Zion and Alwin group of schools

Haloalkane and Haloarene

Assignment Questions
Day-1
1.Compare the dipole moment of the following. CH3F,CH3Cl,CH3Br, CH3I.
2.Haloarenes are less reactive than haloalkanes and haloalkenes, Explain,
3.Why is the solubility of haloalkanes in water very low?
4. Out of o-and p-dibromobenzene which one has higher melting point and why?
5.Give reason
(i )The preparation of ethyl chloride from ethyl alcohol with thionyl chloride is carried in the
presence of pyridine.
(ii)Thionyl chloride
(SOCl2) is preferred for preparing alkanoyl chloride.
(iii)Complete the Reaction
ROH+PCl3→?+?
Day-2
6.Aryl chlorides and bromides can be easily prepared by electrophilic substitution of arenes
with chlorine and bromine respectively in the presence of Lewis acid catalysts, But why
does preparation of aryl iodides requires presence of an oxidising agent?
7. Discuss the role of Lewis acids in the preparation of aryl bromides and chlorides in the
dark.
8.Which of the following compounds (a) and (b) will not react with a mixture of NaBr and
H2S04. Explain why?
(a) CH3CH2CH20H (b)Ph-OH

9.When ethyl chloride react with KCN to form ethyl cyanide as main product.while AgCN
forms isocyanides as the cheif product.Explain.
10.Which of the compounds will react faster in SN1 reaction with the - OH ion?
(i)CH3−CH2−Cl (ii)C6H5—CH2— Cl
Day-3
11.identify the chiral and achiral molecules
(i)2,3-dibromobutane (ii)trans-1,2-dichloro-1,2-ethanediol
(iii)2-butanol
12.Draw other resonance structures related to the following structure and find out whether the
functional group present in the molecule is ortho, para directing or meta directing,

13.Classify the following compounds as primary,secondary and tertiary halides.

(i)IBromobut2en(ii)4Bromopent-2-ene (iii)2 3dibromo2-methyIpropane
14.Which of the products will be major product in the reaction given below? Explain,

CH3CH=CH2 + CH3CH2CH2I + CH3CHICH3

15.Compound A with molecular formulaC4H9Br is treated with aq KOH solution. The rate of this reaction
depends upon the concentration of the compound A only. When another optically active isomer B of this
compound was treated with aq.KOH solution, the rate of reaction was found to be dependent on the
concentration of compound and aq KOH both.(A) Write down the structural formula of both compounds A
and B(B) Out of these two compounds, which one will be converted to the product with inverted configuration.

Day-4

16.Write the structures and names of the compounds formed when compound 'A' with molecular
formula, C7H8 is treated with Cl 2in the presence of FeC13
17.Identify the products A and B formed in the following reaction
(a) CH3 -CH2 -CH=CH-CH3+ HCl—--A+ B
18.Which of the following compounds will have the highest melting point and why?

(1) (11) (111)

19.Write down the structure and IUPAC name for neopentyl bromide,
20.A hydrocarbon of molecular mass 72 g mol- gives a single monochloro derivative and two dichloro
derivatives on photo chlorinatiom Give the structure of the hydrocarbom
Day-5
21.Name the alkene which will yield I-chloro-l-methylcyclohexane by its reaction with
HCI,Write the reactions involved,

22., Which of the following haloalkanes reacts with aqueous KOH most easily? Explain giving
reason, (i) I-Bromobutane (ii) 2-Bromobutane(iii) 2-Bromo-2-methylpropane(iv) 2-Chlorobutane

23.Why can aryl halides not be prepared by reaction of phenol with HCI in the presence of ZnC12?
24. Which of the following compounds would undergo SN1 reaction faster and why?

(B)
25.Allyl chloride is hydrolysed more readily than n-propyl chloride, Why?
Day-6
26.Why is it necessary to avoid even traces of moisture during the use of a Grignard reagent?
27.How do polar solvents help in the first step in SN1 mechanism?
28.Write a test to detect the presence of double bond in a molecule,
29.Biphenyls are potential threat to the environment, How are these produced from aryl haIides?
30.What are the IUPAC names of the insecticide DDT and benzene hexachloride? Why is their use
banned in India and other countries?
DAY-7
31.Elimination reactions (especially ß-elimination) are as common as the nucleophilic substitution
reaction in case of alkyl halides, Specify the reagents used in both cases,
32. Aryl halides are extremely less reactive towa rds nucleophilic substitution, Predict and explain the
order of reactivity of the following compounds towa rds nucleophilic substitution:

33.tert-ButyI Bromide reacts with aq. NaOH by SN1 mechanism while n-butyl bromide reacts by SN2
mechanism. Why?
34.Predict the major product formed when HCI is added to isobutylene. Explain the mechanism involved.
35.Discuss the nature of C—X bond in the haloarenes.
Day-8
36.How can you obtain iodoethane from ethanol when no other iodine containing reagent except Nal is
available in the laboratory?
37.Cyanide ion acts as an ambident nucleophile. From which end it acts as a stronger nucleophile in
aqueous medium? Give reason for your answer.

38.Some alkyl halides undergo substitution whereas some undergo elimination reaction on treatment with
bases. Discuss the structural features of alkyl halides with the help of examples which are responsible for
this difference.

39.Some halogen containing compounds are useful in daily life. Some compounds of this class are
responsible for exposure of flora and fauna to more and more UV light which causes destruction to a great
extent. Name the class of these halo compounds. In your opinion, what should be done to minimise
harmful effects of these compounds.
40. are aryl halides less reactive towards nucleophilic substitution reactions than alkyl halides? How can
we enhance the reactivity of aryl halides?

Day-9

41.An organic compound (A) having molecular formula C3H7Cl reaction with alcoholic solution of KCN
gives compound B. The compound B on hydrolysis with dilute HCl gives compound C. C on reduction
with H2/Ni gives 1-aminobutane. Identify A, B and C.

42.Diphenyls are a potential threat to the environment. How are aryl halides used to form these?

43.An organic compound ‘A’ on heating with NH3 and cuprous oxide at high pressuregives compound
‘B’. The compound ‘B’ on treatment with ice cold solution of HCl gives ‘C” , which on heating with
copper turning and HCl gives ‘A’ again.Identify A, B & C. compound

44.An organic compound ‘A’ having molecular formula C3H6 on treatment with aqueous H2SO4given’ B’
which on treatment with Lucas reagent gives ‘C’. The Compound ‘C’ on treatment with ethanolic KOH
gives back on compound ‘A’. Identify A,B, & C.

45.Why iodoform has appreciable antiseptic property?

Day-10

46.Consider the following reaction sequence,CH3CCH in presence of aq.H2SO4 and HgSO4 gives A .A on
reaction with PCl5 with Heat gives B.

47.Which of the following compounds will give a positive iodoform test?A. C2H5OH B. CH3CHO
C.CH3OH D. HCHO

48. Find the major product: (a)C6H5CCl​3(Cl2,FeCl3​)-​----------->??

(b) why the boiling point of haloalkanes are higher than the parent hydrocarbon of comparable molecular
mass
49.The substitution reaction of alkyl halide mainly occurs by SN1 or SN2 mechanism. Whatever
mechanism alkyl halides follow for the substitution reaction to occur, the polarity of the carbon halogen
bond is responsible for these substitution reactions. The rate of SN1 reactions are governed by the
stability of carbocation whereas for SN2 reactions steric factor is the deciding factor. If the starting
material is a chiral compound, we may end up with an inverted product or racemic mixture depending
upon the type of mechanism followed by alkyl halide. Cleavage of ethers with HI is also governed by
steric factor and stability of carbocation, which indicates that in organic chemistry, these two major
factors help us in deciding the kind of product formed.

1. Predict the stereochemistry of the product formed if an optically active alkyl halide undergoes
substitution reaction by SN2 mechanism.

2. Write the structures of the products formed when anisole is treated with HI.

3. Predict the major product formed when 2-Bromobutane undergoes a reaction with alcoholic KOH.

4. Name the instrument used for measuring the angle by which the plane of polarised light is rotated.

5. Give one use of CHI3.

50. Chloroflouro carbon (CFC) compounds of methane and ethane are collectively known as freons. They
are non-imflammable , extremely stable, non-toxic, non-corrosive and low boiling liquids. CFC and gas
emitted from the exhaust system of supersonics aeroplanes might be slowly depleting the concentration of
the ozone layer in the upper atmosphere.

1. Write the formula of freon-12.

2. Give two uses of chloroflourocarbons.

3. How does freon-12 deplete ozone layer?

4. Do you think the use of CFCs be banned? Give a reason.

5. Name some other substitutes for freons