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Eapcet Pyqs - Haloalkanes and Haloarenes
Eapcet Pyqs - Haloalkanes and Haloarenes
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(1)
(2)
(3)
(1)
(2)
(3)
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(1)
(2)
(3)
(1)
(2)
(3)
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+
I. n − Pentylbromide ⎯Zn ⎯⎯ /H
→P
II. n − Pentylbromide ⎯⎯⎯⎯Na
Dry Ether
→Q
(1) Pentane; Decane
(2) Pent-1-ene; Decane
(3) Pentane; Pentane
(4) Pentane; 1-Decene#[AP EAMCET-06.07.2022, Shift-II]#
10. The order of decreasing reactivity towards an electrophilic reagent, for the following
compounds, is
I. Benzene II. Toluene
III. Chlorobenzene IV. Phenol
(1) I II III IV
(2) II IV I III
(3) IV III II I
(4) IV II I III#[TS EAMCET-19.07.2022, Shift-II]#
11. Sodium tertiary butoxide on reaction with methyl bromide produced the product P .
Sodium methoxide upon reaction with tertiary butyl bromide generated the product Q
.
The products P and Q are
(1)
(2)
(3)
12. The order of reactivity of the following compounds towards dilute aqueous KOH in
S N 1 reaction is
CH3CH 2CH 2CH 2Br H 3CCH 2CHBrCH (CH3 ) CHCH 2Br (CH 3 )3 CBr
I II III IV
(1) I IV III II
(2) IV II III I
(3) III II I IV
(4) I III II IV#[TS EAMCET-18.07.2022, Shift-II]#
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20. The correct order of reactivity of hydrogen halides with ethyl alcohol is
(1) HF HCl HBr HI
(2) HCl HBr HF HI
(3) HBr HCl HI HF
(4) HI HBr HCl HF #[AP EAMCET-2008]#
(3) C6 H 5CH ( CH 3 ) Br
23. Which of the following can give a Grignard reagent when reacted with magnesium in
dry ether?
(1) C2 H6
(2) C2 H5Cl
(3) C2 H5OH
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25. Identify the most suitable reagents (I) and (II) for the following sequence of reactions:
26. The compound which readily under goes bimolecular nucleophilic substitution reaction
with aqueous KOH is
(1)
(2)
(3)
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X + 2HI ⎯⎯ → 2Y + H 2 O
(1) C2H6
(2) C2 H5I
(3) C2H4
(4) C2H5OC2H5 #[AP EAMCET-2007]#
Codes
(1) A-5, B-3, C-4, D-1
(2) A-1, B-2, C-3, D-4
(3) A-3, B-4, C-1, D-2
(4) A-4, B-1, C-2, D-5 #[AP EAMCET-2007]#
29. Which of the following is added to chloroform to slow down its aerial oxidation in
presence of light?
(1) Carbonyl chloride
(2) Sodium hydroxide
(3) Ethyl alcohol
(4) Nitric acid#[AP EAMCET-2006]#
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31. Which one of the following is not a method for preparing chloroform?
(I) Heating ethyl alcohol with chlorine and alkali.
(II) Heating acetone with bleaching powder and water.
(III) Heating chloral hydrate with aqueous sodium hydroxide.
(IV) Distillation of acetone over iron filing and water.
(1) II
(2) I
(3) III
(4) IV#[AP - EAMCET(MEDICAL) - 2009]#
32. Hydrogen chloride and SO2 are the side products in the reaction of ethanol with thionyl
chloride. Which of the following is the main product in this reaction?
(1) C2H5OC2 H5
(2) C2H6
(3) CH3Cl
(4) C2 H5Cl #[AP EAMCET (Engg.)-2005]#
34. The chlorination of ethane is an example for which type of the following reactions?
(1) Nucleophilic substitution
(2) Electrophilic substitution
(3) Free radical substitution
(4) Rearrangement#[AP EAMCET (Engg.) - 2012]#
36. What by product is formed in the process of making phenol from cumene ?
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(1) propan-2-ol
(2) n-propanol
(3) propanal
(4) propan-2-one#[AP EAMCET (Engg.) 21.09.2020, Shift-I]#
37. Which among the following statements is true about reactivity of haloarenes towards
nucleophilic substitution reactions?
