Download CHE-05 year 2004

CHE-05
Assignment Booklet
Bachelor's Degree Programme (B.Sc.)
Organic Chemistry
CHE-05
School of Sciences
Indira Gandhi National Open University
New Delhi-110 068
2004
Dear Students,
As explained in the programme guide for B.Sc. Programme, you have to do 2 Assignments for this elective
courses in Organic Chemistry. Both of these Assignments are Tutor Marked (TMAs).
The blockwise distribution of assignments is as follows:
Assignment-01 (TMA) –
Assignment-02 (TMA) –
(Blocks 1 and 2)
(Blocks 3 and 4)
Instructions for Formating Your Assignments
Before attempting the assignments, please read the following instructions carefully.
1. On top of the first page of each TMA answer sheet, please write the details exactly in the following
format:
Enrolment No : .........................……………
Name
: ........................…………….
Address
: ........................…………….
Course Code : ........................……………
…...………………………..
Course Title
…………………………….
: .......................…………….
Assignment No : ......................…………….
Study Centre : ...........................................
Date
: ………...........................…..
PLEASE FOLLOW THE ABOVE FORMAT STRICTLY TO FACILITATE EVALUATION AND
TO AVOID DELAY.
2. Use only foolscap size writing paper of good quality (but not of very thin variety) for writing your
answers.
3. Leave 4 cm margin on the left, top and bottom of your answer sheet.
4. Your answers should be precise.
5. While solving problems, clearly indicate the question number along with the part being solved.
6. Assignment is to be submitted as per the dates mentioned below.
Answer sheets received after the due date shall not be accepted.
We strongly suggest that you should retain a copy of your assignment.
Wishing you all good luck.
Assignment Nos.
Date of submission
Where to send
Assignment-01 (TMA)
30-06-2004
The Co-ordinator of your study centre
Assignment-02 (TMA)
30-10-2004
The Co-ordinator of your study centre
2
Assignment - 01
(Tutor Marked Assignment)
ORGANIC CHEMISTRY
Elective Course in Chemistry
Course Code: CHE-05
Assignment Code: CHE-05/TMA-01/2004
Maximum Marks: 100
Answer all questions.
1.
a)
Give the IUPAC names of the following compounds:
Br
i)
(6)
(CH3)3CCHCH3
O
b)
2.
a)
ii)
HOCH2CH2CCH3
iii)
CH3CH = CHCHCH3
Cl
Write the structures of the following compounds:
i)
Methyl propenoate
ii)
2-phenylbutanamide
Assign the configuration as E or Z to the following compounds:
B
Cl
i)
F
CH3OC
ii)
ClH2C
4.
(5)
C = C
I
3.
(4)
COCH2Cl
C = C
Cl
b)
Write all possible stereoisomers of 2, 3, 4-trihydroxybutanol and classify them as
enantiomers or diastereomers.
(5)
a)
What is a racemic mixture? How does it differ from a meso compound? Briefly
discuss one method of resolution of a racemic mixture.
(5)
b)
Draw various conformations of butane and arrange them in the decreasing order
of their energy.
(5)
a)
Explain the following terms:
i)
Chemical exchange
ii)
Resonance
iii)
Bathochromic shift
(6)
3
5.
6.
b)
Give reasons why
i)
in a homologous series, the melting point increases with the increase in
molecular weight?
ii)
are some molecules IR active while others are not?
(4)
a)
Why is ethanoic acid more acidic the ethanol?
(3)
b)
What is tautomerism? Give two examples.
(3)
c)
Write the expression for the acidity constant. Name atleast two factors which
affect the strength of an acid and briefly discuss any one of them.
(4)
a)
How would you prepare alkanes using sodium. What are the advantages and
disadvantages of this method.
(2)
b)
Give the names of the hydrocarbons with the following approximate composition:
i)
C1 – C4
ii)
C5 – C7
iii)
C8 – C11
iv)
C13 – C18
v)
C16 – C20
vi)
C20 – C30
(3)
c)
Fill in the blanks:
(3)
i)
The boiling point of alkanes increase with the ______________ in the
number of carbon atoms.
ii)
Alkanes are soluble in _______________ solvents.
iii)
The NMR signal for terminal protons (CH3) of alkanes appears at  _________.
d)
Complete the following reactions:
Zn /Hg
HCl

 ………………………………
i)
ii)
7.
a)
(2)
CuO.Cr O
2 3

CH3CH2COOH + C2H5N
………………………..
Suggest the structure of the alkene/diene that give the following products:
i)
…………………..
H2 /Pd


(5)
2-Methylhexane
CH2  CH2
ii)
…………………..

