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Chemistry (personal) > Topic 17 > Flashcards

Topic 17 Flashcards

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1
Q

SN1 reactions

A

Nucleophilic substitution reactions
Tertiary halogenoalkanes and a nucleophile
2 step reaction (intermediate formed)
Both enantiomers formed, racemic mixture, no optical activity

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2
Q

SN2 reactions

A

Nucleophilic substitution reactions
Primary halogenoalkanes and a nucleophile
1 step reaction
1 enantiomer formed, optical activity

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3
Q

Tests for oxidation (3)

A

Acidified potassium dichromate solution (orange to green)
Fehling’s or Benedict’s solution (blue solution to red precipitate)
Tollens’ reagent (colourless solution to silver mirror)
For all: Heat in water bath

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4
Q

Test for a carbonyl compound (aldehyde or ketone only)

A

Brady’s reagent

Forms a bright orange precipitate

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5
Q

Test for CH3-CO group

A

Alkaline solution of iodine
Warmed and cooled
Yellow precipitate formed (CHI3)
Triiodomethane reaction

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6
Q

Formation of a hydroxynitrile

A

Reagents: carbonyl compound, hydrogen cyanide
Conditions: aqueous alkaline solution containing KCN
Products: hydroxynitrile
Observations: product is a racemic mixture
Reaction: nucleophilic addition

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7
Q

Ethanoic acid and sodium reaction (simple)

A

Sodium ethanoate (ionic) and hydrogen

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8
Q

Ethanoic acid and sodium hydroxide reaction (simple)

A

Sodium ethanoate (ionic) and water

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9
Q

Ethanoic acid and sodium carbonate reaction (simple)

A

Sodium ethanoate (ionic) and water and carbon dioxide

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10
Q

Carboxylic acid and ammonia reaction (simple)

A

eg. ammonium ethanoate (ionic)

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11
Q

Carboxylic acid and amine reaction (simple)

A

eg. methylammonium ethanoate (ionic)

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12
Q

Reduction of a carboxylic acid

A 
Reactants: carboxylic acid, reducing agent LiAlH4
Conditions: solvent = dry ether
Products: primary alcohol and water
Observations:
Reaction:
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13
Q

Halogenation of a carboxylic acid

A 
Reactants: carboxylic acid, PCl5
Conditions: anhydrous, no heat
Products: acyl chloride, POCl3, HCl (g)
Observations: HCl = misty fumes, separate products by fractional distilation
Reaction:
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14
Q

Esterification of a carboxylic acid

A 
Reactants: carboxylic acid, alcohol
Conditions: acid catalyst (conc. H2SO4)
Products: ester (alcohol-acid), water
Observations:
Reaction: condensation
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15
Q

Forming carboxylic acids by oxidation

A 
Reactants: primary alcohol, excess acidified potassium dichromate solution
Conditions: heat under reflux
Products: carboxylic acid, water
Observations: orange to green
Reaction: oxidation
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16
Q

Hydrolysis of nitriles

A

Acid:
Reactants: nitrile, water, HCl
Products: carboxylic acid, ammonium chloride
Note: in equilibrium, lower yield

Alkaline:
Reactants: nitrile, water, sodium hydroxide
Products: salt eg. sodium ethanoate, NH2
Note: react salt with acid to form carboxylic acid

Conditions for both: Heat under reflux!!

17
Q

Formation of an acyl chloride

A 
Reactants: carboxylic acid, PCl5
Conditions: anhydrous, no heat
Products: acyl chloride, POCl3, HCl (g)
Observations: HCl = misty fumes, separate products by fractional distilation
Reaction: halogenation
18
Q

Acyl chloride and water reaction

A 
Reactants: acyl chloride, water
Conditions:
Products: carboxylic acid and HCl
Observations: HCl = misty fumes
Reaction: condensation
19
Q

Acyl chloride and alcohol reaction

A 
Reactants: acyl chloride, alcohol
Conditions: room temp
Products: ester, HCl
Observations: HCl = misty fumes
Reaction: condensation
20
Q

Acyl chloride and concentrated ammonia

A

Reactants: acyl chloride, concentrated ammonia
Conditions:
Products: amide, HCl
Observations: HCl reacts with ammonia forming ammonium chloride (white smoke)
Reaction:

21
Q

Acyl chloride and primary amine

A 
Reactants: acyl chloride, primary amine
Conditions:
Products: N-substituted amide, HCl
Observations: HCl reacts with amine forming RNH3+Cl- salt (white smoke)
Reaction:
22
Q

Hydrolysis of esters

A

Acidic:
Reactants: ester, water, moderately concentrated acid catalyst
Products: carboxylic acid, alcohol
Note: reversible, low yield

Alkaline:
Reactants: ester, sodium hydroxide
Products: salt, alcohol
Note: react salt with acid to form carboxylic acid

23
Q

Explain chiral

A

Asymmetric C atom joined to 4 different groups

2 non-superimposable mirror images (optical isomers)

24
Q

Why a hydroxynitrile formed in nucleophilic addition has no optical activity

A

Trigonal planar carbonyl compound
Equal chance of CN attacking from either side of the molecule
Racemic mixture formed

25
Q

Racemic mixture

A

Equimolar mixture of two enantiomers tat has no optical activity overall

26
Q

What does the initial attack in the test with bradys reagent involve?

A

A nucleophile

27
Q

What does the product of the test with bradys reagent contain

A

C=N

28
Q

What do the reagents provide in the formation of a hydroxynitrile?

A

HCN and KCN
HCN provides CN- ions and H+ ions
KCN increases the concentration of CN- ions, insufficient with HCN alone

Chemistry (personal) (15 decks)

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