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2-methylpentane
2ethyl-2-methylpropane
2,3-dimethylbutane
A. I only
B. I and II only
A. 1-chloropropene
B. 1-chlorobutane
C. 1-bromopropane
D. 1,1-dichloropropane
B. CH3CH2N(CH3)2
C. H2NCH2CO2H
D. CH3CONH2
A. CH3CH2NH2
B. CH3CONH2
C. -[CH2CONHCH2CO]n_
D. CH3CH2C ≡ N
A. 2
B. 3
C. 4
D. 5
7. How many different isomers have the formula C4H10 ?
A. 1
B. 2
C. 3
D. 4
8.
(b) (i) State and explain the trend in the boiling points of the first five alkanes. [2]
Increases Increase in mass leads to greater Van De Waal forces
(ii) Give the structural formulas for the isomers of molecular formula C4 H10 and state the
name of each one [2]
CH3CH2CH2CH3 = Butane
(ii) Draw the four structures of alcohols of formula C 4H9OH. Name each one and
label them as either primary, secondary or tertiary alcohols. [4]
(iii) Many organic compounds can exist as isomers. Draw and name an isomer of ethanoic [2]
acid,
1. When the compounds below are listed in order of decreasing boiling point (highest to lowest) what is the
correct order?
A. 4,3,1,2
B. 4,3,2,1
C. 3,4,1,2
D. 2,1,3,4
A. Methane
B Propane
C. Propan-1-ol
D. Pentan-1-ol
4. Statement (S): Solubility of alcohols in water decreases with increase in Mr.
Explanation (E): The relative proportion of the hydrocarbon part in alcohol increases with increasing Mr.
5. Explain why the boiling points of ethanol and ethanoic acid are considerably higher than the
boiling point of ethanal.
[3]
Ethanol and ethanoic acid both contain H bonds
Since H is attached to electroneg O atom.
Ethanal has only dipole forces due to C=O
6. Discuss the factors which affect the boiling points of covalently bonded compounds by reference to
the following pairs of organic substances, whose boiling points are given:
1. Which statement is correct about the reaction between methane and chlorine?
A. I and II only
D. I, II and III
A. Addition
B. Condensation
C. Dehydration
D. Hydrogenation
4. Which chemical is most likely to be a starting material for a common polymer?
A. CH3CH2CH3
B. CH3CH2OH
C. CH3CHCH2
D.
5. What will be formed when CH2 = CH2 reacts with Br2 in the dark?
A. CH2Br —CH2Br
B. CH3—CHBr2
C. CH 2 =CHBr + HBr
D. CHBr = CHBr + H 2
6. (a) Describe a chemical test to distinguish between alkanes and alkenes, giving the result in each
case. [2]
Bromine water
Alkanes = stays orange….alkenes = turns clear
(b) Name the type of polymerization reaction which C3H6 undergoes and draw the structure of a section
of the polymer chain formed from three monomer molecules.
[3]
Addition polymerization
-(CH(CH3)CH2 ) --(CH(CH3)CH2 ) --(CH(CH3)CH2 ) - (2 marks)
7. Give an equation for the complete combustion of methane, CH 4. Identify two products formed by
the incomplete combustion of methane and identify one harmful effect caused by one of the products.
CH4 + 2 O2 = CO2 + 2 H2O
Carbon monoxide (poisonous/internal suffocation)
Carbon (respiratory problems/asthma/bronchitis)
[4]
8. The plastic PVC, poly(chloroethene), is made from the monomer chloroethene, C2H3C1, by a
polymerization reaction.
(ii) State the type of polymerization reaction that occurs to make poly(chloroethene) and
identify the structural feature needed in the monomer. Addition polymers [2]
C=C (unsaturated)
(iii) Draw the structure of the repeating unit of poly (chloroethene). [1]
-( CHClCH2 )-
(iv) Explain why monomers are often gases or volatile liquids, whereas polymers are solids. [2]
9. Alkanes are often described as having low reactivity, although they do react with halogens.
Non polar
(i) Explain why alkanes are unreactive. Strong C-C and C-H bonds
[2]
(ii) The first step in the reaction of propane with bromine can be represented by the equation.
Br2→ 2Br∙
State the type of species formed in this step and name the type of bond fission. [2]
Free radical
Hemolytic fission
(i) Give a chemical test to identify ethene and state what would be observed.
(ii) Give a balanced equation for the reaction to form ethanol from ethene.
