"Mind-map Style" revision

Question 1

Complete the image below to show the decarboxylation of a carboxylic acid (In this case Ethanoic acid).

Answer 1

This reaction produces a hydrocarbon with one less Carbon atom than the acid.

This reaction is useful for structure determination since the hydrocarbon can be easily identified (by boiling point) once the Carboxyl group has been removed.

Question 2

Complete the equation below show the photo-chlorination of methane.

Answer 2

Question 3

Complete the equation below to give the reagents, conditions and products of the reaction of an alkene (in this case Propene) with Br_(aq).

Answer 3

This reaction produces a Bromo alcohol.

Question 4

Complete the equation below to give the reagents, conditions and products of the oxidation of an alkene (in this case Propene).

Answer 4

Question 5

Complete the equation below to give the reagents, conditions and products of the Hydrodgenation of an alkene (in this case Propene).

Answer 5

This reaction is used commercially to Hydrogenate Heavily unsaturated Oils to produce Margarines.

Question 6

Complete the equation below to give the reagents, conditions and products of the reaction of an alkene (in this case Propene) with Br_(l).

Answer 6

Question 7

Complete the equation below to give the reagents, conditions and products of the reaction of an alkene (in this case Propene) with HBr. (Both gaseous and aqueous).

Answer 7

This reaction follows Markovnikov’s rule. The Hydrogen of the HBr attatches to the carbon with the greatest number of Hydrogen atoms already attached.

Question 8

Complete the equation below to give the reagents, conditions and products of the first step in the reaction of an alkene (in this case Propene) with concentrated H₂SO_4.

Answer 8

Question 9

Complete the equation below to give the reagents, conditions and products of the second step of the reaction of an alkene (in this case Propene) with Concentrated H₂SO₄.

Answer 9

Question 10

Complete the equation below to give the reagents and conditions of the Production of an alkene (in this case Propene) From propan-1-ol.

Answer 10

Question 11

Complete the equation below to give the reagents and conditions of the Production of an alkene (in this case Propene) From propan-1-ol using H₂SO_4.

Answer 11

Question 12

Complete the equation below to give the reagents and conditions of the Production of an alkene (in this case Propene) from a halogeno alkane.

Answer 12

Question 13

Complete the equation below to give the reagents, conditions and products from the nitration of Benzene.

Answer 13

The Nitronium ion is created in solution by Reacting Concentrated HNO₃ and conc H₂SO_4. If the temprature rises above 55^oC dinitrobenzene is formed.

Question 14

Complete the equation below to give the reagents, conditions and products for the first stage of the conversion of Benzene to Phenol.

Answer 14

Question 15

Complete the equation below to give the reagents, conditions and products for the second stage of the conversion of Benzene to Phenol.

Answer 15

Question 16

Complete the equation below to give the reagents, conditions and products Required for the production of Chlorobenzene.

Answer 16

This is another example of electrophillic substitution.

Happens only with Chlorine or Bromine.

A halogen carrier is a fidel-crafts catylist such as Aluminium chloride (AlCl₃).

Question 17

Complete the equation below to give the reagents, conditions and products when ethanoyl chloride reacts with Benzene.

Answer 17

A halogen carrier is a fidel-crafts catylist such as Aluminium chloride (AlCl3​).

Question 18

Complete the equation below to give the reagents, conditions and products for the fidel-crafts alkylation of benzene.

Answer 18

A halogen carrier is a fidel-crafts catylist such as Aluminium chloride (AlCl3​).

Question 19

Complete the equation below to give the reagents, conditions and products for the oxidation of Methyl (or other Alkyl) Benzene.

Answer 19

In this reaction the Potassium Salt of the Acid (COOK) is first obtained and then is acidified to give the free acid.

Question 20

Complete the equation below to give the reagents, conditions and products for the Chlorination of Methyl (or other Alkyl) Benzene.

Answer 20

Question 21

Complete the equation below to give the reagents, conditions and products for the chlorination of the Methyl (or other Alkyl) side chain of an alkyl Benzene.

Answer 21

Question 22

Complete the equation below to give the reagents, conditions and products for the Hydrogentation of Benzene.

Answer 22

Question 23

Complete the equation below to give the reagents, conditions and products for the Photo Chlorination of Benzene.

Answer 23

this process takes longer with Benzene than it does with Alkenes because of the Pi system of delocalised electrons.

Question 24

Complete the equation below to give the reagents, conditions and products for the production of a Chloro Alkane (in this case ChloroEthane) From an Alkene.

