Kimia-1-UV
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Transcript of Kimia-1-UV
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ULTRAVIOLET SPECTROCOPY (UV)ULTRAVIOLET SPECTROCOPY (UV)[[ : 100-190 (Vacuum UV), 190-400 (Near UV)]
ELECTRON TRANSITION BETWEEN ELETRONIC ENERGY LEVEL (n)
* (max 200 nm) * (max: 200-700
nm)n * (max: 150-250
nm)n * (max: 200-700
nm)
CHROMOPHORIC GROUP OF ORGANIC COMPOUND
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CHROMOPHORIC GROUP
ABSORB ULTRAVIOLET ENERGY
CONJUGATED AND UNCONJUGATED DIENE CONJUGATED AND UNCONJUGATED TRIENE COMBINATION DIENE AND TRIENE KETONE CONJUGATED AND UNCONJUGATED OF UNSATURATED KETONE etc
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THE MAIN TERMINOLOGIES OF THE UV SPECTROSCOPY
CHROMOPHORIC GROUPAUXOCHROME GROUP
RED SHIFT (BATOCHROMIC SHIFT)BLUE SHIFT (HYPSOCHROMIC SHIFT)
HYPERCHROMIC EFFECTHYPOCHROMIC EFFECT
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maks = 256 nmmaks = 200 maks = 270 nm
maks = 1450
OHAuxochrome group
AUXOCHROME GROUP
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BATOCHROMIC-HYPSOCHROMIC SHIFT AND HYPERCHROMIC-HYPOCHROMIC EFFECT
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METHOD FOR PREDICTING THE MAXIMUM WAVELENGTH ( maks) OF UV ABSORBTION OF
ORGANIC COMPOUND
WOODWARD RULES
CONJUGATED DIENE ENONE
SUBTITUTED BENZENE
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WOODWARD RULE FORCONJUGATED DIENE
BASE VALUE OF max : 1. ACYCLIC DIENE AND HETEROANNULAR ………………215 nm 2. HOMOANNULAR DIENE..……………………………………253 nm
INCREMENTS FOR: 1. – R (ALKYL) …………+ 5 nm 2. – OR (ALCOXY)……………+6 nm 3. – SR (TIOPHENE)……………………...+30 nm 4. – Cl, Br……………………………………...+5 nm 5. – OCOR ………………………………………....+0 nm 6. EXTENDING CONJUGATION –CH=CH-……………..+30 nm 7. EXOCYCLIC DOUBLE BOND…….………………………+5 nm
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EXERCISES
CH2
CH2(a)
H3C CH3
(b) (c)
(d)(e)
AcO
(f)
AcO
(g)
HO
(h)
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EXAMPLE OF UV SPECTRUM
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WOODWARD RULE FOR ENONE
BASE VALUE OF max: AND 1. ACYCLIC ,-UNSATURATED KETONES AND SIX MEMBERED CYCLIC ,-UNSATURATED KETONES ….....................................215 nm 2. FIVE MEMBERED CYCLIC ,-UNSATURATED KETONES ……202 nm 3. ,-UNSATURATED ALDEHYDES………………… ……………..207 nm 4. ,-UNSATURATED CARBOXYLIC ACIDS AND ESTERS ……..195 nm
INCREMENTS FOR: 1. – R (ALKYL) ………………………+ 10 (), 12 (), 18 ( ), 18 () nm 2. – OR ……………………………….+ 35 ( ), 30 ( ), 17 ( ), 30 () nm 3. – SR…………………………………+ 85 () nm 4. – OH…………………………….....+35 ( ), 30 ( ), - (), 50 () nm 5. – Cl………………………….....…...+ 15 (), 12 () nm 6. – Br…………………………….…...+25 (), 30 () nm 7. – OCOR , -OCOAr…………..……+ 6 (, , , ) nm 8. – NR2…………………………...….+95 () nm 9. EXTENDING CONJUGATION –CH=CH-………………+30 nm 10. EXOCYCLIC DOUBLE BOND…….………………………+5 nm 11. HOMODIENE COMPONENT ………………………….+ 39 nm
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EXERCISES
H3C
H3C
O
CH3
(a)
H3C
H3C
O
CH3OH
(b)
O
OCH3(c)
O
OH
OCH3
(d)
O
OH
(e)
H3CO
O
OC2H5
(f)
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FIESER-KUHN RULE FOR POLIENE
max = 114 + 5 M + n (48 – 1,7 n) – 16,5 Rendo – 10 Rexo nm Max = (1,74 X 104) n
n = Sum of conjugated double bondM = Sum of alkyl group or like alkyl group on conjugated systemR endo = Sum of ring with endocyclic double bond on conjugated systemR exo = Sum of ring with exocyclic double bond on conjugated system
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EXERCISES
O
HO
O
OH
(a)
O
CH3
HO
(b)
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EXERCISES
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EXERCISES
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THE SUBTITUTED BENZENE
BASE VALUE maks OF PARENT CHROMOPHORES: 1. Z = R OR RING RESIDUE …………………….………………….....246 nm 2. Z = H ……………………………………………………………………..250 nm 3. Z = OH OR OR …………………………….………………………..230 nm INCREMENTS FOR: ortho meta para 1. – ALKYL /RING RESIDUE………… 3 3 10 2. – OH,OR ………………………………. 7 7 25 3. – O………………………………………11 20 78 4. – Cl………………………….....……….. - - 10 5. – Br…………………………….……….. 2 2 15 6. – NH2………………………...……..…..13 13 58 8. – NHAc….…………………………...…20 20 45 9. –NHMe…………………………….…….- - 73 10. –NMe2…………….……………………20 20 85
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EXERCISES
(a)
O
OC2H5
H2N
OCH3(b)
O
OH
H3CO
O(c)
O
(d)
Cl CH3 O
OC2H5
(e)O
H3CO
OCH3