Practice Questions

Apply IUPAC nomenclature rules to name the compound with the structure $\text{CH}_3\text{CH(OH)CH}_2\text{CH}_2\text{Cl}$.

Identify the class of alcohol (primary, secondary, or tertiary) for the compound with the IUPAC name 2-methylpropan-2-ol.

List two general methods for the preparation of alcohols from carbonyl compounds.

Recall the common name for the compound 2,4,6-trinitrophenol.

Solve for the major product of the Reimer-Tiemann reaction when phenol is treated with chloroform ($\text{CHCl}_3$) in the presence of aqueous NaOH.

Define a symmetrical ether and provide one example.

Name the major product formed when phenol is heated with zinc dust.

Apply your knowledge of electrophilic substitution to predict the major product of the bromination of anisole in ethanoic acid.

Critique the proposed synthesis of t-butyl ethyl ether from the reaction of sodium ethoxide ($C_2H_5ONa$) with t-butyl chloride ($(CH_3)_3CCl$). Propose a more suitable synthetic route.

Justify why the phenoxide ion, rather than phenol itself, is used as the reactant in the Kolbe's reaction for the synthesis of salicylic acid.

Demonstrate how you would convert propene to propan-1-ol using the hydroboration-oxidation reaction. Write the complete reaction sequence.

Describe the industrial preparation of phenol from cumene. Write all the chemical equations involved in the process.

Summarize the reaction known as the Reimer-Tiemann reaction by stating the reactants, conditions, and the major product formed. Write the overall chemical equation.

Explain why phenols are more acidic than alcohols.

Compare the acidity of phenol, p-nitrophenol, and p-cresol. Arrange them in increasing order of acidity and justify your answer based on substituent effects.

Analyze the reaction of ethanol with concentrated $\text{H}_2\text{SO}_4$ at two different temperatures: $413 \text{ K}$ and $443 \text{ K}$. Identify the major product in each case and explain the difference.

Compare the boiling points of propan-1-ol, butan-1-ol, and butan-2-ol. Analyze the structural factors responsible for the differences.

Solve for the synthesis of 2-methylpropan-2-ol starting from a suitable ketone and a Grignard reagent. Show the reaction steps.

Examine the products formed when anisole (methoxybenzene) is heated with excess concentrated HI.

Demonstrate the industrial preparation of phenol from cumene. Analyze the economic importance of acetone being formed as a by-product in this process.

Apply the concept of oxidation to predict the major products when (i) propan-1-ol is treated with pyridinium chlorochromate (PCC) and (ii) propan-2-ol is treated with chromic anhydride ($\text{CrO}_3$). Write the reactions.

Compare the reactions of primary, secondary, and tertiary alcohols with Lucas reagent (conc. $\text{HCl}$ and anhydrous $\text{ZnCl}_2$). Analyze how this test can be used to distinguish between the three classes of alcohols.

Evaluate the reaction outcomes when ethanol is treated with concentrated sulphuric acid ($H_2SO_4$) at two different temperatures: $413$ K and $443$ K. Justify why different major products are formed.

Create a flowchart to design a series of chemical tests to distinguish between propan-1-ol, propan-2-ol, and 2-methylpropan-2-ol. Justify the expected observations for each test.

Explain why the boiling point of ethanol ($C_2H_5OH$) is significantly higher than that of methoxymethane ($CH_3OCH_3$), although they have comparable molecular masses.

List the products formed when anisole undergoes Friedel-Crafts alkylation with methyl chloride ($CH_3Cl$) in the presence of anhydrous aluminum chloride ($AlCl_3$). Identify the major product.

Name the reagent commonly used to distinguish between primary, secondary, and tertiary alcohols in the laboratory.

Write the IUPAC names for the following compounds: (i) Glycerol, (ii) Catechol, and (iii) Anisole.

Examine the solubility of butan-1-ol and pentan-1-ol in water. Compare their solubilities with that of diethyl ether, which has a comparable molecular mass to butan-1-ol. Analyze the role of hydrogen bonding and the hydrophobic alkyl chain.

Explain the mechanism of acid-catalysed dehydration of ethanol to yield ethene. Show all the steps involved.

Demonstrate the complete mechanism for the acid-catalyzed dehydration of propan-2-ol to form propene. Analyze why this reaction is faster for tertiary alcohols.

Name the reactants required for the preparation of t-butyl ethyl ether using Williamson synthesis and explain why the alternative combination of reactants is not suitable.

Describe the classification of monohydric alcohols based on the hybridization of the carbon atom to which the hydroxyl group is attached. Provide one example for each classification.

Contrast the Williamson synthesis of t-butyl ethyl ether using two different sets of reactants: (i) sodium ethoxide and t-butyl chloride, and (ii) sodium t-butoxide and ethyl chloride. Analyze why one pathway is successful while the other fails.

Propose a detailed mechanism for the cleavage of t-butyl methyl ether with excess concentrated HI. Justify why the reaction follows an $S_N1$ pathway.

Design a multi-step synthesis to prepare 1-phenylethanol starting from benzene. You may use any necessary inorganic reagents and organic reagents with up to two carbon atoms. Justify the choice of reagents for each step.