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CHAPTER 1

Learning Activities 1

Worksheet 1

This worksheet is about identifying the special nature of the benzene hydrocarbon.

Complete this graphic organiser of ideas:

1.

2.

3.

Similarities

BENZENE CYCLOHEXENE

Differences

With regards to

1.

2.

3.

4.

Worksheet 2 The bond length betweencarbon-carbon bonds in

benzene is greater than a

single carbon-carbon or

double carbon-carbon

bond.



This worksheet is all about the bonding in benzene.

Colin

Ann

Yanlan

Shaun

Mary

Dave

Wenli Imran

Only TWO of these statements are completely correct. Which are these? Correct the

other six statements by altering a key word.

Worksheet 3

The bond angle

between the

carbon atoms in a

benzene ring is

90o

Each carbon

atom in a

benzene ring

has four

molecular

orbitals.

Bonds between

carbon and

hydrogen atoms

in benzene are л

molecular bonds.

Overlap of s

and p orbitals

create the л

bonds in a

benzene

molecule.

Benzene is an unsaturated molecule

and therefore prefers to undergo

addition reactions rather than

substitution reactions.

The benzene molecule is a

perfect hexagon shape and is

more stable than expected.

Above and below

the carbon ring are

σ orbitals for

the delocalised

electrons.



This worksheet is about electrophilic substitutions reactions of benzene.

1. Consider the bromination of benzene.

(a) Complete the overall equation for bromination.

C6H6 + Br 2 → ……… + ………..

(b) What is the halogen carrier in this reaction?

(c) (i) What is the electrophile in this particular reaction?

(ii) Why does this electrophile attack the benzene ring?

(d) Show the mechanism of this reaction with the help of curly arrows.

2. Consider the nitration of benzene.

(a) Complete this equation for the formation of the electrophile.

HNO3 + 2H2SO4 → …………+ ……….. + ………….

(b) Draw the structure of di-substituted and tri-substituted products from the

nitration of benzene.

3. Consider the alkylation of benzene by the Friedal-Craft reaction.

(a) Complete the overall equation.

C6H6 + C2H5Cl → ……….. + …………

(b) (i) What is the catalyst in this substitution?

(ii) What is the electrophile?

(iii) Write an equation to show the formation of this electrophile.

Worksheet 4



This worksheet aims at testing your knowledge about nomenclature and structural

formula of arenes and substituted phenols.

Match the correct name to the correct formula by drawing a line between the two.

Name Structural Formula

COOH

4-nitrophenol

OH

phenylmethanol OH

OH

NO2

2-chlorophenol

OH

CH3

3-hydroxybenzoic acid

Cl

Cl

benzene-1,2-diol OH

CH2OH

2-chloro-methylbenzene

Worksheet 5

This worksheet aims at testing your knowledge of the important chemical reactions of phenol.



Give the structural formula(e) and name(s) of the organic product(s) formed by the

following reactions.

Structural Formula Name

Na or

NaOH

CH3Cl

AlCl3

OH

dilute

HNO3

Br 2

N= N

Worksheet 6

This worksheet aims at comparing aromatic alcohols with aliphatic alcohols.

Complete the table to show the comparison.



Comparison Phenol Ethanol (Aromatic) (Aliphatic)

1. pH neutral

2. Reaction with no reaction

neutral iron (III)

chloride solution

3. Oxidation with no reaction

acidified potassium

dichromate (VI)


dilute sodium

hydroxide solution

5. Reaction with few bubbles of

sodium metal hydrogen gas


sodium hydrogen

carbonate


bromine in dark


carboxylic acid

Worksheet 7

Try this spiral crossword as a ‘fun’ way of consolidating knowledge about phenols.

Answer each of the following clues by starting in the square marked 1 at the centre of

the grid and writing your answer in a clockwise spiral. The last letter of each answer

is the first letter of the next. Follow the direction shown by the arrows and do not let

any word cross the bold lines. To help the number of letters for each answer is given

in brackets.



1. The colour neutral iron (III) chloride goes when phenol is added. (6)

2. The number of different elements in a phenol molecule. (5)

3. The reaction of phenol with an acid chloride is an example of this type of chemical

reaction. (14)

4. The phenoxide ion is an example of this type of organic species. (11)

5. This type of substitution takes place on the benzene ring with phenol and bromine.

6. An old chemical name for phenol.

7. This element is responsible for phenol burning with a sooty flame. (6)

8. This phenol derivative is formed when phenol is reacted with dilute nitric acid. (11)

9. This indicator can be used to show the acidic nature of phenol. (6)

10. Physical state of phenol at room temperature. (5)

11. Describes how the negative charge of the phenoxide ion is stabilised by the benzene ring. (14)

12. The name of the catalyst used when adding hydrogen to the benzene ring of

phenol. (6)

13. At 41ºC phenol changes to this. (6)



CHAPTER 2


Worksheet 1

This worksheet is all about carbonyl compounds.