Answer 24

N.B the degree of halogenation depends on the length of exposure.

Question 25

Complete the equation below to give the reagents, conditions and products for the production of a Halogeno Alkene from an alcohol. (in this case ChloroEthane)

Answer 25

Question 26

Complete the equation below to give the reagents, conditions and products for the Dehalogenation of Chloroethane.

Answer 26

Question 27

Complete the equation below to give the reagents, conditions and products for The alkaline Hydrolysis of a Halogeno Alkane.

Answer 27

This is a nucleophillic substitution reaction. Chloro Ethane is much more reactive than Chlorobenzene so with Chlorobenzene Hydrolysis takes much longer. This is because the electrons of the Chlorine atom not used in bonding beome part of the delocalizes rings of electrons above and below the plane of the ring. This makes benzene very resistant to attack by nucleophiles.

Question 28

Complete the equation below to give the reagents, conditions and products for the Silver Nitrate Test for a halogeno Alkane (In this case Chloroethane).

Answer 28

This reaction (With a chloroalkane) produces a white precipitate which is soluble in dil ammonia. With a Bromoalkane a pale cream precipitate is given which is soluble in conc ammonia. With Iodine a pale yellow precipitate is given which is insoluble in conc ammonia.

Question 29

Complete the equation below to give the reagents, conditions and products for the amination of a halogeno alkane.

Answer 29

Aliphatic amines are produced through this process. The two reactants are dissolved in ethanol and are heated together in a bomb. (a metal container which will withstand a high pressure). The first product is the ammonium salt (RNH₃⁺ X^-). To extract the free amine an alkali is added and then fractional distillation is used.

Question 30

Complete the equation below to give the reagents, conditions and products for the production of a nitrile compound from a hlogeno alkane (in this case Chloroethane).

Answer 30

When heated with KCN dissolved in either ether or Propanone Chloroethane is converted to Nitrile propane. This is therefore an effective means of increasing the length of a Carbon chain.

Question 31

Complete the equation below to give the reagents, conditions and products for the production of an alcohol (in this case ethanol) from an alkane.

Answer 31

Question 32

Complete the equation below to give the reagents, conditions and products for the production of an alcohol (in this case ethanol) through the Hydrolysis of a halogenoalkane.

Answer 32

This is a Nucleophillic substitution/Hydrolysis reaction

Question 33

Complete the equation below to give the reagents, conditions and products for the production of an alcohol (in this case Ethanol) through reduction of a carbonyl compound.

Answer 33

When this reaction is performed on an aldehyde a primary aliphatic alcohol is formed. When it is performed on a Keytone an aliphatic secondary alcohol is formed. NaBH₄ in water Will reduce aldehydes and keytones however a stronger reducing agent (LiAlH₄ in Dry ether) is needed for Carboxylic acids.

Question 34

Complete the equation below to give the reagents, conditions and products for the Dehydration (elimination) of an alcohol (in this case Ethanol)

Answer 34

Cold sulfuric acid reacts with an alcohol to produce an alkyl Hydrogen Sulfate (CH3CH2OHSO3).heating the product with excess sulfuric acid gives an alkene by losing the elements of water.

Question 35

Complete the equation below to give the reagents, conditions and products for the esterification of an alcohol (in this case ethanol).

Answer 35

Esters are sweet smelling The yeild of this reaction is small as it reaches equilibrium. The product is distilled from the reaction mixture.

Question 36

Complete the equation below to give the reagents, conditions and products for the esterification using ethanoyl chloride of an alcohol (in this case ethanol).

Answer 36

This reaction produces a better yeild.

Question 37

Complete the equation below to give the reagents and conditions required to convert an alcohol (in this case Ethanol) into a halogeno alkane (in this case bromoethane).

Answer 37

This is a dehydration reaction as it produces water as a waste product. The HBr is made in situe by heating NaBr with Conc Sulfuric acid.

Question 38

Complete the equation below to give the reagents, conditions and products for the Oxidation of an alcohol (in this case ethanol.)

Answer 38

Primary alcohols produce Aldehydes and then Carboxylic acids Secondary alcohols produce Keytones Tertiary alcohols do not undergo oxidation. This can therefore be used to tell the difference between various classes of alcohols

Question 39

Complete the equation below to give the reagents, conditions and products for the Conversion of Phenol into Sodium Phenoxide.

Answer 39

Sodium Phenoxide Will then react readily with Acyl Chlorides to give an ester.

