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OrganicFor Board Examinations

Chemistry

Performance Booster

By

AJNISH GUPTA & BHARTI GUPTAProfessor of Organic Chemistry

All rights reserved. No part of this publication may be reproduced, stored in a databaseor retrieval system, or transmitted in any form or by any means, electronic, mechanical,photocopying, recording, or otherwise, without the prior written Permission of the writter.

First Indian Print: September 2015

This edition is manufactured in Indian and is authorized for sale only in India, Bangladesh,Pakistan, Nepal, Sri Lanka & Maldeves.

Printed & Distributed by:Udaan Classes Pvt. Ltd.Rainbow building, Patna &Madhur SatyapushpaShubhash Nagar, Kota9122057123

Price: Rs. 300/-

Copyright © 2015 by Ajnish Gupta

PrefaceThe guiding principle in writing this book was to create a textbook for students- a text-book that presents the material in a way that they learn to solve all the questions ofprevious year board questions by themself at appropriate space. This spacing area helpthe students to think for the length of the answer which they have to write.As the school examination plays the most important role in the life of Student and theirmarks are counted in many espect of life and from todays scenario, the importance ofschool examination is maximise by government as fixed weightage of theseexaminations are counted in the process of admission to any engineering or higher leveleducational programme. Now one question arises, what should be the way to study toget maximum percentage. The answer is so simple and we know it well. We should planour way of studies in such a way that along with the school studies we should also keepan eye on what types of questions are being asked in the real examination.We had prepared this workbook in chapterwise manner which are further divided intotopics, in the same way in which we taught in our classroom so that you should feeleasy to understand & practice correctly. For better picture of the topic, the questions ineach topic have been arranged as per their marks and in ascending order i.e. 2011-2015i.e. 1 marks questions, 2 Marks questions, 3 Marks questions & 5 Marks questions.We had tried our best to answer all the questions according to CBSE marking scheme sothat student can learn correct way to get more marks in exam. So this book will surelyhelp you to get a high success in 12th class board examination.However we had put our best efforts in preparing this book, but if any error or what soever has been skipped out, we will by heart welcome your suggestion. We would like tothank the editors and production staff for their efforts in bringing out the book.Suggestions from readers for the improvement of the book are welcome.

Ajnish Kumar Gupta & Bharti [email protected]

9122057123

mailto:[email protected]

AcknowledgementWe are thankful to all the teachers who taught us during the concept building session ofour life specially Dr. Nizamuddin sir, senior Chandra Vijay Rao and Dr. Vijay PratimaMittal madam.We have written this book to remove the fever of organic chemistry from mind ofstudents.We particularly want to thank many wonderful and talented students whom we havetaught over the years who in turn taught us how to be a good teacher and how we canhelp others.We want to make this book as user friendly as possible, and we will appreciate anycomments that will help us to achieve this goal in future editions.Finally, this edition has been presented before you with efforts to make it error free. Anythat remain are our responsibility; if you find any, please let us know so they can becorrected in future printing.

Ajnish Gupta & Bharti GuptaProfessors of Organic [email protected]

09122057123

mailto:[email protected]

Table of ContentsChapter Title Page

1. Haloalkanes and Haloarenes :1 Mark Questions 1-42 Marks Questions 4-83 Marks Question 8-14

2. Alcohols, Phenols and Ethers :1 Mark Questions 15-17 & 232 Marks Questions 17-20 & 233 Marks Question 21-22 & 24-25

3. Aldehydes, Ketones and Carboxylic Acids :1 Mark Questions 26-30 & 39-402 Marks Questions 30-31 & 40-423 Marks Question 32-34 & 42-435 Marks Questions 34-38 & 44-50

4. Organic Compounds containing Nitrogen :1 Mark Questions 51-542 Marks Questions 54-573 Marks Question 57-66

5. Biomolecules :1 Mark Questions 67-68 & 71-732 Marks Questions 68-69 & 73-743 Marks Question 69-71 & 75-77

6. Polymers :1 Mark Questions 78-792 Marks Questions 79-813 Marks Question 81-85

7. Chemistry in Everyday Life :1 Mark Questions 86-872 Marks Questions 87-883 Marks Question 89-93

8. Answers : 94-159

DedicationDedicated to all those students who are in fever of OrganicChemistry.

