CHEMISTRY TEST FOR S5
I. ANSWER BY TRUE OR FALSE
1. Chloroform is employed as a solvent in paint remover.
2. Iodoform was used earlier as an antiseptic.
3. Methyl chloride, methyl bromide, ethyl chloride and some chlorofluoromethanes are gases at room
temperature.
4. The objects which are non-superimposable on their mirror image (like a pair of hands) are said to be
chiral and this property is known as [Link] the objects, which are superimposable on their
mirror images are called achiral.
5. CHCl3 (chloroform): is used as insecticide
6. DDT: Dichloro diphenyl trichloroethane is used as anaesthesia
7. Halogenoalkanes , although they dissolve more than alkanes, are only slightly soluble in water.
8. Halogenoalkanes undergo nucleophilic substutition reactions in which the halogen atom is replaced by a
nucleophile.
9. Elimination reaction is where a saturated organic compound loses an atom or group of atoms attached to
form unsaturated organic compound.
II. MULTIPLE CHOICE QUESTIONS
1. Which of the following is not a halogenoalkane compound:
a. Tribromobenzene
b. 3-iodohexane
c. 2-chloro-3-methylpentane
d. 2-bromopentane
2. Which of the following compounds will undergo an Sn2 reaction most readily?
a. (CH3)3CCH2I
b. (CH3)3CCl
c. (CH3)2CHI
d. (CH3)2CHCH2CH2CH2I
e. (CH3)2CHCH2CH2CH2Cl
3. Sn2 reactions involving chiral electrophiles usually proceed with:
a. inversion of configuration
b. slightly more inversion than retention.
c. slightly more retention then inversion.
d. retention of configuration.
e. equal amounts of inversion and retention of configuration.
4. Which compound undergoes solvolysis in aqueous ethanol most rapidly and why?
Remember: solvolysis refers to ionization of the molecule aided by the solvent.
a. cyclohexyl bromide
b. isopropyl chloride
c. methyl iodide
d. 3-chloropentane
e. 3-iodo-3-methylpentane
5. Which of the following alkyl halides is most likely to undergo rearrangement in an Sn1 reaction?
a. 3-bromopentane
b. 2-chloro-3,3-dimethylpentane
c. 3-chloropentane
d. bromocyclohexane
6. Which C-X bond has the highest bond energy per mole?
a) C-Br
b) C-Cl
c) C-F
d) C-I
7. Which alkyl halide has the highest reactivity for a particular alkyl group?
a) R-F
b) R-Cl
c) R-I
d) R-Br
8. When ethyl chloride reacts with nascent hydrogen, what is the formed product?
a) Methane
b) Propane
c) Butane
d) Ethane
9. Which alkyl halide out of the following may follow both SN1 and SN2 mechanism?
a) CH3-X
b) (CH3)2CH-X
c) (CH3)3C-X
d) (CH3)3C-CH2-X
10. When two moles of ethyl chloride react with two moles of sodium in the presence of ether what will be
formed?
a) 2 moles of ethane
b) 1 moles of ethane
c) 2 moles of butane
d) 1 moles of butane
11. Which of the following halide can give best SN2 reaction?
a) Primary alkyl halide
b) Tertiary alkyl halide
c) Secondary alkyl halide
d) All can give SN2 reaction at same rate
12. Why alkyl halides are considered to be very reactive compounds towards nucleophile?
a) they have an electrophilic carbon & a bad leaving group
b) they have a nucleophilic carbon & a good leaving group
c) they have an electrophilic carbon
d) they have an electrophilic carbon & a good leaving group
13. In primary alkyl halides, carbon attached to the halogen atom is further attached to how many carbon
atoms?
a) 1 b) 2 c) 3 d) 4
14. Which of the following is not the method of preparation of alkyl halide?
a) Wurth method
b) Halogenation of alkene
c) Addition of HX on alkenes
d) Hydration of alkene
15. Which of the following reactant gives the best method of preparation of alkyl halides when reacts with
alcohol?
a) Zn/HCl
b) PCl5
c) SOCl2/ Pyridine
d) PCl3
16. Which is the correct increasing order of boiling points of the following compounds? 1-iodobutane,
1-bromobutane, 1-chlorobutane, Butane
(a) Butane < 1-chlorobutane < 1-bromobutane < 1-iodobutane
(b) 1-iodobutane < 1-bromobutane < 1-chlorobutane < Butane
(c) Butane < 1-iodobutane < 1-bromobutane < 1-chlorobutane
(d) Butane < 1-chlorobutane < 1-iodobutane < 1-bromobutane
17. A primary alkyl halide would prefer to undergo………
(a) SN1 reaction
(b) SN2 reaction
(c) an elimination
(d) racemization
18. SN1 reaction undergoes through a carbocation intermediate as follows:
organic-chemistry-questions-answers-nucleophilic-substitution-reaction-q3 [R = t-Bu, iso-Pr, Et, Me] (X
= Cl, Br, I) The correct statements are:
I. The decreasing order of rate of SN1reaction is t-BuX > iso-PrX > EtX > MeX
II. The decreasing order of ionization energy is MeX > EtX > iso-PrX > t-BuX
III. The decreasing order of energy of activation is t-BuX > iso-PrX > EtX > MeX
a) I & II are correct
b) I & III are correct
c) II and III are correct
d) I, II & III are correct
III. OPEN QUESTIONS
1. Name the following halides according to IUPAC system and classify them as primary, secondary or tertiary
halogenoalkanes
a. (CH3)2CHCHClCH3
b. CH3CH2C(CH3)2CH2I
c. (CH3)3CCH2Br
d. CH3CH(CH3)CHBrCH3
e. CH3CH=CHC(Br)(CH3)2
f. CH3CH=C(Cl)CH2CH(CH3)2
2. CFC's, chlorofluorocarbons (CF2Cl2), saw widespread use as refrigerants and as aerosols. However, due to
their low boiling point, when sprayed into the air they rise up to the atmosphere and are exposed to large
amounts of uv radiation. This light, often seen as hv in chemical equations, provides the energy needed to
break the CFC's into radicals. Chlorine radicals are formed and this degrades the protective layer of ozone
into oxygen, O2. Draw the formation of the chlorine radical from a CFC and show how ozone molecule is
destroyed by these chemicals.
