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Reactions of Isopentyl Bromide with Various Reagents
Chapter 9, Problem 9.45(choose chapter or problem)
Give the products expected when isopentyl bromide (1-bromo-3-methylbutane) or the other substances indicated react with the following reagents.
(a) KI in aqueous acetone
(b) KOH in aqueous ethanol
(c) \(\mathrm{K}^{+}\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{O}^{-} \text {in }\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{OH} \)
(d) product of part (c) + HBr
(e) CsF in N,N-dimethylformamide (a polar aprotic solvent)
(f) product of part (c) + chloroform + potassium tert-butoxide
(g) product of part (c) + \(\mathrm{CH}_{2} \mathrm{I}_{2}\) in the presence of a Zn-Cu couple
(h) Li in hexane, then ethanol
(i) sodium methoxide in methanol
(j) Mg and anhydrous ether, then \(\mathrm{D}_{2} \mathrm{O}\)
Questions & Answers
QUESTION:
Give the products expected when isopentyl bromide (1-bromo-3-methylbutane) or the other substances indicated react with the following reagents.
(a) KI in aqueous acetone
(b) KOH in aqueous ethanol
(c) \(\mathrm{K}^{+}\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{O}^{-} \text {in }\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{OH} \)
(d) product of part (c) + HBr
(e) CsF in N,N-dimethylformamide (a polar aprotic solvent)
(f) product of part (c) + chloroform + potassium tert-butoxide
(g) product of part (c) + \(\mathrm{CH}_{2} \mathrm{I}_{2}\) in the presence of a Zn-Cu couple
(h) Li in hexane, then ethanol
(i) sodium methoxide in methanol
(j) Mg and anhydrous ether, then \(\mathrm{D}_{2} \mathrm{O}\)
ANSWER:Step 1 of 2
(a) Isopentyl bromide reacts with KI in aqueous acetone, forming 1-iodo-3-methylbutane:
\(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{Br}+\mathrm{KI} \rightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{I}+\mathrm{KBr}\)
(b) Isopentyl bromide reacts with KOH in aqueous ethanol, forming 3-methylbutane-1-ol:
\(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{Br}+\mathrm{KOH} \rightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{OH}+\mathrm{KBr}\)
(c) Isopentyl bromide reacts with potassium tert-butoxide in tert-butanol, forming 3-methylbut-1-ene (E2 elimination):
\(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{Br}+\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CO}-\rightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)=\mathrm{CH} 2+\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}+\mathrm{Br}-\)
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Reactions of Isopentyl Bromide with Various Reagents
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Explore the fascinating reactions of isopentyl bromide with a variety of reagents and uncover the expected products in each scenario.