ST. JOSEPH S COLLEGE OF ARTS & SCIENCE (AUTONOMOUS) ST. JOSEPH S COLLEGE ROAD, CUDDALORE CH509S ORGANIC CHEMISTRY III (SEMESTER-V)

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1 UNIT I 1. Among the following, the strongest base is: 2. Which of the statement about the two structures is correct? a) II is not an acceptable cannonical structure because the carbonium ions are less stable than ammonium ion b) II is not an acceptable structure because N-atom has 10 valence electrons. c) II is not an acceptable structure because it is non aromatic d) II is an acceptable cannonical structure. 3. Diazo coupling reaction is reaction 4. In reaction benzene diazonium chloride is converted into biphenyl. 5. Nitro-acinitro tautomerism is not exhibited by a) Nitrobenzene b) Nitromethane c) Nitroethane d) Nitropropane 6. N-methylaniline is an example of a) 1 amine b) 2 amine c) 3 amine d) None of the above 7. The correct order of basicity of amines a. Aniline > o-nitro aniline > m-nitro aniline > p-nitro aniline b. Aniline > m-nitro aniline> p-nitro aniline> o-nitro aniline c. m-nitro aniline> p-nitro aniline> o-nitro aniline>aniline d. p-nitro aniline> o-nitro aniline> m-nitro aniline>aniline 8. Formation of biphenyl from benzene dizaniam chlosude is reaction. a) Gomberg reaction b) Coupling reaction c) Sandmeyer reaction d) Gatterman reaction 9. Nitrobenzene on reduction in neutral medium gives. 10. Which reaction sequence would be the best to prepare 3-chloro aniline from benzene? a. Chlorination, nitration and reduction b. Nitration, reduction and chlorination c. Nitration, chlorination and reduction d. Nitration, reduction,acylaton,chlorination and hydrolysis 11. CuCl is used in, a. Sandmeyer reaction b. Benzilic acid rearrangement c. Curtius rearrangement d. Claisen rearrangement 12. Biaryls are prepared by

2 a. Gomberg reaction b. Lossen rearrangement c. Schmidt reaction d. Bayer-Villiger rearrangement 13. Cuprous chloride is used in reaction. a) Gomberg b) Gattermann c) Sandmeyer d) Coupling 14. Nitro benzene on reaction with Sn/HCl gives The electrolytic reduction of nitrobenzene in strongly acidic medium produces 1. Convert benzene to 3-nitroaniline. Show the proper steps 2. Write the reaction conditions for coupling reactions involving benzene diazonium chloride. 3. What is a Gomberg reaction? Give the reaction. 4. All chloro anilines are less basic than aniline -Explain this fact 5. Write Sandmeyer reaction. 6. Give electrolytic reduction of ritrobenzene 7. Write Ritter reaction for the preparation of primaryamines 8. Predict the product and suggest a suitable mechanism for the following reaction. 9. Which is more basic among Benzoic acid and p-nitro benzoic acid? Give the reason. 10. Suggest a suitable method for preparing o-dinitrobenzene from o-nitroaniline. 11. How are tertiary amines prepared? 12. Convert benzene to 4- bromonitrobenzene. Show the proper steps. 13. Explain coupling reaction. 14. Discuss the basicity of amines. 1. With the help of resonance structures, show the effect of a)+i groups and b)-i groups on the coupling reactions of diazonium chloride. 2. Convert m-nitroaniline to m-chloroiodo benzene. 3. Write any three nucleophilic substitution reactions of aromatic nitro compounds. 4. Give reduction reaction of nitrocompounds in acid and neutral medium. 5. Predict the product and give the mechanism. 6. Suggest a method to prepare 1,3,5-trinitrobenzene from toluene. 7. Explain Gomberg reaction with an example.