Unit I Solid StateUnit II SolutionsUnit III ElectrochemistryUnit IV Chemical KineticsUnit V Surface ChemistryUnit VI General Principles and Processes of Isolation of ElementsUnit VII p -Block ElementsUnit VIII d -and f -Block ElementsUnit IX Coordination CompoundsUnit X Haloalkanes and HaloarenesUnit XI Alcohols, Phenols and EthersUnit XII Aldehydes, Ketones and Carboxylic AcidsUnit XIII Organic Compounds containing NitrogenUnit XIV BiomoleculesUnit XV PolymersUnit XVI Chemistry in Everyday Life

Theory : Chapters Marks

Org

anic

Inor

gani

cPh

ysic

al

23

19

28

Total Marks : 70

Volumetric AnalysisSalt AnalysisContent Based ExperimentProject WorkClass Record and Viva

0808060404

Practical : MarksEvaluation Scheme

Total Marks : 30

Marking Scheme in Board Examinations

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1Organic Chemistry is easy...

Haloalkanes and Haloarenes

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1 Mark Questions:1. Write the IUPAC name of the following compound: 3 3 2(CH ) CCH Br . [Delhi 2011]

_______________________________________________________________________________________________________________________________________________________________________________________________________________________________________

2. Write the IUPAC name of the following compound: 2 2CH =CHCH Br. [All India 2011]

_______________________________________________________________________________________________________________________________________________________________________________________________________________________________________

3. Draw the structure of 1,4-Dibromobut-2-ene. [Delhi 2011]_______________________________________________________________________________________________________________________________________________________________________________________________________________________________________

4. Draw the structure of 2-(2-Bromophenyl)butane. [Delhi 2011]_______________________________________________________________________________________________________________________________________________________________________________________________________________________________________

5. Draw the structure of 2-(2-Chlorophenyl)-1-iodooctane. [All India 2011]_______________________________________________________________________________________________________________________________________________________________________________________________________________________________________

6. Draw the structure of the following compound: 1-bromo-4-sec-butyl-2-methylbenzene.[All India 2011]

_______________________________________________________________________________________________________________________________________________________________________________________________________________________________________

Chapter

01Haloalkanes and Haloarenes

Organic Chemistry is easy...2


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7. Draw the structure of the following organic compound: 2-Chloro-3-methylpentane[All India 2011]

_______________________________________________________________________________________________________________________________________________________________________________________________________________________________________

8. Which will react faster in SN2 displacement: 1-Bromopentane or 2-Bromopentane and why?[Foreign 2011]

_______________________________________________________________________________________________________________________________________________________________________________________________________________________________________

9. Draw the structure of the following compound: 1-(4-Chlorophenyl)-2-methylpropane[Delhi 2011]

_______________________________________________________________________________________________________________________________________________________________________________________________________________________________________

10. Give the IUPAC name of the following compound: 2 2CH =C–CH Br

3CH[Delhi 2012]

_______________________________________________________________________________________________________________________________________________________________________________________________________________________________________

11. What happens when bromine attacks over 2 2CH =CH–CH –C CH? [All India 2012]

_______________________________________________________________________________________________________________________________________________________________________________________________________________________________________

12. Write the IUPAC name of 3 2 3(CH ) CH.CH(Cl)CH [Delhi 2013]

_______________________________________________________________________________________________________________________________________________________________________________________________________________________________________

13. Write the IUPAC name of 3 2 2CH – CH –CH –CH=CHCl

[Delhi 2013]

_______________________________________________________________________________________________________________________________________________________________________________________________________________________________________