Question 40

Complete the equation below to give the reagents, conditions and products for the reaction of phenol with Bromine water.

Answer 40

This Produces a molecule similar to TCP - 2,4,6-tribromophenol. This reaction results in The productioon of a white solid and hence decolorises Bromine water in an electrophillic substitution reaction. Phenol is more readily attacked by electrophiles because the lone pair of electrons on the OH and O^- groups and the ring increase the avalibility of electrons in the ring,

Question 41

Complete the equation below to give the reagents and conditions for the conversion of Phenol to an aromatic keytone. (in this case Phenyl Methyl Ketone)

Answer 41

Question 42

Complete the equation below to give the reagents and conditions for the Production of an Acid chloride (in this case Ethanoyl Chloride) From a Carboxylic acid.

Answer 42

This reaction produces POCl₃ and HCl as waste products.

Question 43

Complete the equation below to give the reagents and conditions for the Production of a carboxylic acid (in this case ethanoic acid) from a nitrile compound.

Answer 43

Question 44

Complete the equation below to give the reagents, and conditions necesarry for the formation of a carboxylic acid (in this case ethanoic acid) from a Primary alcohol/aldehyde.

Answer 44

Sulfuric acid is used to acidify the reaction mixture and the required product can be distilled from the mixture after heating under reflux.

Question 45

Complete the equation below to give the reagents, conditions and products for the esterification of a carboxylic acid (in this case ethanoic acid).

Answer 45

This reaction takes place with Concentrated Sulfuric acid acting as a catylist and a dehydrating agent, removing water and pushing equilibrium to the right.

Question 46

Complete the equation below to give the products for the reaction of a carboxylic acid (in this case ethanoic acid) with Sodium compounds.

Answer 46

If NaOH is used and the reaction mixture is heated then Decarboxylation will occur.

Question 47

Complete the equation below to give the reagents, conditions and products for the decarboxylation of a carboxylic acid (in this case ethanoic acid).

Answer 47

In this reaction a Hydrocarbon is formed which has one less Carbon atom than the acid. This reaction is widely used in structure determination since the Hydrocarbon is easily identified once the Carboxyl group has been removed.

Question 48

Complete the equation below to give the reagents, conditions and products for the Reduction of a Carboxylic acid (In this case ethanoic acid).

Answer 48

Question 49

Complete the equation below to give the reagents, conditions and products for the reaction of an aldehyde with Tollen's reagent/Fehling's Solution.

Answer 49

An aldehyde treated with Tollen's reagent and heated in a water bath will produce a silver mirror which will coat the inside of the test tube. When an aldehyde is heated to boiling point with Fehling's solution/Benadicts reagent a Brick red precipitate of Copper-1-Oxide forms.

Question 50

Complete the equation below to give the reagents, conditions and products for the Oxidation of an aldehyde.

Answer 50

Question 51

Complete the equation below to give the products for reaction of an aldehyde with Brady's reagent.

Answer 51

The 2,4-dinitro-phenyl-hydrazones formed through this process are Orange or Yellow solids and are easily crystalised and purified. Demonstration of the melting point can be used to identify the original aldehyde or keytone.

Question 52

Complete the equation below to give the reagents, conditions and products for the reduction of an aldehyde.

Answer 52

This produces a primary alcohol.

Question 53

Complete the equation below to give the reagents, conditions and products for the iodoform test on an Aldehyde.

Answer 53

Iodoform (CH₃) - a pale yellow solid is formed when a suitible carbonyl compound is warmed with NaOH and Iodine. In order for the test to be positive the Carbonyl group must be next to a methyl group. hence why it is only positive for Ethanal.

Question 54

Complete the equation below to give the reagents and conditions for the production of an aldehyde from a Primary alcohol (in this case ethanol).

Answer 54

Question 55

Complete the equation below to give the reagents, conditions and products for the Oxidation of an alcohol (in this case ethanol.) using Cr₂O₇^2-

Answer 55

Question 56

Complete the equation below to give the conditions and products for the reaction of a keytone with Tollens Reagent/Fheling's solution.

Answer 56

Keytones do not produce a silver mirror or brick red precipitate with Tollens reagent or Fhelings solution respectively.

Question 57

Complete the equation below to give the products for the reaction of a keytone with Brady's reagent.

Answer 57

Question 58

Complete the equation below to give the products and result produced from a keytone in the Iodoform test.

