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organic II Flashcards

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1
Q

What is the Sn2 mechanism?
Draw example mechanism.

A

Nucleophillic substitution with two species involved in the rate determining step and 2nd order.
Includes a transition state.
Page. 174

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2
Q

What is the Sn1 mechanism?
Draw example mechansim.

A

Nucleophillic substitution with one species involved in the rate determining step and first order.
Includes a carbocation with a planar shape.
Equal chance of nucleophile attacking from left or right so 2 products formed: a racemic mixture.
Page. 175

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3
Q

How to form an achohol from an aldehyde or ketone?

A

Reduction of aldehyde/ ketone using LiAlH4 (lithium aluminium hydride) and dry ether solvent.

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4
Q

How can you identify an aldehyde? (4 ways)

A
  • Acidified potassium dichromate (VI) - orange sol to green sol.
  • Fehling’s solution - deep blue sol to red precip
  • Benedict’s solution - deep blue sol to red precip
  • Tollen’s reagent - colourless sol to silver mirror
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5
Q

How can you identify a ketone?

A
  • React with iodine - yellow precip
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6
Q

Reaction of carbonyl compound with KCN and mechanism.

A
  • Nucleophillic addition
  • Produces Hydroxynitrile racemic mixture
    page. 180
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7
Q

How to test for carbonyl compound?

A
  • Brady’s reagent (2,4-DNPH) - forms orange precip
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8
Q

How to form a carboxylic acid by hydrolysis?

A
  • Hydrolysis of nitrile - heat under reflux and dilute acid/ aqueous alkali
  • equation on page. 184
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9
Q

How can you reduce a carboxylic acid?

A
  • LiAlH4 reducing agent and solvent of dry ether
  • Produces a primary alcohol and water
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10
Q

How can you neutralise a carboxylic acid and what is the product?

A
  • mixing with aqueous alkali
  • makes sodium X-oate
  • equation on page. 185
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11
Q

Halogenation of a carboxylic acid.

A
  • PCl5 (phosphorus (V) chloride)
  • Forms an acyl chloride
  • equation on page. 185
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12
Q

Esterification of a carboxylic acid.

A
  • Carboxylic acid is mixed with an alcohol and a small amount of acid catalyst (usually conc. sulfuric acid)
  • Forms an ester and water
  • equation on page. 185
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13
Q

What happens when you react an acyl chloride with water?

A
  • Forms a carboxylic acid and hydrogen chloride gas (misty fumes)
  • equation on page. 186
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14
Q

What happens when you react an acyl chloride with an alcohol?

A
  • Forms an ester and hydrogen chloride gas (misty fumes)
  • equation on page. 186
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15
Q

What happens when you react an acyl chloride with conc. ammonia?

A
  • Forms an amide and hydrogen chloride gas (misty fumes)
  • HCl then reacts with NH3 (as acid and base) to form ammonium chloride
  • equation on page. 187
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16
Q

What happens when you react an acyl chloride with an amine?

A
  • Forms an N-substituted amide and hydrogen chloride gas (misty fumes)
17
Q

Hydrogenation on benzene.

A
  • Mix benzene with hydrogen, heating under pressure and nickel catalyst to form cyclohexane
  • equation on page. 196
18
Q

Combustion of benzene.

A
  • Smoky flame
  • equation on page. 196
19
Q

Bromination of benzene.
Mechanism.

A
  • Bromine and benzene are heated under reflux in the presence of a catalyst: halogen carrier (usually aluminium chloride or bromide) but iron filings in this reaction
  • Forms bromobenzene and HBr
  • equation on page. 196
20
Q

Nitration of benzene
Mechanism.

A
  • Warming benzene with conc. nitric acid and sulfuric acid
  • Forms nitrobenzene and water
  • equation on page. 196
21
Q

Friedel crafts alkylation of benzene.
Mechanism.

A
  • Halogenoalkane with halogen carrier (AlCl3)
  • Forms alkylbenzene and hydrogen halide
  • equation on page. 197
22
Q

Friedel crafts acylation of benzene.
Mechanism.

A
  • Acyl chloride and halogen carrier (AlCl3)
  • Forms ketone and hydrogen halide
  • equation on page. 197
23
Q

Bromination of phenol

A
  • Room temp without catalyst with bromine water
  • bromine water is decolourised to form a white precipitate
  • equation on page. 200
24
Q

How to form an amine from a halogenoalkane?

A
  • heating halogenoalkane with ammonia (nucleophile) under pressure and in a sealed container or mixed with conc. aqueous ammonia
  • forms alkyl amine and hydrogen chloride
  • alkyl amine acts as a nucleophile reacting with halogenoalkane to form a secondary amine and HCl
  • ammonia used in excess to avoid unwanted side-reactions, some of excess ammonia reacts with HCl to form NH4Cl
  • equation on page. 202
25
Q

Reduction of a nitrile.

A
  • Reduction of nitrile using LiAlH4 in dry ether
  • Forms amine
  • equation on page. 203
26
Q

Reduction of nitrobenzene.

A
  • Tin as reducing agent mixed with conc. HCl acid and heat under reflux
  • forms phenylamine and water
  • equation on page. 203
27
Q

Reaction of amine and ethanoyl chloride and what type of reaction?

A
  • addition-elimination reaction
  • forms N-…yl ethanamide and HCl
28
Q

How to make a grignard reagent.

A
  • Heat under reflux the chosen halogenoalkane and magnesium in dry ether solvent - organometallic compount containing magnesium
    e.g. R - Br + Mg —> R-Mg-Br
29
Q

How to make a carboxylic acid using a grignard reagent.

A
  • RMgBr reacts with CO2
    1. form grignard reagent
    2. react with CO2
    3. hydrolysis using dilute acid
  • equation on page. 216
30
Q

How to make a primary alcohol using a grignard reagent.

A
  • RMgBr reacts with methanal
    1. form grignaard reagent
    2. react with methanal
    3. hydrolysis using dilute acid
  • equation on page. 216
31
Q

How to make a secondary alcohol using a grignard reagent.

A
  • RMgBr reacts with aldehyde
    1. form grignaard reagent
    2. react with aldehyde
    3. hydrolysis using dilute acid
  • equation on page. 217
32
Q

How to make a tertiary alcohol using a grignard reagent.

A
  • RMgBr reacts with ketone
    1. form grignaard reagent
    2. react with ketone
    3. hydrolysis using dilute acid
  • equation on page. 217
33
Q

3 differences between making esters with ethanoyl chloride and ethanoic acid.

A

-The reaction is irreversible compared to reversible
-Hydrogen chloride is the by-product rather than water
-The reaction is very fast/occurs at room temperature so
an acid catalyst is not needed

34
Q

Phenylamine can be prepared from nitrobenzene.
Butylamine can be prepared from butanenitrile.
Compare and contrast these two preparations of amines.

A

-Both are reduction reactions
-Reagents for preparation of phenylamine
are tin and conc. hydrochloric acid
-Reagents for preparation of butylamine are
either Hydrogen gas and nickel catalyst
or
lithium tetrahydridoaluminate(III) and dry ether

Chemistry (5 decks)

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