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·1 CHE-051
BACHELOR OF SCIENCE (B.Se.)
Term-End Examination
June, 2016

00577
CHEMISTRY CHE-05 ORGANIC CHEMISTRY
Time Jwurs Maximum Marks: 50
Note: Answer all the four questions.

1. Attempt all parts Give the IUPAC names of any two of the following compounds: 2x1=2 <img src='./qimages/11879-1ai.jpg'>

(ii) <img src='./qimages/11879-1aii.jpg'>

(iii) CH3COOCH2CH3
Write the structural formula of anyone of the following compounds: 1
2,3,5-Trimethyl-2-hexene

(ii) 3-Chloro-2-methylpentane Assign E or Z configuration to any one of the following compounds: 1. <img src='./qimages/11879-1ci.jpg'>

(ii) <img src='./qimages/11879-1cii.jpg'> Assign RIB configuration to anyone of the following compounds: <img src='./qimages/11879-1di.jpg'>

(ii) <img src='./qimages/11879-1dii.jpg'>

2. Attempt any five of the following: 5x2=10 Which of the following is a stronger acid and why? C6H5COOH

(ii) CH3COOH Explain why p-hydroxybenzaldehyde has a higher boiling point than o-hydroxybenzaldehyde. Which of the following compounds will absorb uv radiation of longer wavelength Explain. <img src='./qimages/11879-2ci.jpg'>

(ii) <img src='./qimages/11879-2cii.jpg'> An aromatic hydrocarbon (C8H10) gives benzoic acid on oxidation with alkaline KMnO4. What is its structure? Explain the term transesterification with a suitable example. What are the products obtained when nitrobenzene is reduced with Zn and aq. NH4Cl and Zn and HCl Explain mutarotation with the help of a suitable example.

3. Attempt any five of the following: 5x3=15 Classify the following compounds as aromatic or non-aromatic: <img src='./qimages/11879-3ai.jpg'> <img src='./qimages/11879-3aii.jpg'> <img src='./qimages/3aiii.jpg'> <br>

Also give reason(s) in support of your answer.
Why are all the carbon-carbon bonds in naphthalene not equal in length? How is lactic acid obtained from propanoic acid Write the structure of the product obtained by the action of heat on lactic acid. Arrange the following in the increasing order of reactivity towards nucleophiles and give reason: <img src='./qimages/11879-3di.jpg'> <img src='./qimages/11879-3dii.jpg'> CH3COCH3

(e) A tripeptide on reaction with 1-fluoro-2,4-dinitrobenzene gives the DNP derivative of the peptide which on hydrolysis gives the DNP derivative of glycine alanine phenylalanine. The tripeptide on hydrolysis with carboxypeptidase releases alanine first. What is the primary structure of the tripeptide? How is phenol converted to the following? 2,4,6-Tribromophenol

(ii) Salicylaldehyde

(iii) 1,4-Quinone Explain Wurtz reaction with a suitable example. What are its limitations?

4. Attempt any five of the following: 5x4=20 How can you carry out the following conversions? 2-Butyne to ethyl methyl ketone

(ii) Toluene to benzyl chloride

(iii) Acetone to methyl acetate

(iv) Benzoyl chloride to benzaldehyde Complete the following sequence and identify C and <img src='./qimages/11879-4b.jpg'> Explain the steps involved in the Gabriel synthesis of primary amines. Explain Huckel's rule. On the basis of this rule, discuss the aromatic character of the following:
<img src='./qimages/11879-4di.jpg'> <img src='./qimages/11879-4dii.jpg'>
(iii) <img src='./qimages/11879-4diii.jpg'> Explain why under ordinary conditions, aryl and alkenyl halides are less reactive towards nucleophiles.

(ii) phenols are more acidic than alcohols. Fill in the blanks in the following: Dienes are isomeric with .

(ii) and are used for rating of fuels.

(iii) The terminal hydrogen of alkynes is in nature.

(iv) The region of IR spectrum between 675 and 1250 is called region. Give equations for the following reactions Wittig reaction

(ii) Perkin reaction

(iii) Friedel -Crafts acylation

(iv) Kolbe reaction