Answer 58

Question 59

Complete the equation below to give the reduction of a keytone.

Answer 59

This produces a secondary alcohol.

Question 60

Complete the equation below to show the production of a Keytone from a secondary alcohol.

Answer 60

Question 61

Complete the equation below to show the production of a Nitrile compound from an amide.

Answer 61

Question 62

Complete the equation below to give the production of a nitrile compound from the ammonium salt of an acid.

Answer 62

This reaction requires heat.

Question 63

Complete the equation to give show the production of a nitrile from a halogeno compound.

Answer 63

This occurs when a halogeno alkane is heated with Potassium Cyanide dissolved in either ether or propanone. It is a way of increasing the number of carbon atoms in a chain.

Question 64

Complete the equation below to give the production of a carboxylic acid from a nitrile.

Answer 64

Question 65

Complete the equation below to give the reduction of a nitrile.

Answer 65

In this reaction the reducing agent must not be acidic as it would cause hydrolysis of the nitrile

Question 66

Complete the equation below to show the production of a primary aliphatic amine from a halogeno alkane.

Answer 66

In this reaction the two reactants are dissolved in ethanol and then heated together in a bomb. To extract the free amine an alkali is added and then fractional distilation is used. i.e: RX + NH₃ = RNH₃⁺ X^- RNH3+ X- + NaOH = CH₃NH₂ + NaX + H₂O

Question 67

complete the equation be low to give the production of a primary aliphatic amine from a nitrile compound.

Answer 67

Question 68

Complete the equation below to show the Acylation (in this case ethanoylation) of a primary aliphatic amine.

Answer 68

These substituted amides are solids and so can be used to identify the original amine. Ethanoic anyhydride reacts in the same way.

Question 69

Complete the equation below to give the reaction of a primary aliphatic amine with Nitrous acid.

Answer 69

Amines undergo different reactions with nitrous acid. The nitrous acid is produced in situe (as it is unstable) ny reacting Nitrite (NO₂) with hydrochloric acid at 5⁰C. The first reaction forms a diazonium ion: R-NH₂ = R-N⁺≡N-Cl^- . Diazonium ions of _primary aliphatic amines_ decompose giving of nitrogen gas: R-N+≡N-Cl- + H₂O = ROH + N₂ + HCl.

Question 70

Complete the equation below to give the production of an aromatic amine from nitronenzene. (in this case phenylamine/aniline)

Answer 70

This is a redox reaction with HCl acting as a reducing agent. The mixture is refluxed for about 30 minutes and then NaOH is added to release the aniline which is extracted by steam distillation. A mixture of water and aniline collects and ether is used to extract the aniline. The ether is distilled off and the aniline further purified by boiling under reduced pressure, It decomposes at it's normal boiling point.

Question 71

Complete the equation below to show the acylation of an aromatic amine. (in this case aniline).

Answer 71

Question 72

Complete the equation below to give the reaction of phenylamine (aniline ) with nitrous acid.

Answer 72

Amines undergo different reactions with nitrous acid. The nitrous acid is produced in situe (as it is unstable) ny reacting Nitrite (NO2) with hydrochloric acid at 50C. This produces an aromatic diazonium compound. Unlike aliphatic diazonium compounds aromatic amines are stable in solution below 10^oC

Question 73

Complete the equation below to give the reaction between an aromatic diazonium compound and water.

Answer 73

Question 74

Complete the equation below to give the reaction between an aromatic diazonium compound and a phenol (in this case 2-napthol)

Answer 74

With phenols a coupling reaction occurs and an azo dye is produced. Above 10^oC diazo compounds decompose. With aromatic amines a coupling reaction occurs so that the two rings are joined by a -N=N- bond.

Question 75

Complete the equation below to give the production of an ester using a carboxylic acid.

Answer 75

This is a condensation reaction. The sulfuric acid acts as a catylist and dehydrating agent, removing water and shifting the equilibrium over to the right.

Question 76

Complete the equation below to give the production of an ester using a acyl chloride.

Answer 76

Question 77

Complete the equation below to give the reduction of an ester.

Answer 77

Question 78

Complete the equation below to give the hydrolysis of an ester.

Answer 78

labelling experements show that the C-O bond (in bold) in the -C**-**O-R- group is broken. The reaction is catylised by acids and alkalis. If a base is used then the first product is the salt of the base.The two products (salt and alcohol) can be easily separated. To obtain the acid from the salt it is treated with a mineral acid (e.g sulfuric acid).