Fluorination of alkane free radical subsitutisn example of to is aud it leads formation ol mixture of various mono hala. products. CH - CH- CH, -CH3 2°c CHy- - CH- CH, -CH,-F | CH2- 3°c I'C CH - CH- CH -CH2 F -c - CH,-CHy + F- CH,-CH-CH,-CH3 fow Oalulogeneted

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Chapter1: Chemical Foundations
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Using the table determine which products are major in halogenation reaction Then draw arrows pushing mechanisms to explain formation of major product.
2-Bromo
(tert-Butyl bromide)
90%
10%
Less (primary)
0.06%
Expected (statistical) ratio
C-H bond reactivity
Experimental ratio
More (tertiary)
99.94%
In Summary Increased reactivity goes hand in hand with reduced selectivity in radioa
stitution reactions. Fluorine and chlorine, the more reactive halogens, discriminate ha
the various types of C-H bonds much less than does the less reactive bromine (Table 3
Relative Reactivities of the Four Types of Alkane C-H Bonds
in Halogenations
Table 3-6
F•
C-H bond
Cl•
(25°C, gas)
(25°C, gas)
Br.
(150°C, g
CH3-H
RCH,-H"
R,CH-H
R;C-H
0.5
0.004
1
0.002
1.2
1
1
1.4
4
80
primary C-H bond.
1700
Transcribed Image Text:2-Bromo (tert-Butyl bromide) 90% 10% Less (primary) 0.06% Expected (statistical) ratio C-H bond reactivity Experimental ratio More (tertiary) 99.94% In Summary Increased reactivity goes hand in hand with reduced selectivity in radioa stitution reactions. Fluorine and chlorine, the more reactive halogens, discriminate ha the various types of C-H bonds much less than does the less reactive bromine (Table 3 Relative Reactivities of the Four Types of Alkane C-H Bonds in Halogenations Table 3-6 F• C-H bond Cl• (25°C, gas) (25°C, gas) Br. (150°C, g CH3-H RCH,-H" R,CH-H R;C-H 0.5 0.004 1 0.002 1.2 1 1 1.4 4 80 primary C-H bond. 1700
example of
to
free radical substtutisn and it leads
is
Fluorination of alkane
an
moro halo.
poducts.
formetion ol mixture of various
CH2
Fa
CH2-CH- CH2-CH3
2°c'
CHy-CH- CH,-CH,F
|
3°c
CH - CH- CH -CH2
F
- си, —снg
-
CHz
F- CH,-CH- CH,-CHz
four monokalogeneted
products
Transcribed Image Text:example of to free radical substtutisn and it leads is Fluorination of alkane an moro halo. poducts. formetion ol mixture of various CH2 Fa CH2-CH- CH2-CH3 2°c' CHy-CH- CH,-CH,F | 3°c CH - CH- CH -CH2 F - си, —снg - CHz F- CH,-CH- CH,-CHz four monokalogeneted products
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