat => C6H5NO2

23
Q

Sulfonation

A

C6H6 + SO3 + CONC H2SO4 => C6H5SO3H

24
Q

Alkylation

A

C6H6 + R-Cl + AlCl3 => C6H5-R

25
Q

SN1

A

is a nucleophilic substitution reaction with one species in the rate determining step
and occurs in a minimum of two steps via a trigonal planar carbocation intermediate.

26
Q

SN2

A

is a nucleophilic substitution reaction with two species in the rate determining step and occurs in a single step via a single five-centred, trigonal bipyramidal transition state.

27
Q

Reducing aldehydes and ketones using lithium aluminium hydride produces…

A

alcohol

28
Q

Ethers and bpt

A

Due to the lack of hydrogen bonding between ether molecules, they have lower boiling points than the corresponding isomeric alcohols.

29
Q

Ethers and solubility

A

Methoxymethane and methoxyethane are soluble in water. Larger ethers are insoluble in water due to their increased molecular size

30
Q

Why are ethers used as solvents?

A

Ethers are commonly used as solvents since they are relatively inert chemically and will
dissolve many organic compounds

31
Q

Markovnikov’s rule

A

states that when a hydrogen halide or water is added to an
unsymmetrical alkene, the hydrogen atom becomes attached to the carbon with the most hydrogen atoms attached to it already.

32
Q

hydrolysing nitriles, esters or amides…

A

gives a carboxylic acid

33
Q

oxidising primary alcohols using acidified permanganate, acidified dichromate and hot copper(II) oxide

A

gives a carboxylic acid

34
Q

oxidising aldehydes using acidified permanganate, acidified dichromate, Fehling’s solution and Tollens’ reagent

A

gives a carboxylic acid

35
Q

Amines

A

Amines are organic derivatives of ammonia in which one or more hydrogen atoms of
ammonia has been replaced by an alkyl group. Amines react with acids to form salts.

36
Q

Amines and bpts

A

Primary and secondary amines, but not tertiary amines, display hydrogen bonding. As a result, primary and secondary amines have higher boiling points than isomeric tertiary
amines.

37
Q

Amines and solubility

A

Primary, secondary and tertiary amine molecules can hydrogen-bond with water molecules, thus explaining the appreciable solubility of the shorter chain length amines in water.

38
Q

Aldehyde

A

O
||
R-C-H

39
Q

Ketone

A

O
||
R-C-R’

40
Q

Ester

A

O
||
R-C-OR’

41
Q

Amine

A

R-NH2

42
Q

Ether

A

R-O-R’

43
Q

Elimination of H-X catalyst

A

NaOH in ethanol

44
Q

Dehydration catalyst

A

Al2O3/CONC H2SO4 H3PO4

45
Q

Examples of nucleophiles

A

Cl- Br- OH- CN- NH3 and H2O

46
Q

Examples of electrophiles

A

H+ NO2+ and SO3

47
Q

Oxidising agents

A

Hot CuO, Acidified dichromate, Fehlings solution, tollens solution

Advanced Higher Chemistry Organic (3 decks)

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