Draw the organic product(s) formed when CH3 CH2 CH2 OH is treated with 9.43 each reagent. a. H2

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Draw the organic product(s) formed when CH3 CH2 CH2 OH is...

Draw the organic product(s) formed when $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}$ is treated with 9.43 each reagent. a. $\mathrm{H}_{2} \mathrm{SO}_{4}$ b. NaH c. HCl + $\mathrm{ZnCl}_{2}$ d. HBr e. SOCl $_{2}$, pyridine f. $\mathrm{PBr}_{3}$ g.TsCl, pyridine h. [1] NaH; [2] CH $_{3}$ CH $_{2}$ Br i. [1] TsCl, pyridine; [2] NaSH j. $\mathrm{POCl}_{3}$, pyridine

Draw the organic product(s) formed when $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}$ is treated with
9.43 each reagent.
a. $\mathrm{H}_{2} \mathrm{SO}_{4}$
b. NaH
c. HCl + $\mathrm{ZnCl}_{2}$
d. HBr
e. SOCl $_{2}$, pyridine
f. $\mathrm{PBr}_{3}$
g.TsCl, pyridine
h. [1] NaH; [2] CH $_{3}$ CH $_{2}$ Br
i. [1] TsCl, pyridine; [2] NaSH
j. $\mathrm{POCl}_{3}$, pyridine

Key Concepts

Tosylate Formation and Subsequent Substitution

Converting an alcohol into a tosylate using reagents like TsCl in the presence of pyridine transforms the poor leaving group (OH) into a good leaving group (OTs). The activated tosylate can then undergo nucleophilic substitution reactions, allowing for the synthesis of ethers, thiols, or other substituted products under mild conditions.

Alkoxide Formation Using Strong Bases

Treating alcohols with strong bases such as NaH results in the deprotonation of the hydroxyl group, forming an alkoxide. Alkoxides are potent nucleophiles that participate in SN2 reactions, enabling transformations like ether formation in Williamson Ether Synthesis or further substitution reactions in organic synthesis.

Williamson Ether Synthesis

Williamson Ether Synthesis is a classical method for preparing ethers by reacting an alkoxide ion (generated by deprotonating an alcohol with a strong base such as NaH) with a primary alkyl halide under SN2 conditions. This process demonstrates the utility of converting alcohols to nucleophilic species that can form carbon–oxygen bonds selectively.

Dehydration of Alcohols

Dehydration involves converting an alcohol into an alkene by removing a water molecule. In acid?catalyzed dehydration, the hydroxyl group is first protonated to form a better leaving group, which then departs to form a carbocation intermediate (or proceeds via an E2 mechanism for less substituted alcohols), followed by deprotonation to yield the alkene.

Alcohol Halogenation Reactions

Alcohol halogenation replaces the hydroxyl group with a halide, forming an alkyl halide. Reagents like HCl, HBr, SOCl2, and PBr3 are used in these reactions, with the mechanism (SN1 or SN2) largely determined by the alcohol’s structure and reaction conditions. Such transformations are fundamental in converting functional groups for further synthetic applications.

Lucas Test and Substitution Mechanisms

The Lucas test, which employs HCl in the presence of ZnCl2, differentiates alcohol reactivity based on their substitution. While tertiary alcohols typically react via an SN1 mechanism showing rapid cloudiness, primary alcohols proceed via an SN2 mechanism. This concept highlights the influence of molecular structure on the pathway and rate of nucleophilic substitution.

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