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Questions and Answers

Which reagent is used to convert a primary alcohol into an alkyl iodide via SN2?

HCl

TsCl

HI (correct)

PbBr3

Secondary alcohols undergo SN2 reactions for the conversion to alkyl halides.

False

What type of reaction occurs when using PBr3 to convert an alcohol to an alkyl bromide?

SN2

The conversion of alcohols to sulfonate esters involves the use of _____ as a reagent.

TsCl Signup and view all the answers

Match the reagent with its use in converting alcohols:

SOCl2 = Substitute Cl for OH in primary and secondary alcohols HCl ZnCl2 = Substitute Cl for OH in secondary alcohols PBr3 = Substitute Br for OH TsCl = Convert alcohol to sulfonate ester Signup and view all the answers

Which type of reaction occurs when using acetone as a solvent with NaCN?

SN2 Signup and view all the answers

Protic solvents promote SN2 reactions.

False Signup and view all the answers

What does Na2Cr2O7 do in organic reactions?

Oxidizes primary alcohols to carboxylic acids and secondary alcohols to ketones. Signup and view all the answers

H2SO4 undergoes elimination with alcohols via E1 for _ degree and E2 for _ degree.

tertiary; primary Signup and view all the answers

Match the reagents with their respective outcomes:

Na2Cr2O7 = Oxidizes 1° to COOH, 2° to ketones PCC = Mild oxidation: 1° to aldehyde, 2° to ketones H2SO4 = Elimination with alcohols NaCN = SN2 reaction in aprotic solvent Signup and view all the answers

What reagent is typically used in the Williamson ether synthesis?

Sodium and halogen Signup and view all the answers

Phenols are reactive in alcohols.

False Signup and view all the answers

What happens when ethers are treated with strong acid?

They can be cleaved. Signup and view all the answers

NaOCH3 opens epoxides in _ conditions for the most substituted carbon and in _ conditions for the least substituted carbon.

acidic, basic Signup and view all the answers

Match the reagents with their functions:

NaH = Deprotonates alcohols NaOCH3 = Opens epoxides Strong acid = Cleaves ethers Phenol = Unreactive in alcohols Signup and view all the answers

Study Notes

Conversion Methods of Alcohols to Alkyl Halides

HI Conversion: Primary alcohols react with hydroiodic acid (HI) via SN2 mechanism, resulting in the substitution of hydroxyl group (OH) with iodine (I).
HCl with ZnCl2: Secondary alcohols undergo conversion to alkyl halides by reacting with hydrochloric acid (HCl) in the presence of zinc chloride (ZnCl2), which facilitates an SN1 reaction, replacing OH with chlorine (Cl).
SOCl2 Reaction: Thionyl chloride (SOCl2) is effective for converting alcohols (including methanol, primary, and secondary) to alkyl chlorides through an SN2 mechanism, replacing OH with Cl.
PBr3 Utilization: Phosphorus tribromide (PBr3) converts alcohols to alkyl bromides using an SN2 pathway, where hydroxyl groups are substituents for bromine (Br).
TsCl Esterification: Tosyl chloride (TsCl) reacts with alcohols to form sulfonate esters (OTS), which enhance the leaving group potential of the hydroxyl group for further substitution reactions.

Reactions Overview

Sodium cyanide (NaCN) in acetone serves as a solvent conducive to SN2 reactions due to acetone being aprotic.
The choice of solvent affects nucleophilic substitution mechanisms:
- Aprotic solvents favor SN2 mechanism.
- Protic solvents promote SN1 mechanism.

Elimination Reactions with H2SO4

H2SO4 (sulfuric acid) can induce elimination reactions in alcohols:
- E1 (unimolecular elimination) is typical for tertiary (3°) and secondary (2°) alcohols.
- E2 (bimolecular elimination) is commonly observed with primary (1°) alcohols.

Oxidation Reactions

Sodium dichromate (Na2Cr2O7) acts as a strong oxidizing agent:
- Oxidizes primary alcohols (1°) to carboxylic acids (COOH).
- Oxidizes secondary alcohols (2°) to ketones.

PCC Oxidation

Pyridinium chlorochromate (PCC) is a mild oxidizing agent:
- Converts primary alcohols (1°) to aldehydes.
- Converts secondary alcohols (2°) to ketones.

Ethers

Williamson ether synthesis involves a nucleophilic substitution reaction between sodium (Na) and a halogen.
Sodium hydride (NaH) is used to deprotonate alcohols, enabling the formation of alkoxide ions.
Both sodium (Na) and lithium (Li) can facilitate the deprotonation process, with NaH being a key reagent.
Ethers are susceptible to cleavage by strong acids, which can break the ether bond.

Phenols and Epoxides

Phenols exhibit low reactivity in alcohols, making them stable under certain conditions.
Sodium methoxide (NaOCH3) can effectively open epoxide rings through nucleophilic attack.
Under acidic conditions, the most substituted carbon of the epoxide ring is typically targeted.
In basic conditions, the least substituted carbon is preferred for the nucleophilic attack and ring opening.

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Description

This quiz covers the methods for converting alcohols into alkyl halides, including procedures using various reagents such as HI, HCl with ZnCl2, SOCl2, and PBr3. Understand the differences between SN1 and SN2 mechanisms in these reactions. Test your knowledge on the steps and conditions for successful conversions.