1.Haloarenes are very reactive towards nucleophilic substitution reaction.
2.In haloarenes, the C − X bond acquires partial doubled bond character.
3.The C − X bond in haloarenes is longer than the C − X bond in haloalkanes.
4.In haloarenes, the phenyl cation formed as a result of self-ionisation is stable.
(1) 1
(2) 2
(3) 3
(4) 4#[AP EAMCET (Engg.) 18.9.2020 Shift-I]#
38. With respect of chlorobenzene, which of the following statements is not correct?
(1) Cl is ortho/para directing
(2) Cl exhibits + M effect
(3) Cl is ring deactivating
(4) Cl is meta directing#[AP EAMCET (Engg.) - 2012]#
(1)
(2)
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(3)
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ANSWER
1. 3 2. 1 3. 4 4. 4 5. 3
6. 3 7. 3 8. 1 9. 1 10. 4
11. 2 12. 4 13. 4 14. 2 15. 1
16. 4 17. 1 18. 1 19. 3 20. 4
21. 3 22. 1 23. 2 24. 2 25. 4
26. 4 27. 2 28. 3 29. 3 30. 3
31. 4 32. 4 33. 1 34. 3 35. 3
36. 4 37. 2 38. 4 39. 4 40. 2
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EXPLANATION
1. (C) : Aromatic carboxylic acids do not undergo Friedel-crafts reaction because the -
COOH group is deactivating and the catalyst AlCl3 gets bonded to COOH group.
−COOH group is Meta directing because it is electron withdrawing group with − R effect.
There is +ve charge on ortho and para positions. So, electrophilic substitution takes place at
Meta position. Here, both statements are true but statement II is not correct explanation of
statement I.
2. (A) : On the surface of polar stratospheric clouds, hydrolysis of chlorine nitrate reaction
is given below-
ClONO2 + H2O → HOCl + HNO3
A B
Reaction of chlorine nitrate with HCl-
ClONO2 + HCl → Cl 2 + HNO3
C B
So, the correct option is (a)
3. (D) : Infriedel-crafts alkylation of aniline, one gets positively charged nitrogen at
benzene ring.
−
4. (D) : The correct order of nucleophilicity is NH 2 NH3
Nucleophilicity referred as nucleophile strength. A nucleophile is a chemical species that forms
−
bonds by donating an electron pair. Here, NH 2 is stronger nucleophile than NH3 because of
the charge on the amide ion.
5. (C)
6. (C) :
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is inactive towards SN1 reaction because halogen is attached to bridge head carbon atom,
where formation of carbocation is not possible.
7. (C) :
9. (A) :
(i) CH 3 − ( CH 2 )4 − Br ⎯⎯⎯ → CH 3 − ( CH 2 )2 − CH 3 + HBr
+
Zn / H
Pentane
Alkyl halide (except Fluorides) on reduction with zinc dilute hydrochloric acid give alkanes.
Hence, n-pentyl bromide gives pentane.
(ii) CH 3 − ( CH 2 )4 − Br ⎯⎯⎯ → CH 3 − ( CH 2 )8 − CH 3 + HBr
+
Zn / H
Decane
When two alkyl halides are reacted with sodium metal in dry ether solution to form a higher
alkane.
10. (D) : The structure of compound are given below
As we know that electrophile attack that position in which the electron density will be more.
CH3 , OH are ring activating group. It increases electron density on benzene ring that's why it
has more reactivity towards electrophilic reagent. So, the overall electrophilic reagent towards
reactivity as given below:-
Phenol (IV) > Toluene (II) > Benzene (I) > Chlorobenezene (III)
11. (B) :
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12. (D) : When these compound are react towards aqueous KOH it is a nucleophilic
substitution reaction which result in formation of carbocation.
Stability of carbocation is 3 2 1
So, the correct option is I III II IV
13. (D) : Dry ether is the most suitable solvent forwurtz reaction.
Wurtz are also known as warts coupling. It is method used to synthesize higher alkanes by a
reaction between alkyl halides and metallic sodium I the presence of dry ether.