(iii) State the conditions necessary for the reaction in (ii). [4]
Bromine water
Orange to clear
A. butan-1-ol
B. butan-2-ol
C. butanone
D. butanoic acid
2. What is the final product formed when ethanol, CH3CH2OH is reacted with acidified potassium dichromate(VI)?
A. ethanal
B. ethane
C. ethanoic acid
D. ethene
3. Which compound will undergo oxidation when treated with acidified potassium dichromate(VI)?
A. CH3CH2CHO
B. CH3COCH3
C. CH3COOH
D. (CH3)3COH
4. (a) Propan-1-ol, in the presence of a small amount of oxidising agent, forms compound X,
and when refluxed with an excess of oxidising agent, forms compound Y.
(i) Identify a suitable oxidising agent and state the colour change. [2]
(ii) Draw the structural formulas of both compound X and compound Y. [2]
X = CH3CH2CHO Y = CH3CH2COOH
(b) Some alcohols are oxidized by heating with acidified potassium dichromate(VI). If oxidation
does occur, identify the possible oxidation products formed by each of the alcohols below. [4]
Indicate if no oxidation occurs.
Butanone
Butan–2–ol
5. This question is concerned with compounds having the molecular formula C3H8O.
(a) Draw the full structural formulas of the three possible isomers and give the name of each. [5]
CH3CH2CH2OH = propan-1-ol
CH3CH(OH)CH3 = Propan-2-ol
(b) Predict how each of these isomers would behave when reacted with limited (i.e. not in
excess) acidified potassium dichromate(VI) solution and describe any observation that
could be made. Write the structures of any organic products formed and give their names. [6]
1. The reaction between 1-bromopropane and warm dilute sodium hydroxide solution is described as an
SN 2 nucleophilic substitution reaction.
Substitution, nucleophilic, second order
(i) Explain each of the terms in SN 2. [3]
(ii) Write an equation and a mechanism for the reaction. [5]
Correct activated complex formed Curly arrow from Br- leaving group
(iii) State the type of substitution reaction undergone by tertiary halogenoalkanes. [1]
SN1
3. Give the structural formulas of the four isomers of molecular formula C4H9Cl. State the
name of each one and classify it as primary, secondary, or tertiary.
CH3CH2CH2CH2Cl = 1-chlorobutane = primary
[8]
(b) Each of the isomers reacts with aqueous sodium hydroxide. State what class of compound is
produced by this reaction.
alcohols
[1]
(c) (i) Identify the type of isomer (primary, secondary or tertiary) which will react with
aqueous sodium hydroxide almost exclusively by an SN1 mechanism. State the
meaning of the symbols in the term SN1 mechanism.
Tertiary
Sub, nucleophilic 1st order reaction
[2]
Topic 10 Organic Chemistry 10.6
(a) State a suitable reagent for the oxidation of B to C and C to D. Explain how the oxidation
of B to C could be achieved without further oxidation to D. [3]
Acidified/H+ potassium dichromate product must be distilled off before further oxidation
(b) The conversion of A to B takes place by an SN 2 mechanism. State what is meant by the
term SN2 and describe, by using "curly arrows" to show the movement of electron pairs, the
mechanism of this conversion.
[6] nd
Sub, nucleophilic, 2 order (1 mark)
Polarity of C-Br bond Curly arrow showing C-Br bond breaking slowest step is first step
2. This question is about four compounds A, B, C and D, which can be made from ethene by
the following reactions. All four compounds are liquid at room temperature, and each
compound's molecular formula is shown.
C2H4 C2H5O C2H4O C2H5O2
A B C D
(a) Use the information above to identify each of the compounds A, B, C and D giving the
name and structural formula of each one. [8]
(b) State the type of reaction occurring when A is converted to B and state the reagent required.
Addition reagent = H2O (and a sulfuric acid catalyst)
[2]
(c) Compound A can react with bromine. Write an equation for this reaction and
name the product. State a visible change which accompanies the reaction.
[3]
CH2CH2 + Br2 = CH2BrCH2Br 1,2-dibromoethane
Orange to clear
Topic 10 Organic Chemistry 10.7
1. The alkaline hydrolysis of primary halogenoalkanes usually follows an SN 2 mechanism. For which
compound would the rate of hydrolysis be fastest?
A. CH3CH2CH2F
B. CH3CH2CH2C1
C. CH3CH2CH2Br
D. CH3CH2CH2I
A. (CH3)3CC1
B. CH3CH2CH2CH2Br
C. (CH3)3CBr
D. CH3CH2CH2CH2C1
3. What is the major product when an halogenoalkane is reacted with a large excess of
ammonia?