3 UNIT II 1. The optically active isomer of tartaric acid is named as D-(+) tartaric acid because it has a positive: a) Optical rotation and is derived from D-(-) glucose. b) ph value in organic solvent c) Optical rotation and is derived from D-(+)-glucose. d) Optical rotation when substituted by deuterium. 2. The correct statement about the following structures: a) A and B are identical b) A and B are diastereomers c) A and B are enantiomers d) A and C are enantiomers 3. Tautomers are: a) Geometrical isomers b) Structural isomers c) Enantiomers d) Diastereo isomer 4. Resolution of racemic tartaric acid is carried out by using a) (-)- cinchonine b) (+)-aspargine c) (-)-aspargine d) (+)-cinchonine 5. Compound(s) that show optical activity a) Allenes b) Spiranes c) Biphenyl d) All of the above 6. Glucose is an epimer of. 7. Nitro-acinitro tautomerism is not achieved by nitro compounds. 8. Which of the symmetry elements is present in the meso-tartaic acid? a. Centre of symmetry b. Proper axis of symmetry c. Plane of symmetry d. Improper axis of symmetry 9. The mechanism of Walden Inversion is a) SN2 b) SN1 c) SN i d) E2 10. In erythro form the same type of groups are on side. a) Opposite b) Left c) Right d) Same 11. The d-form of tartaric acid is represented as The configurational isomers which are not enantiomers are called 1. What is an epimer? Give an example. 2. What is Walden inversion? Give example. 3. What is a diastereomer? Explain with an example. 4. What is optical activity? 5. What is asymmetric synthesis? 6. Write the structure of mesotartaric acid in Newmann projection and translate it into Fischer projection. 7. Assign R / S configuration to the chiral center in each molecule.

4 8. Give the mechanism of racemization. 9. Discuss the optically activity of biphenyls. 10. What is tautomerism? 11. Write fisher projection formula for S-glyceric acid 12. Draw the Fischer projection formula of threo-2,3-dibromopentane 1. a) What is a meso compound? Give example. b) What is racemic modification? With example, Show the methods of racemization. c) Using an example, differentiate threo and erythro enantiomers. 2. a) Explain plane of symmetry with an example. b) Discuss CIP rules for predicting R and S configuration 3. Explain the optical activity in allenes. 4. a) What is a meso compound? Give example. b) What is racemic modification? With example, Show the methods of racemization. c) Using an example, differentiate threo and erythro enantiomers. 5. a) What is asymmetric synthesis? b) How do you synthesis (-)-lactic acid from pyruvic acid? c) Draw the structure of (2s,3R)-3-chloro 2-pentanol. Explain the optical activity of this molecule. UNIT III 1. The incorrect statement regarding the acetoacetic ester as a synthetic tool is based on: a) The acidity of the methylene hydrogen in it b) The ability of the ester to undergo a hydrolysis c) The ability of the attacking nucleophile to remove an acidic proton d) The formation of a resonance stabilized anion 2. Tautomers are: a) Geometrical isomers b) Structural isomers c) Enantiomers d) Diastereo isomer 3. The reaction of a ketone with acetoacetic ester yields α,β- Unsaturated acids. This is called as. 4. No of active hydrogens present in malanic ester is a) 1 b) 2 c) 3 d) 4 5. Diazomethane has structure. a) Diazirin ring b) Linear c) Trigonal d) Tetrahechal 6. Nitro-acinitro tautomerism is not achieved by nitro compounds. 7. Acetoacetic ester condenses with aldehydes or ketones in the presence of a base and the products in acid hydrolysis yields

5 a. Saturated fatty acids b. ketonic acids c. Dibasic acids d. α, β-unsatrated acids 8. Which of the following pairs exhibit tautomerism? a. Propanol and propanone b. 1-propanol and 1- propanone c. Ethanol and vinyl alcohol d. Vinyl alcohol and ethanol 9. When acetoacetic ester is subjected to ketonic hydrolysis, the ketone obtained is. 10. Compound NOT having active methylene group is a) Cyano acetic ester b) Aceto acetic ester c) Lactic acid d) Ethyl aceto acetate 11. Methyl ester can be obtained using a) Diazomethane b) Ethanol c) Methyl acetate d) Malonic acid. 12. The structure of diethyl malonate is What is acidic hydrolysis of acetoacetic ester? Give an example 2. Define carbonyl polarization. 3. What is keto-enol tautomerism? 4. Give any two synthetic uses of malonic ester. 5. Write the resonance structures is diazomethare. 6. What is tautomerism? 7. Give any two compounds having alpha hydrogen and highlight their reactivity. 8. Give any one preparation of diazomethane. 1. a) What is an active methylene group? b) Convert acetoacetic ester to cinnamic acid. c) How will you prepare antipyrine from acetoacetic ester? 2. Explain the preparation and properties of diazoacetic ester. 3. a) Complete the following reaction. 4. a) Starting from diethyl malonate how will you synthesize Propanoic acid. b) Give any two applications of Diazomethane. c) Discuss the mechanism of keto-enol tautomerism.

