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ScoreChem 962/3
Set 5 (08)
SECTION A
1. What is the product when propene is oxidised with cold dilute potassium manganate(VII)?
A CH3CH(OH)CH2OH
B CH3CH2CH2OH
C CH3CH2CHO
D CH3COCH3
2. The structural formula of a compound is as follows.
CH3C = CHCH2CHCH2CHO | | CH3 CH3
What is its IUPAC name?
A 2,5-dimetylhept-2-enal
B 3,6-dimetylhept-2-enal
C 2,5-dimetylhept-5-enal
D 3,6-dimetylhept-5-enal
3. How many total alkenes (including stereoisomers) are possible for the product of the following reaction? heatCH3 CH(CH3) CHBr CH2CH2CH3 ALKENES
alcoholic KOH
A 2 B 3C 4 D 5
4. Which of the following species can act as a nucleophile?
A CH3 B Br+
C AlCl3 D CN-
5. Which of the following reagent is used to distinguish phenol from phenylmethanol?
A Ethanoyl chloride
B Chloroethane
C Bromine water
D Iodine solution
6. Which pair of reagents cannot be used to prepare CH3CH2Cl?
A CH2 = CHCl + H2
B CH3CH2OH + HCl
C CH3CH2OH + Cl2
D CH3CH2NH2 + Cl2
7. Z , with a formula of
gives an orange precipitate with 2,4-DNPH reagent, no precipitate with Fehling’s solution and no reaction with phosphorous pentachloride. It contains a chiral carbon atom. The C4H7O group in the molecule Z could be
HO
C4H7O
A CH2 = C – CH(OH)CH3
|
O = C – CH(CH3) CH3
|CH3 – CH CO CH3
|CH3 – C(CH3) CHO |
B
C D
8. Which of the following compounds reacts easily with cold water?
Cl CH2Cl CH3CH2 Cl
CH3CH2 COCl
A B C
D
9. What is the principal product from the following series of reactions?
LiAlH4 PBr3 KCN LiAlH4
Ether Alcohol Ether Ether heat
COOH
CH2NH
2
CH2 CH2 NH2 CH2CONH
2
CH2CH(OH)NH2
A
C
B
D
10. Which of the following is not true
for proteins?
A They are natural condensation
polymers
B They are built up from identical
monomer units
C They are able to be hydrolysed
D They are built up from amino
acids
11. Adrenaline has the following formula
Which of the following statements about adrenaline is correct?
A It is a primary amineB It is chiral and contains three alcohol groupsC It is chiral and contains two phenol groupsD It exhibits cis-trans isomerism
HO
CH(OH)CH2NHCH3H
O
12. Nylon-6,6 can be made by condensation polymerisation of a compound X and hexane-1,6-diamine.
-(--- N – C – (CH2)4 – C – N – (CH2)6 – N – C ---)- | || || | | || H O O H H O
Compound X could be
A hexane-1,6-diolB hexanedioyl chlorideC potassium hexanedioateD hexanoic acid
13. The principle product formed when hydrogen iodide reacts with prop-1-ene is 2-iodopropane rather than 1-iodopropane. Which of the following statements is correct regarding this observation?
A Production of 2-iodopropane proceeds at a higher rate than that leading to the production of 1-iodopropane
B Production of 2-iodopropane proceeds via a primary carbonium
C Production of 2-iodopropane proceeds via a secondary carbonium
D 2-iodopropane is more stable than 1-iodopropane
14.The organic compounds which are expected to decolourise bromine water include
I CH3CH = CH COOH
II CH3CH(OH) CH2CH3
III C6H5 – OH
A I and II B I and III C II and III D I, II and III
15.Which of the following statements suggests the presence of free radicals in the bromination of methylbenzene?
I The reaction proceeds most quickly in sunlight
II Hydrogen bromide is present in the product
III Bromomethylbenzene is formed as the first product
A I only B I and II C I and III D II and III
1. What is the product when propene is oxidised with cold dilute potassium manganate(VII)?
A CH3CH(OH)CH2OH
B CH3CH2CH2OH
C CH3CH2CHO
D CH3COCH3
2. The structural formula of a compound is as follows.
CH3C = CHCH2CHCH2CHO | | CH3 CH3
What is its IUPAC name?