A. An amine
B. An amide
C. An amino acid
D. An alkene
4. Which one of the chloroalkanes below will hydrolyse most rapidly?
A. CH3CH2CH2CH2C1
A. Ethane
B. Ethanol
C. Ethylamine
D. Water
6. (i) Draw the structure of the four structural isomers of C4H9Cl. [2]
.
CH3CH2CH2CH2Cl CH3CH(Cl)CH2CH3
(ii) Identify one isomer in (iii) that undergoes a substitution reaction mainly by an SN1 [1]
mechanism.
Tertiary one
(iii) Write the mechanism for the reaction that occurs when the isomer identified in (ii) is [3]
warmed with aqueous sodium hydroxide. Use curly arrows to present the movement of
electron pairs.
Polarity of C-Br bond Curly arrow showing C-Br bond breaking slowest step is first step
7. (a) (i) Draw the structures of 2-chloropropanoic acid and 2-hydroxypropanoic acid. [2]
CH3CH(Cl)COOH CH3CH(OH)COOH
(b) Deduce how the rate of reaction of CH2CH2CH2Br with NaOH would compare with that of the
compound CH2CH2CH2Cl with NaOH. Explain your answer by referring to the Data Booklet.
Bromo is faster
Data booklet shows that strength of C-Br bond is weaker (since less polar) and so can be broken [2]
more easily.
Topic 10 Organic Chemistry 10.8
A. Butyl methanoate
B. Methyl butanoate
C. Methyl propanoate
D. Pentanone
2.
A. addition.
B. esterification.
C. hydrolysis.
D. neutralisation.
What will be the final product if aminoethane (ethylamine) is used instead of NH3 ?
A. CH3CONHCH2CH3
B. CH3CONHCH3
C. CH3CONH 2
D. CH3CONH2CH2CH3
5. When ethanol is warmed with ethanoic acid in the presence of an acid catalyst a new
product is formed.
(a) Write the balanced equation for the reaction that takes place using the structural
formulas of the organic reactants and products. [3]
CH3CH2OH + CH3COOH CH3COOCH2CH3 + H2O
(b) State how the organic product may be distinguished from the reactants and to which
homologous series it belongs. [2]
Ester has low bp/volatile…has strong smell.
(c) State two reasons why concentrated sulfuric acid is used. [2]
(d) State and explain how the solubility of the product in water compares with the
solubililty of the two reactants in water. [2]
Less soluble
Esters have no H bonding
6. (i) Draw the structural formula of methyl methanoate. State the conditions and the starting
materials for the preparation of methyl methanoate in the laboratory. Write a balanced
chemical equation for the reaction.5]
HCOOCH3
materials = methanol and methanoic acid
Conditions = heat + acid (sulfuric) catalyst
CH3OH + HCOOH HCOOCH3 + H2O
(ii) Draw the structural formula of an isomer of methyl methanoate. State two physical
properties and one chemical property that would be different for the two compounds.
State how each of these properties differ for the two compounds.
Isomer = CH3COOH
Physical = solubility in water/boiling point/volatility
Esters cannot H bond but carboxylic acids can
Chemical = Acidity
Carboxylic acids will react with carbonates/metals….esters won t.
[5]
7. Hexanedioic acid and 1,6-diaminohexane react together to form a synthetic polymer.
There are many natural polymers, some of the most familiar being proteins formed from 2-
amino acids.
(i) Give the structural formula of each monomer in the synthetic polymer. [2]
NH2(CH3)6NH2 HOOC (CH3)4 COOH
(ii) State the type of polymerization reaction that occurs between these two monomers
and identify the structural feature needed in the monomers. [2]
(iii) Draw the structure of and state the type of linkage formed in this polymer, and
identify the other product of this polymerization reaction. [3]
Amide link (-C=O – NH -) other product = water
8. (a) Given the structures of the repeating units of the polymers below, identify the monomers
from which they are formed.
[4]
CH2=CH2
-( CH2-CH2 )- HOOC-CH(CH3)-NH2
-( CO-CH(CH3) NH )-
NH2(CH3)6NH2 and HOOC (CH3)4 COOH
-( NH-(CH2)6-CO-NH-(CH2)4-CO )- (2 marks)
(b) Describe the essential differences between the structures of monomers that form addition [2]
polymers and the structures of monomers that form condensation polymers.