(A) CH3-CH2-CHO (B) H-CHO (C) CH3-CH2-CO-CH2-CH3

(D) CH3-CH2-CH2-COOH (E) CH3-CO-CH3 (F) C6H5-CHO

1. Name all of these carbonyl compounds.

2. Which two are structural isomers?

3. Which ones would produce a silver mirror with Tollen’s reagent?

4. Which would not produce a precipitate with 2,4-dinitro-phenylhydrazine (Brady’s

reagent)?

5. Which would fizz when added to a carbonate?

6. Which would burn with the sootiest flame?

7. Which is an aromatic compound?

8. Which would be reduced to

(i) propan-1-ol ? (ii) propan-2-ol?

(iii) benzyl alcohol? (iv) methanol?

9. Which would be oxidised to

(i) propanoic acid? (ii) benzoic acid?

(iii) methanoic acid?

10. Give the mechanism for the nucleophilic addition reaction of hydrogen cyanide to

compound A.



Worksheet 2

This worksheet is all about oxidation and reduction of carbonyl compounds. Complete

the table below by drawing the structure and naming the organic product fromreduction or oxidation of the named carbonyl compound. If there is no reaction then

say so.

Oxidation Reduction

Structure Name Structure

Name

propanal

butan-2-one

methanal

propanone

pentan-3-one

ethanal



CHAPTER 3


Worksheet 1

This worksheet is to improve your IT skills. The table shows the boiling points of the

first six carboxylic acids in the homologous series with a general formula

CnH2n+1COOH.

value of n name of

carboxylic acid

boiling pointo/C

molecular

formula

relative

molecular

mass

1 methanoic 101

2 ethanoic 118

3 propanoic 141

4 butanoic 164

5 pentanoic 186

6 hexanoic

1. Complete the table by calculating the relative molecular mass of the carboxylic

acid [Ar (C) = 12, Ar (H) = 1, Ar (O) = 16]

2. Using a spreadsheet program arrange your data as shown below:

A B C D E F

1 relative molecular mass

2 101 118 141 164 186

3. Using the chart options draw a line graph of boiling point (y-axis) against relative

molecular mass (x-axis). Label it ‘Boiling Point Graph’. Preview the chart before you

print it. Try other types of charts and choose the most effective one.

4. Use your graph to predict the boiling point of hexanoic acid.



Worksheet 2

This worksheet is all about the formation of esters. Compete the table by naming theester and/or identifying the original alcohol and carboxylic acid it was made from.

Ester Alcohol Carboxylic Acid

CH3COOC2H5

……name……

CH3OH C2H5COOH

HCOOC3H7

….name……

C4H9OH CH3CH2CH2COOH

C3H7COOC3H7….name…..



Worksheet 3

This multiple choice worksheet is to test your knowledge of carboxylic acids. Select

either A, B, C or D. Only one of the answers is completely correct.

1. Which one of the following substances would be oxidised to 2-methylpropanoic

acid?

A. (CH3)2CHCH2OH B. CH3CH2CHOHCH3

C. CH3CH2CH2CH2OH D. (CH3)3COH

2. Which is the best description of the reaction between C3H7OH and HCOOH?

A. addition B. hydrolysis

C. esterification D. elimination

3. When phenylethanoate is hydrolysed by excess aqueous sodium hydroxide, the

products of the reaction are

A. phenol and ethanoic acid B. phenoxide ions and ethanoate ions

C. ethanol and benzoic acid D. phenol and ethanoate ions

4. Which of these organic compounds would bubble when magnesium is added?

A. CH3CHO B. HCOOH

C. CH3COCH3 D. HCHO

5. Which one of the following compounds would react with the product of its own

oxidation product to form a sweet smelling liquid?

A. propanal B. propanone

C. propan-1-ol D. propan-2-ol



6. Which of these acids is the strongest?

A. CH3COOH B. ClCH2COOH

C. Cl2CHCOOH D. Cl3CCOOH

Questions 7 to 12 refer to the four carboxylic acids A, B, C and D listed below.

A. ethanoic acid

B. ethanedioic acid

C. butanoic acid

D. benzoic acid

7. Which of these acids is least soluble in cold water?

8. Which of these acids will decolourise a warm acidified solution of potassium

manganate (VII)?

9. Which of these acids has the lowest boiling point?

10. Which acid can form two sodium salts?

11. Which of these acids is found in rhubarb and is called oxalic acid?

12. Which of these acids when concentrated is called ‘glacial’ as in cold weather it

crystallises?

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