ORGANIC CHEMISTRY-STD.WILEY PLUS CARD
3rd Edition
ISBN: 9781119340515
Author: Klein
Publisher: WILEY
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Chapter 10, Problem 57IP
Interpretation Introduction
Interpretation:
From the given intermediates, the intermediate formed when 1-butene undergoes radical bromination has to be identified.
Concept introduction:
Stability of Radicals: Radicals are highly unstable due to its unpaired valence electron of an atom.
The increasing order of radical stability is given below
Benzylic > allylic > tertiary > secondary > primary > methyl
Bond strength is depends on the formation of the radical, if the radical is involving in resonance which weakest bond strength.
Radical Bromination:
2-methyl propane undergoes radical bromination which yields the 2-bromo-2-methylpropane.because bromination will occur where the tertiary radical is present. (Bromination reactions are more selective reaction).
Bromination will occur on tertiary radical than the secondary than primary radical, tertiary radical is more stable radical than the other radicals.
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2. Consider the data below to answer the following questions.
Cyanohydrins are important intermediates in the synthesis of α-hydroxycarboxylic acids from ketones and
aldehydes. The nitrile functional group can be hydrolyzed by aqueous acid to yield a carboxylic acid.
Nitriles can also be hydrolyzed to carboxylic acids using aqueous base. Unfortunately, when a cyanohydrin
is treated with aqueous base the original carbonyl compound is isolated.
OH
CH-COOH
0
HO CN
C
H30*
C.
H
H
HC N
NaOH
H₂O
C=O
0
cyanohydrin
H
+ NaCN + H₂O
Assign all integrated peaks
- Consider the data in the Table below to answer the following questions:
Acidities of Substituted Benzoic and Acetic Acids
pk,s at 25C
Y-CH COOH
Y
Y - CH₂COOH
meta
para
H
4.75
4.19
4.19
2.47
3.64
3.55
3.57
4.09
4.46
CN
OCH 3
A. Draw the structure of the strongest acid in the table above.
B. Explain why cyanoacetic acid and methoxyacetic acid are more acidic than their correspondingly
substituted benzoic acid counterparts.
Chapter 10 Solutions
ORGANIC CHEMISTRY-STD.WILEY PLUS CARD
Ch. 10.1 - Prob. 1CCCh. 10.1 - Prob. 1LTSCh. 10.1 - Prob. 2PTSCh. 10.1 - Prob. 3PTSCh. 10.1 - Prob. 4ATSCh. 10.1 - Prob. 2LTSCh. 10.1 - Prob. 5PTSCh. 10.1 - Prob. 6PTSCh. 10.1 - Prob. 7ATSCh. 10.2 - Prob. 3LTS
Ch. 10.2 - Prob. 8PTSCh. 10.2 - Prob. 9ATSCh. 10.3 - Prob. 4LTSCh. 10.3 - Prob. 10PTSCh. 10.3 - Prob. 11ATSCh. 10.5 - Prob. 5LTSCh. 10.5 - Prob. 12PTSCh. 10.5 - Prob. 13ATSCh. 10.6 - Prob. 6LTSCh. 10.6 - Prob. 14PTSCh. 10.6 - Prob. 15ATSCh. 10.7 - Prob. 7LTSCh. 10.7 - Prob. 16PTSCh. 10.7 - Prob. 17PTSCh. 10.7 - Prob. 18ATSCh. 10.8 - Prob. 19CCCh. 10.9 - Prob. 20CCCh. 10.10 - Prob. 8LTSCh. 10.10 - Prob. 21PTSCh. 10.10 - Prob. 22ATSCh. 10 - Prob. 23PPCh. 10 - Prob. 24PPCh. 10 - Prob. 25PPCh. 10 - Prob. 26PPCh. 10 - Prob. 27PPCh. 10 - Prob. 28PPCh. 10 - Prob. 29PPCh. 10 - Prob. 30PPCh. 10 - Prob. 31PPCh. 10 - Prob. 32PPCh. 10 - Prob. 33PPCh. 10 - Prob. 34PPCh. 10 - Prob. 35PPCh. 10 - Prob. 36PPCh. 10 - Prob. 37PPCh. 10 - Prob. 38PPCh. 10 - Prob. 39PPCh. 10 - Prob. 40PPCh. 10 - Prob. 41IPCh. 10 - Prob. 42IPCh. 10 - Prob. 43IPCh. 10 - Prob. 44IPCh. 10 - Prob. 45IPCh. 10 - Prob. 46IPCh. 10 - Prob. 47IPCh. 10 - Prob. 48IPCh. 10 - Prob. 49IPCh. 10 - Prob. 50IPCh. 10 - Prob. 51IPCh. 10 - Prob. 52IPCh. 10 - Prob. 53IPCh. 10 - Prob. 54IPCh. 10 - Prob. 55IPCh. 10 - Prob. 56IPCh. 10 - Prob. 57IPCh. 10 - Prob. 58CPCh. 10 - Prob. 59CPCh. 10 - As seen in this chapter, hydrocarbons typically do...Ch. 10 - Prob. 61CP
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