a) Bromobenzene, 2-bromopropane, bromoethane
Interpretation:
The compounds bromoethane, 2-bromopropane and bromobenzene are to be ranked in the order of their reactivity in Williamson synthesis.
Concept introduction:
In Williamson synthesis, the primary
To rank:
The compounds bromoethane, 2-bromopropane and bromobenzene in the order of their reactivity in Williamson synthesis.
b) Chloroethane, bromoethane, 1-Iodopropene
Interpretation:
The compounds chloroethane, bromoethane and 1-iodopropene are to be ranked in the order of their reactivity in Williamson synthesis.
Concept introduction:
In Williamson synthesis, te alkoxuide reacts with primary alkyl halides through a SN2 mechanism. The requirements are thus a backside attack, a stronger nucleophile and a better leaving group. Among the halides, iodine is better leaving than bromine which in turn is a better leaving than chlorine. Vinyl halides are less reactive than alkyl halides.
To rank:
The compounds chloroethane, bromoethane and 1-iodopropene in the order of their reactivity in Williamson synthesis.
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Chapter 18 Solutions
Organic Chemistry
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- A certain hydrocarbon, C5H6, yields the two products shown below upon ozonolysis with 1. O3/CH2Cl2 2. Zn/H3O . Deduce the structure of the hydrocarbon.arrow_forwardModify the structure of 3-methyl-1-pentene to show the product formed when it is reacted with: Hydrogen chloride (HCl). Show relevant stereochemistry when applicable. A dilute aqueous solution of sulfuric acid (H2SO4). Show relevant stereochemistry when applicable. Diborane (B2H6) in diglyme, followed by basic hydrogen peroxide (H2O2, OH−). Show relevant stereochemistry when applicable. Bromine (Br2) in water. Show relevant stereochemistry when applicable. Peroxyacetic acid (CH3CO3H). Do not include stereochemistry.arrow_forwardThe above reaction involves heterolytic bond breakage of HBr a) Encircle the nucleophile (s) and electrophile (s) and explain why. b) Give the mechanism of the reaction by: ) Drawing the appropriate arrows to track the flow of electrons in Showing the species formed after bond breakage and bond formation with appropriate charges. c) Predict the final products.arrow_forward