 Cyclohexene
iii)
…………………..
3 2

2. H O , OH
1. (BH )
Cyclohexanol
2 2
iv)
v)
b)
…………………..
…………………..
Br2

1,4-Dibromo-2-butene
Ph3P  CH2

 Butene
Discuss the structure of diene briefly.
(5)
4
8.
a)
Complete the following statements:
i)
When both the halogen atoms are present on the same carbon atom, the
compound is known as a ________________ dihalide.
ii)
The internal alkynes have no NMR absorption characteristic of an alkynyl
hydrogen because they have ______________ alkynyl hydrogen.
iii)
The alkynes are non-polar and dissolve in a ________________ solvent.
(3)
b)
Starting with acetylene and suitable alkyl halide, how would you synthesise the
following compounds?
i)
Decane
ii)
Hexanal
(4)
c)
Complete the following reactions:
(3)

i)
9.
10.


Nichrome
ii)
HOCH2-CH2CH2CH2-OH
iii)
CH3CH2-CH2BH3

H 

CH COOH
3



……………………….
…………………………
a)
What is resonance energy? Explain with the help of an example.
(2)
b)
What do you understand by activating and deactivating groups?
(2)
c)
Write the resonance structures of a cations formed from nitrobenzene during its
i)
ortho-nitration
ii)
meta-nitration
iii)
para-nitration
(3)
d)
Complete the following reactions:
(3)
a)
hυ 


……………………
i)
+ Cl2
ii)
[O]


iii)
CH3COOH/Cr2O3



…………………..
……………………
Give the IUPAC names of the following compounds:
i)
5
(3)
ii)
iii)
b)
Explain the following facts:
i)
Pyrrole in less basic than pyridine.
ii)
The reactivity of pyridine towards nucleophilic substitution is very high.
(2)
c)
Draw the orbital picture of pyridine.
(2)
d)
Complete the following reactions:
(3)
i)
ii)
iii)


…………………
Zn/CH3COOH


….……………...
2CH3CHO + HCHO + NH3
+


6
….………………
Assignment - 02
(Tutor Marked Assignment)
ORGANIC CHEMISTRY
Elective Course in Chemistry
Course Code: CHE-05
Assignment Code: CHE-05/TMA-02/2004
Maximum Marks: 100
Answer all questions.
1.
2.
3.
a)
Define SN1 and SN2 reaction and discuss their mechanism and stereochemistry.
b)
Complete the following reactions:
(5)
(51)
CuCl 2
i)
C6H6 + HCl + ½O2 

ii)
4
2
2C6H5Cl + CCl3CHO 

iii)
C6H5Cl + 2NaOH
iv)
C6H5ONa + CO2
v)
CH3CH2CHBrCH3
H SO
473K
   
Pressure,CuSO 4
323K


NaOC H 5
 2
C 2 H 5 OH, 
a)
How will you distinguish primary, secondary and tertiary alcohols by a simple
chemical test.
(2)
b)
Write the catalytic dehydrogenation products of primary, secondary and tertiary
alcohols.
(3)
c)
How will you carry out the following conversions?
i)
Chlorobenzene to phenol
ii)
Solidaldity to 1,2-benzenediol (
)
a)
What is aldol condensation? Discuss its mechanism.
(5)
b)
Complete the following reactions:
(5)
i)
373K

CH33CH3 + H2O2 

ii)
3
C6H5 + HCN + HCl 
(22½)
H
(i) AlCl
(ii) H O
2
O
iii)
Zn(Hg)HCl

CH3CCH3  
iv)
CH3NH2 + CHCl3 + KOH

O
v)
4.
Tollen's reagent
CH3CH 
a)
Write a short note on crown ethers.
(5)
b)
Discuss the chemistry of haloform reaction.
(5)
7
5.
Write chemical equations for following named reactions
a)
Mannich reaction
b)
Willgerolt reaction
c)
Benzoin condensation
d)
Knoevengel reaction
e)
Perkin reaction
f)
Baezer-Villiger oxidation
g)
Wittig reaction
h)
Schotten-Backmann reaction
i)
Reimer-Tiemann reaction
j)
Cannizzaro reaction
8
(110)