A 2,5-dimetylhept-2-enal
B 3,6-dimetylhept-2-enal
C 2,5-dimetylhept-5-enal
D 3,6-dimetylhept-5-enal
3. How many total alkenes (including stereoisomers) are possible for the product of the following reaction? heatCH3 CH(CH3) CHBr CH2CH2CH3 ALKENES
alcoholic KOH
A 2 B 3
C 4 D 5
4. Which of the following species can act as a nucleophile?
A CH3 B Br+
C AlCl3 D CN-
5. Which of the following reagent is used to distinguish phenol from phenylmethanol?
A Ethanoyl chloride
B Chloroethane
C Bromine water
D Iodine solution
6. Which pair of reagents cannot be used to prepare CH3CH2Cl?
A CH2 = CHCl + H2
B CH3CH2OH + HCl
C CH3CH2OH + Cl2
D CH3CH2NH2 + Cl2
7. Z , with a formula of
gives an orange precipitate with 2,4-DNPH reagent, no precipitate with Fehling’s solution and no reaction with phosphorous pentachloride. It contains a chiral carbon atom. The C4H7O group in the molecule Z could be
HO
C4H7O
A CH2 = C – CH(OH)CH3
|
O = C – CH(CH3) CH3
|CH3 – CH CO CH3
|CH3 – C(CH3) CHO |
B
C D
8. Which of the following compounds reacts easily with cold water?
Cl CH2Cl CH3CH2 Cl
CH3CH2 COCl
A B C
D
9. What is the principal product from the following series of reactions?
LiAlH4 PBr3 KCN LiAlH4
Ether Alcohol Ether Ether heat
COOH
CH2NH
2
CH2 CH2 NH2 CH2CONH
2
CH2CH(OH)NH2
A
C
B
D
10. Which of the following is not true
for proteins?
A They are natural condensation
polymers
B They are built up from identical
monomer units
C They are able to be hydrolysed
D They are built up from amino
acids
11. Adrenaline has the following formula
Which of the following statements about adrenaline is correct?
A It is a primary amineB It is chiral and contains three alcohol groupsC It is chiral and contains two phenol groupsD It exhibits cis-trans isomerism
HO
CH(OH)CH2NHCH3H
O
12. Nylon-6,6 can be made by condensation polymerisation of a compound X and hexane-1,6-diamine.
-(--- N – C – (CH2)4 – C – N – (CH2)6 – N – C ---)- | || || | | || H O O H H O
Compound X could be
A hexane-1,6-diol
B hexanedioyl chloride
C potassium hexanedioateD hexanoic acid
13. The principle product formed when hydrogen iodide reacts with prop-1-ene is 2-iodopropane rather than 1-iodopropane. Which of the following statements is correct regarding this observation?
A Production of 2-iodopropane proceeds at a higher rate than that leading to the production of 1-iodopropane
B Production of 2-iodopropane proceeds via a primary carbonium
C Production of 2-iodopropane proceeds via a secondary carbonium
D 2-iodopropane is more stable than 1-iodopropane
14.The organic compounds which are expected to decolourise bromine water include
I CH3CH = CH COOH
II CH3CH(OH) CH2CH3
III C6H5 – OH
A I and II B I and III C II and III D I, II and III
15.Which of the following statements suggests the presence of free radicals in the bromination of methylbenzene?
I The reaction proceeds most quickly in sunlight
II Hydrogen bromide is present in the product
III Bromomethylbenzene is formed as the first product
A I only B I and II C I and III D II and III
SECTION BARE YOU READY??
Q16 [8 marks]
(a) Paracetamol and aspirin have analgesic (pain killing) action and are readily absorbed from the intestines.
CH3CONH OH
COOH
O – C – CH3
O
Paracetamol
Aspirin
Each drug is easily hydrolysed by enzymes in the intestine. For each drug, name the group which is hydrolysed. [2 marks]
(b) Adrenalin is a hormone which, when secreted directly into the bloodstream, acts as a stimulant. It has the structure as below.
HO
HO
CH – CH2 – NHCH3OH
(i) Name three functional groups present in the adrenalin molecule. [3 marks] (ii) By means of asterisk, identify the chiral centre in the structure of adrenalin drawn above.
[1 mark]
Q16
HO
HO
CH – CH2 – NHCH3OH Adrenalin
(iii) The synthesis of adrenalin includes the following stages:
HO
HO
CHO
A B Adrenalin
Give the full structure formulae of A and B. [2 marks]
Q16
HCN H2, Ni
Q17 [7 marks](a) H2N – CH(CH3)COOH H2N – CH2COOH Alanine Glycine
(i) Name the functional groups present in the amino acids given above.
[2 marks](ii) Draw the structure of the
zwitterions for alanine.[1 mark]
(iii) Write a reaction equation to show what would happen when alanine dissolves in hydrochloric acid.
