Solution Found!

Reactions of Isopentyl Bromide with Various Reagents

Chapter 9, Problem 9.45

(choose chapter or problem)

Get Unlimited Answers! Check out our subscriptions
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 \(\mathrm{D}_{2} \mathrm{O}\)

Watch The Answer!

Reactions of Isopentyl Bromide with Various Reagents
Stars

Want To Learn More? To watch the entire video and ALL of the videos in the series:

Add to cart

Explore the fascinating reactions of isopentyl bromide with a variety of reagents and uncover the expected products in each scenario.

Not The Solution You Need? Search for Your Answer Here:

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):

\(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{Br}+\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CO}-\rightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)=\mathrm{CH} 2+\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}+\mathrm{Br}-\)

Add to cart


Study Tools You Might Need

×

Login

Login or Sign up for access to all of our study tools and educational content!

Forgot password?
Register Now

×

Register

Sign up for access to all content on our site!

Or login if you already have an account

×

Reset password

If you have an active account we’ll send you an e-mail for password recovery

Or login if you have your password back