14. (B) : Alc. KOH act as a dehydrohalogenation agent by reacting with an alkyl halide and
forms alkene as a product. The reaction is-
CH3CH 2CH 2CH 2Cl ⎯⎯⎯⎯ Alc.KOH
→ CH3CH 2CH = CH 2
1-chlorobutane 1-butene
Hence, option (b) is correct.
15. (A) :
18. (A) : The boiling point of alkyl halides decreases due to alkyl branching. Branching of
chain makes the molecule more compact and surface area decreases.
The highest boiling point is CH3 − CH2 − CH2 − CH2Cl .
19. (C) :
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21. (C) : Ethyl chloride react with moist Ag2O (silver oxide) to give the ethanol ( C 2 H 5 OH )
and ethanol further react with Al2O3 to a temperature of 360 C and form the ethene. Ethene
on reaction with S2Cl2 , mustard gas is formed.
C2 H 5Cl ⎯⎯⎯
Moist
Ag 2O
→ C2 H 5 − OH ⎯⎯⎯
Al 2O3
360 C
→ CH 2 = CH 2 ⎯⎯⎯
S 2Cl 2
→ ClCH 2 − CH 2 − S − CH 2 − CH 2Cl
Ethyl chloride Ethanol eEthene Mustard Gas
(a)
(b)
(c)
(d)
On the basis of stability of carbocation,
(a) (d) (c) (b)
( C6 H5 )2 C ( CH3 ) Br is more readily hydrolyzed by SN1 mechanism.
23. (B) : When ethyl chloride reacted with magnesium in dry ether then the Grignard
reagent is formed.
CH 3 − CH 2 − Cl + Mg ⎯⎯⎯ ⎯
Dryether
→ CH 3CH 2MgCl
Ethylchloride Ethylmagnesium chloride
24. (B) : It is used for easy production of alkyl iodide. It can be used as a qualitative test to
determine from which class an unknown alkyl halidebelong to synthesis of chrysochlamic acid
is also done by finkelstein reaction.
25. (D) : The given sequence of reactions give the following product-
26. (D) :
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In above compound −NO2 group is electron withdrawing group so the bond strength is
decreases between benzene ring and Cl . So the compound undergo ( SN 2 ) bimolecular
nucleophilic substitution reaction.
27. (B) :
C2H5I + NaOC2H5 ⎯⎯ → C2H5OC2H5 + NaI
( x)
C2H5OCH5 + 2HI ⎯⎯
→ 2C2 H5I + H 2O
(x) ( x)
28. (C) :
Reactants Products
31. (D) : Distillation of acetone over iron filings and water cannot produce chloroform.
32. (D) : The reaction of ethanol withthionylchloride gives the ethyl chloride ( C 2 H 5Cl ) ,
hydrogen chloride and SO2 .
C2H5 − OH + SOCl 2 → C2H5Cl + SO2 + HCl
Ethylalcohol Thionyl Ethylchloride
chloride
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Chlorination of ethane involves free radical substitution in the presence of light to form ethyl
chloride.
35. (C) :
Because of + R effect of Cl -atom with the ring, C − Cl bond in chlorobenzene gets a double
bond character and it becomes shorter and stronger than the C − Cl bond of in methyl chloride
( CH 3 − Cl ) , which does have such effect.
36. (D) : Cumene (isopropyl benzene) is oxidised in the presence of air to form cumene
hydroperoxide. On treating with dilute acid, it is converted to phenol and acetone.
37. (B) : Because of + R effect of halogen atom X , the C − X bond of haloarene acquires
partial double bond character C − X bond becomes shorter than that in haloalkanes) and
nucleophilic substitution becomes difficult.
38. (D) : The lone pair of electron on chlorine is involved in delocalization with benzene
ring and increase the electron density at ortho and para position. So, Cl is not meta directing.
It so, + M effect due to non-bonding electron and it is deactivating due to high electro
negativity.
39. (D) :
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40. (B):
C2H5OH + 4I 2 + 3Na2CO3 → CHI3 + HCOONa + 5NaI + 3CO2 + 2H 2O
( X)
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