All Reagents And Conditions

Question 1

Reduction of acids

Answer 1

LiAlH4 in dry ether, room temp

Question 2

Oxidation of acids + which acids can be oxidised

Answer 2

H2SO4(aq), KMnO4, heat under reflux + methanoic acid and ethanedioic acid

Question 3

Conversion of acid into acyl halide
Name all possible reactions

Answer 3

PCl5(s), room temp
PCl3(l), heat
SOCl2 in pyridine, heat

Question 4

Reaction of alcohols with reactive metals
- State product formed

Answer 4

Na, Mg. etc., room temp
- alkoxide and 1/2 H2

Question 5

What are the balanced equations for conversion of acid to acyl halide

Answer 5

RCOOH + PCl5 -> RCOCl + POCl3 + HCl

3RCOOH + PCL3 -> 3RCOCl + H3PO3

RCOOH + SOCl2 -> RCOCl + SO2 + HCl

Question 6

Esterification

Answer 6

Conc. H2SO4, heat under reflux

Question 7

Balanced equation for esterification

Answer 7

(Reversible) ROH + R’COOH -> R’COOR + H2O

Question 8

Conversion of alcohol into RX
- for each r&c write out the equation

Answer 8

1. PCl5(s), room temp
   ROH(l) + PCl5 -> RCl(l) + POCl3(l) + HCl(g)
2. PCl3(l), heat
   3ROH(l) + PCl3 -> 3RCl(l) + H3PO3(l)
3. SOCl2 in pyridine, heat
   ROH(l) + SOCl2(l) -> RCl(l)+ SO2(g) + HCl(g)

Question 9

The only reactions esters can undergo

Answer 9

Hydrolysis (acidic): HCl (aq), heat
Hydrolysis (basic): NaOH(aq), heat

Question 10

Equations for hydrolysis of esters

Answer 10

Acidic:
(Reversible) RCOOR’ + H2O -> RCOOH + R’OH

Alkaline:
RCOOR’ + NaOH -> RCOO-Na+ + R’OH

Question 11

All chemical reactions of acyl halides occur at?

Answer 11

Room temperature because acyl halides are the most reactive homologous series

Question 12

Reactions of acyl halides
- name the products

Answer 12

1. ROX + H2O -> RCOOH(carboxylic acid) + HX
2. ROX + ROH -> RCOOR’(ester) + HX
3. ROX + NH3 -> RCONH2(amide) + HX
4. ROX + RNH2 -> RCONHR’(amide) + HX

Question 13

Reactions of acid anhydrides
- name the products

Answer 13

RCOOCOR’ + H2O -> RCOOH + RCOOH
RCOOCOR’ + ROH -> RCOOH + RCOOR’

Question 14

Halogenation of arenes

Answer 14

Anhydrous AlX3/FeX3, room temp
Al/Fe, X2, room temp

Question 15

Oxidation of alcohols
- give products

Answer 15

H2SO4(aq), KMnO4/K2Cr2O7, heat under reflux
- primary alcohol produces aldehyde (further oxidises into carboxylic acid)
- secondary alcohol produces ketone
- tertiary alcohol CANNOT be oxidised

Question 16

Nitration of arenes

Answer 16

Conc. HNO3, conc. H2SO4, maintained at 55 degrees Celcius

Question 17

Friedel-Crafts Alkylation

Answer 17

Arenes
Anhydrous AlX3/FeX3, RX(alkyl grp), room temp

Question 18

Friedel-Crafts Acylation

Answer 18

Arenes
Anhydrous AlX3/FeX3, RCOX(acyl grp), room temp

Question 19

Nitration of alkylbenzenes vs nitration of benzenes

Answer 19

30 degrees Celcius vs 55 degrees Celcius

Question 20

Free-radical substitution

Answer 20

Limited X2(g), UV light

Question 21

Side-chain Oxidation of arenes
- give the products

Answer 21

H2SO4(aq), KMnO4, heat under reflux
- methylbenzene gives benzoic acid
- propylbenzene gives benzoic acid and ethanoic acid
- ethylbenzene gives benzoic acid, methanoic acid which further oxidises to give CO2 + H2O

Question 22

Normal oxidation of aldehydes

Answer 22

H2SO4(aq), KMnO4/K2Cr2O7, heat under reflux

Question 23

Milder oxidation of aldehydes
- give the products

Answer 23

Fehling’s Solution, heat
- carboxylate + Cu2O + H2O

Question 24

Tollen’s reagent
- what is the overall equation

Answer 24

RCOH + 2Ag+ + 3OH- -> RCOO- + 2Ag + 2H2O

Question 25

Reaction with 2,4-DNPH Draw and name DNPH

Answer 25

2,4-DNPH, room temp

Question 26

Reaction with HCN - what type of reaction is it

Answer 26

Cold HCN(aq), trace amts. of KCN(aq) - step-up reaction

Question 27

Reduction of carbonyl compounds - state products formed

Answer 27

LiAlH4 in dry ether, room temp NaBH4 in methanol, room temp H2(g), Ni(s) catalyst, heat - ketone forms secondary alcohol, aldehyde forms primary alcohol

Question 29

Iodoform for carbonyl compounds - state products and why - write out balanced eqn

Answer 29

I2(aq), NaOH(aq), heat - carboxylate because acid formed reacts with NaOH due to acid-based rxn, CHI3, NaI, H2O (2 in 1 rxn: oxidation and acid-base) carbonyl + 3I2 + 4NaOH -> carboxylate + CHI3 + 3NaI + 3H2O

Question 30

Triiodoomethane test - state type of reaction and give products

Answer 30

I2(aq), NaOH(aq), heat - iodoform and a step-down rxn - carboxylate and CHI3

Question 31

Dehydration of alcohols

Answer 31

Excess conc. H2SO4, 170 degrees Celsius Al2O3, heat

Question 32

Esterification of alcohols

Answer 32

Conc. H2SO4, heat under reflux

Question 33

Acylation of alcohols - state products

Answer 33

@ room temp R’COX + ROH -> R’COOR + HX - ester and hydrogen halide

Question 34

Reaction of phenols with reactive metals

Answer 34

Na/Mg etc., room temp

Question 35

Acylation of phenols

Answer 35

@room temp

Question 36

Reaction of phenols with neutral FeCl3(aq)

Answer 36

Neutral FeCl3(aq), room temp

Question 37

Halogenation of phenols - state both types and what direction it would be

Answer 37

Mono-sub X2(non-aq), room temp (2 or 4-directing) Tri-sub X2(aq), room temp (2,4,6-directing)

Question 38

Nitration of phenols - state both types and what direction it would be

Answer 38

Mono-sub Dilute HNO3, room temp Tri-sub Conc. HNO3, room temp

Question 39

Hydrolysis of haloalkanes

Answer 39

NaOH(aq), heat under reflux - could also be other Gp 1 hydroxides

Question 40

Reaction of haloalkanes with NaCN - state type of reaction

Answer 40

Ethanolic NaCN, heat under reflux

Question 41

Reduction of nitriles

Answer 41

H2(g), Ni(s) catalyst, heat LiAlH4 in dry ether, room temp

Question 42

Hydrolysis of nitriles

Answer 42

Acidic: HCl(aq), heat Alkaline: NaOH(aq), heat

Question 43

Ammonolysis of haloalkanes - state product formed

Answer 43

Excess conc. ethanoic NH3, heat in sealed tube - amine + HX

Question 44

Dehydrohalogenation

Answer 44

Ethanolic NaOH/KOH, heat under reflux