Stereoisomerism HL ONLY
A. NH2CH2COOH
B. CH3CH(NH2)COOH
C. CH3C(NH2)2COOH
D. (CH3)2C(NH2)COOH
A. CH3COCH(CH3)2
B. (CH3)3CCHO
C. CH3CH2COCH2CH3
D. CH3CH2CH(CH3)CHO
A. CH3CH2CH2CH2NH2
B. CH3CH2CHCH3
NH
C. CH3CH2NCH2CH3
D. CH 3 CH2 NCH3
CH3
4. W has the structure
CH3 H
(i) Give the structure of the geometrical isomer of W. C=C
H CH2CH3
(ii) Explain why W has a geometrical isomer.
No rotation of C=C bond
(iii) Draw two structures for CH3CH2CH(Cl)CH3, showing the relationship between them.
[2]
5. There are geometrical isomers of the cyclic compound C4H6Cl2 Draw the structural
formula of two isomers and explain why these two isomers exist.
3 D drawing of cis and trans cyclic isomers
[2]
6. (a) Consider the following compounds:
(i) Identify the compound which exhibits optical isomerism and draw the structures of
the two isomers.
2-chloropentane
[3]
(ii) Describe how these two isomers can be distinguished experimentally.
(b) There are four isomers with the formula C5 H10 which contain a three-membered carbon
ring. Draw these isomers and label them A, B, C and D.
[2]
(ii) Indicate, by writing two letters (chosen from A, B, C and D) a pair of isomers that are
structural isomers and a pair that are geometrical isomers. [2]
Chain isomers 2 x CH3 on same C’s..or CH3CH2 (2 marks)
Structural isomers:
Geometrical isomers: Cis and trans isomers …2 x CH3 groups on different C’s….(2 marks)
(iii) From the four isomers A, B, C and D, draw the structure of an isomer that shows
optical isomerism and mark the chiral centre with an asterisk (*). [1]
Either of the geometric isomers
(c) Use the examples from parts (a) and (b) to explain the existence of geometrical isomers. [1]
Restricted rotation of a ring structure
8. (a) Explain the term plane-polarized light and describe how the optical isomers of
CH3CH2CHClCH3 could be distinguished using a polarimeter.
Light vibrating in one plane One isomer rotates it to left, other to right
[2]
(b) Explain why a sample of CH3CH2CHClCH3 produced did not show optical activity.
Racemic mixture
[1]
(c) 2-chloropropanoic acid and 2-hydroxypropanoic acid can both show optical activity.
Identify the feature which both molecules possess that accounts for this property.
When 2-hydroxypropanoic acid is formed from 2-chloropropanoic acid, the product
shows no optical activity. Deduce the type of nucleophilic substitution that takes place
and explain your answer. [4]
SN1
Formation of carbocation intermediate is planar by SN1 mechanism
Nucleophile can then attack with equal chance on either side of cation.
Equal chance of both optical isomers being formed = racemic mixture.
Topic 10 Organic Chemistry 10.10
1. This question is about four compounds A, B, C and D. B, C and D can be made from A by the
following reactions. A, B and C are liquid at room temperature, and each compound's molecular
formula is shown.
Sodium was added to each liquid compound. Gas bubbles formed slowly in A but rapidly in C.
(a) Use the information above to identify each of the compounds A, B, C and D, giving the
name and structural formula of each one. [4]
(b) (i) State the type of reaction occurring when A is converted to B and C, and state a
suitable reagent and conditions for the reaction. [3]
(ii) Explain why B is much harder to obtain than C in this reaction. [1]
(c) Identify the gas formed when A and C react with sodium and write an equation for the
reaction of C. Name the other product of the reaction between sodium and C. [4]
(d) Arrange the compounds A, B and C in increasing order of boiling point (lowest boiling point
first). Explain your choice. [4]
(e) None of the compounds A, B, C and D exist as optical isomers. State the structural feature
which is present in a compound that exists as optical isomers. Draw the structural formula of
the isomer of A that exists as optical isomers, [2]
a) A = butanol = CH3CH2CH2CH2OH
B= Butanal = CH3CH2CH2CHO
C = butanoic acid = CH3CH2CH2COOH
D = But-1-ene = CH2=CHCH2CH3
ii) Hard to stop complete oxidation…need to distil product B away from ox agent.
d) butanal….butanol….butanoic acid
butanol = dipole (weaker intermolecular force)
Butanol = H- bonds (stronger intermolecular force)
Butanoic acid = stronger H-bonds + dipole
(iii) Which of the four isomers given in (ii) above is not consistent
with the fact that compound B can be oxidised by an acidified
solution of K2Cr2O7 to give compound C? Explain your answer. [2 marks]
(iv) Give the balanced equation for the reaction of compound B with
ethanoic acid in the presence of sulfuric acid and name the
functional group present in the organic product [3 marks]