3. This question is concerned with the six reactions shown in the following scheme. The four compounds
involved are represented by their molecular formulae and labelled using the letters A, B, C and D.
(a) State the names of the three homologous series to which compounds A, B and C belong.
(b) Give the name of the type of reaction occurring in each of the following conversions:
i. compound A to compound B;
ii. compound B to compound C;
iii. compound C to compound D;
iv. compound D to compound C;
v. compound C to compound B;
vi. compound B to compound A;
(c) Give the name or formula of reagent X and state the different conditions under which it
would be used in the conversions of compound B to compound C, and of compound B to
compound A.
(f) Write an equation for each of the following reactions:
(d) the conversion of compound B to compound A;
(e) the conversion of compound B to compound C.
(g) Outline a possible mechanism for the conversion of compound B to compound C.
4. (a) The compound 1,2-dibromo-1,1,2,2-tetrafluoroethane is used in some fire extinguishers. Draw the
structure of this compound.
(b) Halothane is used as an anaesthetic and has the following structure.
i. Give the systematic name of halothane.
ii. Calculate the Mr of halothane.
iii. Calculate the percentage by mass of fluorine in halothane.
5. (a) Give the structural formula of 2-bromo-3-methylbutane.
(b) Write an equation for the reaction between 2-bromo-3-methylbutane and dilute aqueous
sodium hydroxide. Name the type of reaction taking place and outline a mechanism.
(c) Two isomeric alkenes are formed when 2-bromo-3-methylbutane reacts with ethanolic
potassium hydroxide. Name the type of reaction occurring and state the role of the reagent. Give the
structural formulae of the two alkenes.
6. (a) Ethanenitrile can be made by reacting chloromethane with potassium cyanide.
i. Write an equation for this reaction.
ii. Name the mechanism for this reaction.
iii. Explain, in terms of bond enthalpies, why bromomethane reacts faster than chloromethane
with potassium cyanide.
(b) Chloromethane can react with ammonia to produce a primary amine.
7. (a) What feature of the chloromethane molecule makes it susceptible to be attacked by an ammonia
molecule?
(b) Outline a mechanism for this reaction.
8. Consider the reaction of (CH3)3CO- with iodomethane. Will the reaction rate increase, decrease, or
remain the same if the concentration of iodomethane is increased? Explain.
9. Why does CH2=CHCHBrCH3 undergo solvolysis much more rapidly than 2-bromobutane?
10. Arrange the substrates in order of increasing Sn2 reactivity with NaCN: Bromoethane,
1-chloro-3,3-dimethylpentane, 1-chloro-2,2-dimethylpentane, and 2-bromo-2-methylpentane.
11. Arrange the following compounds in order of increasing reactivity toward ethanol solvolysis: t-butyl
bromide, t-butyl iodide, isopropyl chloride, and methyl iodide.
12. What combination of reactants would be best to prepare CH3OCH(CH3)2 by an Sn2 reaction?
13. For the reaction between 2-bromopropane and potassium cyanide:
(a) give the name or formula of the attacking species involved;
(b) give the name of the mechanism involved;
(c) write an equation for the reaction;
14. Why does 1-bromopropane react with nucleophiles but propane does not?
15. Write the equations for the preparation of 1-iodobutane from:
a. 1-butanol,
b. 1-chlorobutane,
c. but-1-ene
16. Arrange the compound of each set in order of reactivity towards SN2 displacement:
a. 2-bromo-2-methylbutane, 1-bromopentane, 2-bromopentane
b. 1-bromo-3-methylbutane, 2-bromo-2-methylbutane, 3-bromo-2-methylbutane
c. 1-bromobutane,1-bromo-2,2-dimethylpropane,1-bromo-2-methylbutane,1-bromo-3-thylbutane.
17. a) There are four structural isomers of molecular formula C4H9Br. The formulae of two of these
isomers are given.
CH3CHBr(CH3)2 Isomer 1 CH3CH2CHBrCH3 Isomer 2
Draw the remaining two structural isomers.
i. Give the name of isomer 2
b) All four structural isomers of C4H9Br undergo similar reactions with ammonia
i. Give the name of the mechanism involved in these reactions.
ii. Draw the structural formula of the product formed by the reaction of isomer 2 with
ammonia.
iii. Select the isomer of molecular formula C4H9Br that would be most reactive with
ammonia. State the structural feature of your chosen isomer that makes it the most reactive
of the four isomers.
iv. The elimination of HBr from Isomer 1 produces two structural isomers, compounds A and
B.
1. Give the reagents and conditions required for this elimination reaction.
2. Give the structural formulae of the two isomers, A and B formed by elimination of
HBr from isomer 1.
18. (a) Using suitable examples, define the terms:
i. Nucleophile
ii. Substitution
(b) Why are halogenoalkanes attacked by nucleophiles?
19. Use of CFCs has been declining due to concern over the possible effects on the environment. It is thought
that this damage is a result of a light catalysed radical process involving chlorine radicals.
a. State one possible type of damage caused by CFCs to the environment.
b. Explain what is meant by a radical.
c. Give an equation for the formation of a radical from the chlorofluorocarbon CCl2F2
20. Give the major product (with proper explanation) when following halogen compound is treated with sodium
ethoxide (CH3CH2ONa).