[1 mark] (iv) Draw one structural formula for the dipeptide formed between alanine and glycine.
[1 mark]
Q17(b) The synthetic rubber SBR is a copolymer of styrene (phenylethene) and buta-1,3-diene in the ratio of 3 : 1.
(i) Draw the structure of SBR. [1 mark]
(ii) What is the type of polymerisation used to produce SBR?
[1 mark]
Q16
A B
HO
HO
CHCN
OH
(a) Paracetamol = amide, aspirin = ester
(b)(i) Phenol, Hydroxy, Amino
(ii) – *CH(OH) – CH2 – NHCH3
(iii)
HO
HO
CHCH2NH2OH
(a) 1 amino group
2 carboxyl group
3 +H3N – CH(CH3) COO –
4 H2N-CH(CH3)COOH + HCl
ClH3N- CH(CH3)COOH
5 H2N – CH(CH3) – CONH – CH2COOH
OR H2N – CH2 – CONH – CH(CH3)COOH6 [peptide link] C – N
|| | O H
(b)1 --(-- CH – CH --)3-(-- CH2CH = CHCH2 --)--
2 addition polymerization
Q17
SECTION CARE YOU REALLY READY??
Q18An organic compound, Z, has the following composition by mass:
C, 62.1% H, 10.3% O, 27.6%
(a) Determine the empirical formula of Z. [3 marks]
(b) Z has three isomers, E, F and G. E is an alcohol, F is a ketone and G is an aldehyde. Draw possible structural formulae for E, F and G.
[3 marks]
Q18(c) Describe tests that would allow you to show that:
(i) E is an alcohol, whereas F and G are not,
[3 marks]
(ii) F and G are carbonyl compounds, whereas E is not,
[3 marks]
(iii) G is aldehyde, whereas E and F are not. [3 marks]
Q19(a)
Dopamine
(i) Draw a structure of the product formed when dopamine reacts with warm dilute nitric acid.
[1 mark]
(ii) Explain any type of reaction which takes place.
[4 marks]
HO
CH2CH2NH2
HO
(b) Dopamine can be synthesised from the following compound.
Outline a scheme of reactions illustrates the synthesis of dopamine. State reagents and conditions required. [5 marks]
HO
CH3
HO
(c) Compounds R and S are two isomers with molecular formula C8H10O. R gives off white fumes with thionyl chloride and forms a yellow precipitate with alkaline aqueous iodine but S does not. S dissolves in aqueous potassium hydroxide but R does not.
Explain the above observations and write the structural formulae of R and S.
[5 marks]
C
(a)
Element C H O
1 moles of 62.1/12.0 10.3 /1.0 27.6
/16.0
2 Ratio 3 6 1
3 empirical formula C3H6O
(b)
1 E CH2 = CH CH2OH OR CH2
= C(OH) CH3
2 F CH3 CO CH3
3 G CH3CH2CHO
Q18
(C) [9 marks]
1,2 [E=alcohol] PCl5 r.t. / Na, r.t.
3 white fumes, HCl / effervescence occurs, H2
4,5 [F, G=carbonyl]
2,4-dinitrophenylhydrazine, heat
6 orange ppt
7,8 [G=aldehyde] Tollen’s reagent, heat
/ Fehling solution, heat
9 silver mirror / reddish brown ppt formed
Q18
Q19
1
2 acid – base reaction / neutralisation
3 NH2 (amino) group is basic due to the lone
pair electrons on N
4 electrophilic substitutions
5 OH (phenol) group activates the benzene
ring / benzene ring is richer in electron
density
/ lone pair electrons from O delocalized
into
benzene ring
HO
CH2CH2NH3+
HO
NO2
NO2O2N
Q19
(b) [5 marks]
1 Cl2, UV
2 [product] - CH2Cl
3 KCN / alcohol, reflux
4 [product] - CH2CN
5 H2, Ni, 180C /
LiAlH4 in dry ether followed by acidic
hydrolysis
(c) [5 marks]
1 [R gives off white fumes with SOCl2]
R has OH group / R is an alcohol
2 [R forms yellow ppt with I2/NaOH]
R has a structure of – CH(CH3)OH
3 [S dissolves in KOH]
S is acidic / S is a phenol
4 R is C6H5 – CH(OH)CH3
5 S is HO – C6H4 – CH2CH3or
HO – C6H3 – (CH3)2
Q19
Sigh! Why didn’t I study hard from the beginning??
YES!! I GOT IT.