Indira Gandhi National Open University (IGNOU) 2005 B.Sc Chemistry Organic - - Question Paper
CHE-5
BACHELOR OF SCIENCE (B.Sc.) Term-End Examination June, 2005
CHEMISTRY CHE-5 : ORGANIC CHEMISTRY
Time : 2 hours Maximum Marks : 50
Note : Attempt all the four questions.
1. (a) Give the 1UPAC names of the following
compounds : 1+1
(i) CH3CH2OCH2CH(CH3)2
(ii) CH2 CHCOOH
(b) Complete any three of the following reactions : 1x3
RC s CR' -........ BaS04, Hz (BH3)2 (iv)-CH3 CH = CH2
2. (a) Attempt any two of the following :
2+2
[)) Which one out of 1,3-pentadiene or 1,4-pcntadiene will have absorption maximum on longer wavelength and why ?
(ii) How will you prepare .4-nitrobenzenamine from benzenamine (aniline) ?
(iii) Write the structure of heterocyclic nucleus present in indole alkaloids and quinoline alkaloids.
(b) Attempt any three of the following :
2x3
How will you convert ? ' '
(i) CH2 = CH CH2CICH2 = CH CH3
(iii) CH3 CH - CH2 CH3 CH CH3 OH (iv) CH3C = CCH3 2 CH3COOH
3* Answer any five of the following ;
(a) Arrive at the configuration of any tu?o of the following molecules using CIP rnles ;
Br 'x
(i) /C = C
OH
COOH
(iii) H C OH
HO C H
(b) Name the symmetry elements present in any two of the following molecules :
(ii) = C CT H3c
(c) What do you understand by ring chain and valence tautomerism ? Cite one example of each,
(d) Give the reaction of methyl magnesium bromide with
(i) carbon dioxide
(ii) methyl'cyanide
(e) Write the products of the following reactions :
(i) 1-propanol 73 K, Cu > ?
A
(ii) 2-methylbutanol 573 K, Cu_ >
What is the importance of the above reactions ?
{0 Give the products obtained when the following acids are heated with a mineral add :
(i) 2-hydroxybutanoic add
(ii) 3-hydroxybutanoic acid
(iii) 4-hydroxybutanoic add
(s) Give the expected products of the reaction between ethyl benzoate and the following reagents :
0) aqueous NH3, heat
(ii) LtAlH4 followed by
(iii) excess of CH3MgBr followed by H30+
(h) How can ethylene oxide be converted into (i) ethanal and (ii) ethane-1,2-diot ?
(a) What is the fingerprint region in IR spectroscopy ? Give its utility. What are various mediums used in recording IR spectrum ?
(b) Give the main uses of studying mass spectrum of an organic compound. What are the expected peaks in the mass spectrum of 2,2-dimethylbutane ?
(c) Which member of each of the following pairs would undergo S2 reaction faster ? Explain.
(Attempt any two) :
CH2C1 Cl
(i) or
(ii) CH2 = CHCHCl or CH3CH2CH2a
(iii) (CH3)2CHCH2C1 or (CH3)3CC1
(d)' Write short notes on any two of the following :
(i) Gattermann synthesis
(ii) Wittig reaction
(ill) Cannizzaro reaction
(e) Give two different methods of converting
2-methylpropanoic acid into its methyl ester.
(f) What is saccharin ? How is it manufactured ? Why has its use been discontinued as a sweetening agent ?
(g) What is Hofmann rearrangement ? Explain with suitable example.
(h) What is Reformatsky reaction ? How can
3-methy]-3-hydroxybutanoic acid be prepared from 2-bromoaceUc acid using this region ?
CHE-5 6
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