14. What happens when CH3–Br is treated with KCN? [Delhi 2013]_______________________________________________________________________________________________________________________________________________________________________________________________________________________________________



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15. What happens when Ethyl chloride is treated with aqueous KOH? [Delhi 2013]_______________________________________________________________________________________________________________________________________________________________________________________________________________________________________

16. Write the IUPAC name of 3 3CH CH=CH–C–CHBr

3CH

[Delhi 2013]

_______________________________________________________________________________________________________________________________________________________________________________________________________________________________________

17. Which compound in the following pair undergoes faster towards SN1 reaction?

(i) Cl

(ii) Cl

[Delhi 2013]

_______________________________________________________________________________________________________________________________________________________________________________________________________________________________________

18. Write the IUPAC name of the following compound: 3 3CH –C – CH–CH3CH

Cl3CH[All India 2013]

_______________________________________________________________________________________________________________________________________________________________________________________________________________________________________

19. Write the IUPAC name of the following compound:

Cl

Cl3CH [All India 2013]

_______________________________________________________________________________________________________________________________________________________________________________________________________________________________________

20. Write the IUPAC name of the following compound: 3 2 3CH –CH–CH –CH–CHBr Cl

[All India 2013]

_______________________________________________________________________________________________________________________________________________________________________________________________________________________________________

21. How Methylbromide be preferentially converted to methyl isocyanide? [Delhi 2013]_______________________________________________________________________________________________________________________________________________________________________________________________________________________________________



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22. Identify the chiral molecule in the following pair: Cl Cl [Delhi 2014]

_______________________________________________________________________________________________________________________________________________________________________________________________________________________________________

23. Draw the structure of 2-Bromopentane: [Delhi 2014]____________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________

24. Which would undergo SN2 reaction faster in the following pair and why?

3 2 3 3CH –CH –Br and CH –C–CH3CH

Br[Delhi 2015]

____________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________

25. Which would undergo SN1 reaction faster in the following pair?

3 2 2 3 3CH –CH –CH –Br and CH –CH–CH

Br[All India 2015]

____________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________

2 Marks Questions:26. Explain why

(i) alkyl halides, though polar, are immiscible with water?(ii) Grignard’s reagent should be prepared under anhydrous conditions? [Foreign 2012]___________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________



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27. Account for the following:(i) The C–Cl bond length in chlorobenzene is shorter than that in CH3–Cl.(ii) Chloroform is stored in closed dark brown bottles. [Delhi 2013]__________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________

28. Chlorobenzene is extremely less reactive towards a nucleophilic substitution reaction. Give tworeasons for the same. [Delhi 2013]__________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________

29. Write the mechanism of the following reaction:

3 2 3 2 2HBrCH CH OH CH CH Br + H O [Delhi 2014]

__________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________



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30. (i) Which alkyl halide from the following pair is chiral and undergoes faster SN2 reactions?

(a) Br (b) Br

(ii) Out of SN1 and SN2, which reaction occurs with(a) inversion of configuration? (b) racemisation? [All India 2014]

________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________

31. Draw the structure of major monohalo product in each of the following reactions:

(i) 2SOClOH (ii) 2 2CH –CH=CH + HBr Peroxide

[All India 2014]________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________

32. Write chemical equations when(i) Ethylchloride is treated with aqueous KOH.(ii) Chlorobenzene is treated with CH3COCl in the presence of anhydrous AlCl3.[Foreign 2014]_____________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________



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33. (i) Which alkyl halide from the following pairs would you expect to react more rapidly by anSN2 mechanism and why?

