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Unformatted text preview: x,/ CHEMISTRY HTK ASSIGNMENT 10 Write equations, indicating reagents and reaction conditions to show the reaction of
2-(N-methylamino) propane with the following substances: a) hydroiodic acid b) propanoyl chloride c) benzoic anhydride d) p-toluenesulphonyl chloride 6) excess methyl iodide, followed by moist silver oxide and then heat
f) hydrochloric acid and sodium nitrite Arrange each of the following sets of compounds in order of increasing basicity: a) i) ammonia
iii) l-aminopropane b) i), benzylamine
ii) N—formylbenzylamine (N—benzylformamide)
iii) N-methylbenzylamine c) i) ethylamine
iii) N¥methylaniline Describe the Hinsberg test and explain how it can be used to distinguish among primary,
secondary and tertiary amines. NuNOz / uct (tar mph) A colourless liquid, A, CZHQN reacts immediately with gold acidiﬁed sodium nitrite to fgrin aneutral yellow oi1,..B. Reaction of compound A with acetic anhydride in pyridine forms a
white solid,@ The NMR spectra of C can be summarized as: 6=1.9(s,lH) ; 6=3.5(s,lH) ; 5=7.3(m,1.67H) Determine the structure of A, B and C and explain the chemistry of the reactions occurring. Give a speciﬁc example for each of the following reactions, writing a complete mechanism
in each case. a) The Gabriel Synthesis b) Reductive amination c) The Hofmann degradation
(1) The Hofmann elimination TURN OVER Given the following information, draw structures for the compounds A, B and C in the
scheme below and explain the chemistry of the reactions involved: i) 0.45 g of B is neutralized by 42.0 cm3 of O. 100 mol L‘1 hydrochloric acid solution. ii) The IR of C has a broad absorption between 2500 cm—1 and 3500 cm“.
iii) 0.14 g of C is neutralized by 11.5 cm3 of 0.100 mol L‘1 sodium hydroxide solution. excess MnOf / H30+
A : C7H7Cl -——-—————> B _... __._. > C
NH3 A Using necessary reagents and reaction conditions, explain how the following syntheses
could be carried out: a) an' amide to an amine with one less carbon atom.
b) an amide‘to an amine with the same number of carbon atoms.
c) an amide to an amine with one more carbon atom. Propose suitable reactions, including reagents and reaction conditions, in order to carry out
the following syntheses: a) acetone to isopropylamine b) ethylamine to ethene c) ethane to aminoethane ) CHEW : 0H 1 “WM—"*4 Ll, N (“l-l7 k H, C 11 2 W:
. / d) propene to l-amlnobutane e) propan-l-ol to 2—aminopropane r t) benzene to o-toluidine ii" c“ : (My Using acetic acid as the only organic compound, and using any necessary inorganic
reagents, suggest suitable syntheses for each of the following compounds: a) ethylamine b) aminomethane
c) 2-aminopropane d) 2-aminoethanol
e) N-methylaminoethane -3- 10. Identify the Compound which gave the following spectra:
IR Spectrum ' H UV Spectrum IOO WAVELENGTH (MICRONS) 1'4 5 a 7 a 9 I u ,1: IAC I: so
I O 100 . 0 , H
no 50 O
_ 1— 70
3 ‘° 3 w a) so
I: m 50
3 ‘0 ‘° .0
: O 40
20 20 .0
‘ < so
0 , , 0
_4000 ”00 2000 1500 1200 1000 900 800 2°
' . 200nm. 400nm.
/ 10 ' In to u rel”) an n n to h
500 400 300 200 '00 0
I.- u m . u mu: ) u n m 1.0 - n MassSpectrum Intensity Additional Problems: m/e Solomons and F ryhle, 7‘h ed.
p. 988, NOS.: 20.23, 20.24, 20.25, 20.27, 20.28, 20.38. ...
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- Spring '08
- Organic chemistry