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Chapter 8: Q19Q (page 395)

Propose a mechanism for the addition of bromine water to cyclopentene, being carefulto show why the trans product results and how both enantiomers are formed.

Short Answer

Expert verified

first step is addition of a bromine molecule to cyclopentene ring to form bromonium ion.

Step by step solution

01

Step 1:

first step is addition of a bromine molecule to cyclopentene ring to form bromonium ion.

02

 

Now water molecule is added in the second step. Here two possibilities occur due to the presence of bromonium ion. first if water attack from the back side (dash bond) then bromine come upward (wedge bond) while if water molecule attack from the front side(wedge bond) then bromine go backward(dash bond). The two products formed are enantiomers as the only difference in orientation of the bromine atom and hydroxyl group

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Most popular questions from this chapter

Limonene is one of the compounds that give lemons their tangy odour.Show the structures of the products expected when limonene reacts with an excess of each of these reagents.

(a) Borane in tetrahydrofuran, followed by basic hydrogen peroxide

(b) m-chloroperoxybenzoic acid

(c) ozone, then dimethyl sulfide

(d) a mixture of osmic acid and hydrogen peroxide

(e) hot, concentrated potassium permanganate

(f) peroxyacetic acid in acidic water

(g) hydrogen and a platinum catalyst

(h) hydrogen bromide gas

(i) hydrogen bromide gas in a solution containing dimethyl peroxide

(j) bromine water

(k) chlorine gas

(l) mercuric acetate in methanol, followed by sodium borohydride

(m) CHBr3 and 50% aq. NaOH

Sketch the expected proton NMR spectra of 3,3- dimethylbutanal.

Predictthe major products of the following reactions.

a. E- 3-methyloct-3-ene+ ozone, then Me3S

b. Z- 3-methyloct-3-ene+ ozone, then Me3S

e. 1-ethylcycloheptene + ozone, then Me2S

f. 1-ethylcycloheptene + warm, then KMnO4

g. 1-ethylcycloheptene + cold,, dil.KMnO4

The chiral BINAP ligand shown in figure 8-8 contains no asymmetric carbon atoms. Explain how this ligand is chiral.

Question: Show how you would accomplish the following conversions.

(a)Cis-hex-3-ene to meso-hexane-3,4-diol

(b)Cis-hex-3-ene to (d,l)-hexane-3,4-diol

(c)Trans-hex-3-ene to meso-hexane-3,4-diol

(d)Trans-hex-3-ene to (d,l)-hexane-3,4-diol
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