3 2 3CH –CH –CH–CHBr

3 2 2 2CH –CH –CH –CH –Br

(ii) Racemisation occurs in SN1 reactions. Why? [Foreign 2014]__________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________

34. Write the structures of the following organic halogen compounds:(i) p-Bromochlorobenzene (ii) 1-Chloro-4-ethylcyclohexane

[All India 2014]___________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________

35. What are ambident nucleophiles? Explain with an example. [All India 2014]_______________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________



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36. Draw the structures of the following organic halogen compounds:(i) 4-Tert-butyl-3-iodoheptane (ii) 4-Bromo-3-methylpent-2-ene

[All India 2014_____________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________

37. Write the IUPAC names of the following compounds:(i) CH2 = CHCH2Br (ii) (CCl3)3CCl [All India 2014]________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________

3 Marks Questions:38. Answer the following:

(i) Haloalkanes easily dissolve in organic solvents than haloarene. Why?(ii) What is known as racemic mixture? Give an example.(iii) Of the two bromo derivatives, C6H5CH(CH3)Br and (C6H5)CH(C6H5)Br, which one is more

reactive in SN1 substitution reaction and why? [Delhi 2011]__________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________



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39. Rearrange the compounds of each of the following sets in order of reactivity towards SN2displacement.(i) 2-Bromo-2-methylbutane, 1-Bromopentane, 2-Bromopentane.(ii) 1-Bromo-3-methylbutane, 2-Bromo-2-methylbutane, 3-Bromo-2-methylbutane.(iii) 1-Bromobutane, 1-Bromo-2, 2-Dimethylpropane, 1-Bromo-2-methylbutane,

1-Bromo-3-methylbutane. [All India 2011]________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________

40. (i) Write a chemical test to distinguish between:(a) Chlorobenzene and Benzyl chloride. (b) Chloroform and Carbontetrachloride.

(ii) Why is Methylchloride hydrolysed more easily than Chlorobenzene? [All India 2011]_____________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________

41. Complete the following reactions:

H

HH

+ HBr[Foreign 2011]

________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________



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42. Although chlorine is an electron withdrawing group, yet it is ortho, para-directing inelectrophilic aromatic substitution reactions. Explain, why is it so? [Delhi 2012]______________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________

43. Answer the following questions:(i) What is meant by chirality of a compound? Give an example.(ii) Which one of the following compounds is more easily hydrolysed by KOH and why?

3 2 3CH CHClCH CH or 3 2 2 2CH CH CH CH Cl [All India 2012]

_____________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________



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44. Give reasons for the following:(i) Ethyl iodide undergoes SN2 reaction faster than ethyl bromide.

(ii) ( ) 2-butanol is optically inactive.

(iii) C–X bond length in halobenzene is smaller than C–X bond length in CH3–X.[All India 2013]_____________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________

45. Explain the following:The dipole moment of Chlorobenzene is lower than that of Cyclohexylchloride. [Delhi 2013]______________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________



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46. (i) Draw the structures of major monohalo products in each of the following reactions:

(a) 2CH OH 5PCl (b) 2 2CH –CH=CH + HBr

(ii) Which halogen compound in each of the following pairs will react faster in SN2 reaction?

(a) 3 3CH Br or CH I (b) 3 3 3(CH ) C–Cl or CH –Cl [Delhi 2014]

________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________

47. Write the product of the following reactions:

(a) 3CH –Cl + KCN ? (b)3+ CH –Cl 3Anhyd. AlCl

Cl? + ?

[Delhi 2014]____________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________



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48. Give reasons:(i) n-Butyl bromide has higher boiling point than t-Butyl bromide.(ii) Racemic mixture is optically inactive.(iii) The presence of nitro group (–NO2) at o/p positions increases the reactivity of haloarenes

towards nucleophilic substitution reactions. [Delhi 2015]_____________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________



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49. How can the following conversions be carried out?(i) Aniline to Bromobenzene (ii) Chlorobenzene to 2-Chloroacetophenone(iii) Chloroethane to Butane

OrWhat happens when

(i) Chlorobenzene is treated with Cl2/FeCl3? (ii) Ethyl chloride is treated with AgNO2?(iii) 2-Bromopentane is treated with alcoholic KOH?

Write the chemical equations in support of your answer. [All India 2015]____________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________

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