Solution Found!
Predict the products and mechanisms of the following
Chapter 8, Problem 40P(choose chapter or problem)
Predict the products and mechanisms of the following reactions. When more than one product or mechanism is possible, explain which are most likely.
(a) 1-bromohexane sodium ethoxide in ethanol
(b) 2 -chlorohexane + \(\mathrm{NaOCH}_{3}\) in methanol
(c) 2 -chloro-2-methylbutane + \(\mathrm{NaOCH}_{2} \mathrm{CH}_{3}\) in ethanol
(d) 2 -chloro-2-methylbutane heated in ethanol
(e) isobutyl iodide + \(\mathrm{KOH}\) in ethanol/water
(f) isobutyl chloride + \(\mathrm{AgNO}_{3}\) in ethanol in ethanol/water
(g) 1-bromo-1-methylcyclopentane + \(\mathrm{NaOEt}\) in ethanol
(h) 1-bromo-1-methylcyclopentane heated in methanol
Equation Transcription:
Text Transcription:
NaOCH_3
NaOCH_2CH_3
KOH
AgNO_3
NaOEt
Questions & Answers
QUESTION:
Predict the products and mechanisms of the following reactions. When more than one product or mechanism is possible, explain which are most likely.
(a) 1-bromohexane sodium ethoxide in ethanol
(b) 2 -chlorohexane + \(\mathrm{NaOCH}_{3}\) in methanol
(c) 2 -chloro-2-methylbutane + \(\mathrm{NaOCH}_{2} \mathrm{CH}_{3}\) in ethanol
(d) 2 -chloro-2-methylbutane heated in ethanol
(e) isobutyl iodide + \(\mathrm{KOH}\) in ethanol/water
(f) isobutyl chloride + \(\mathrm{AgNO}_{3}\) in ethanol in ethanol/water
(g) 1-bromo-1-methylcyclopentane + \(\mathrm{NaOEt}\) in ethanol
(h) 1-bromo-1-methylcyclopentane heated in methanol
Equation Transcription:
Text Transcription:
NaOCH_3
NaOCH_2CH_3
KOH
AgNO_3
NaOEt
ANSWER:
Solution 40P
(a)
1-bromohexane is a primary alkyl halide and in presence of a strong base (sodium ethoxide) it mainly undergoes SN2 and possibly E2.
1- bromohexane + Nain
2
ethanol (and possibly E2)
Since 1-bromohexane is primary halide, so it undergoes mainly 2 and as Na
is strong base, so E2 reaction may also be observed.
(b)
2-chlorohexane is secondary alkyl halide and in presence of a strong base (sodium ethoxide) it undergoes both SN2 and E2 reaction to give a mixture of products.
2-chlorohexane and E2
Na is strong nucleophile (or base), so it will force second order kinetics, either
2 or E2 and since the halide is 2º, so both can occur.
Mechanism:
(c)
2-chloro-2-methylbutane is tertiary alkyl halide and in presence of strong base (sodium ethoxide) it undergoes E2 reaction to form more substituted alkene as a major product.