6 UNIT IV 1. Keto-enol tautomerism takes place in the following rearrangement a) Hoffmann b) Claisen c) Cope d) Curtius 2. Almost without exception, it has been found in Beckmann rearrangement that it always the group that is the OH group that migrates. 3. Backmann rearrangement occurs in the presence of reagents, a) Basic b) Neutral c) Free radical d) Acidic 4. An example of 1,2-shift in rearrangement reactions is a) Curtius rearrangement b) Backmann rearrangement c) Coupling reaction d) None 5. The catalyst used is Bayer-villiger rearrangement is 6. Dienane intermediate is formed is rearrangement. a) Claisen b) Cope c) Pinacol-pinacolane d) Beckmann 7. An example for intramolecular rearrangementis a) Hofmann b) Pinacol-Pinacolone c) Claisen d) All of the above 8. The convension of ketoximes to N-substituted amides is rearrangemeat. 9. The intermediate in Hoffmann rearrangement is a. [RCONHBr] b. [RCONBr -] c. [RNCO] d. All of these 10. When O-acyl derivatives of hydroxamic acid gives isocyanates in the presence of a base. This reaction is known as, a. Curtius rearrangement b. Lossen rearrangement c. Schmidt reaction d. Bayer-Villiger rearrangement 11. is used as catalyst in Beckmann rearrangement. 12. The substrate used in Beckmann rearrangement is a) Ester b) Acid c) Amine d) Ketoxime 13. Bromine and NaOH are used in the following rearrangement: a) Hofmann b) Beckmann c) Curtius d) Benzilic acid 14. The conversion of allyl phenyl ether to o-allyl phenol is called rearrangement 1. What is Bayer-villiger rearrangement? Give an example. 2. What is Pinacol-pinacolone rearrangement? 3. Define molecular rearrangemeat. 4. Give the mechanism for the following reaction. 5. Explain briefly Claisen rearrangement. 6. Give evidence for carbonium ion intermediate. 7. Illustrate Oxy Cope rearrangement with an example.

7 1. a) What is Curtius rearrangement? b) Explain the Fries rearrangement? c) Complete the following reaction with proper mechanism: 2. Explain the mechanism of Baeyer-Villiger rearrangement. 3. Explain the mechanism of Beckmann rearrangement. 4. Give the mechanism for the following reaction 5. Illustrate the formation amine from amide. 6. Give the mechanism of Pinacol-pinacolone rearrangement. 7. Give the mechanism of Benzilic acid rearrangement UNIT V 1. Glucose reacts with acetic anhydride to form 3- a) Monoacetate b) Tetraacetate c) Pentaacetate d) Hexaacetate 2. Which of the following is not an amino acid a) Glycine b) Alanine c) Histidine d) Benzidine 3. The helical structure of proteins is stabilized by. 4. An example for polysaccharide is a) Starch b) Sucrose c) Lactose d) Maltose 5. Gun cotton is a) Cellulose b) Cellulose mono nitrate c) Cellulose tri nitrate d) Cellulose dinitrate 6. Glucose is an epimer of. 7. An example for acidic amino acid a) Glycine b) Aspastic acid c) Alanine d) Phenylalanine 8. Cellulose is soluble only is 9. The molecular formula for starch is. 10. At its isoelectric points aminoacid has the solubility. 11. Arabinose is a) Aldohexose b) Aldopentose c) Ketopentose d) Ketohexose 12. Which among the following is an optically inactive amino acid? a) Glycine b) Glutamic acid c) Alanine d) Aspartic acid 1. Give the Erlenmeyer synthesis for amino acids.

8 2. How is fructose converted to osazone? 3. What is epimerization? 4. Write Strecker synthesis for amino acid. 5. Give the classtication of aminoacids. 6. What is isoelectric point? 7. How is osazone formed? 8. Give the Erlenmeyer synthesis for amino acids. 9. What is Sanger s reagent? Write one of its applications. 10. How will you convert cyclohexanone to cycloheptanone? 1. How is a peptide synthesized using Merrifield Resin? Explain the steps involved in this process. 2. Explain primary structure of proteins? 3. i) Write pyranose forms of glucose and fructose. ii) Give any four properties of stanch. 4. i) Convert aldose into ketose ii) Convert aldopentose into aldohexose. 5. a) How do you prepare D-glucose from D-arabinose? b) Convert glycine into phenylalanine. 6. Give Haworth projection formula of glucose. 7. a) Give the structure of maltose. b) What is end group analysis? c) How will you synthesize a tripeptide?

Exam 1 (Monday, July 6, 2015)

Exam 1 (Monday, July 6, 2015) Chem 231 Summer 2015 Assigned Homework Problems Last updated: Friday, July 24, 2015 Problems Assigned from Essential Organic Chemistry, 2 nd Edition, Paula Yurkanis Bruice, Prentice Hall, New York, NY,