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Ch.12 Alcohols, Thiols, Ethers, Aldehydes, and Ketones
Timberlake - Chemistry: An Introduction to General, Organic, and Biological Chemistry 14th Edition
Timberlake14th EditionChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9781292472249Not the one you use?Change textbook
All textbooksTimberlake 14th EditionCh.12 Alcohols, Thiols, Ethers, Aldehydes, and KetonesProblem 68
Chapter 12, Problem 68

Compound X is a secondary alcohol whose formula is C3H8O. When compound X is heated with strong acid, it dehydrates to form compound Y (C3H6). When compound X is oxidized, compound Z (C3H6O) forms, which cannot be oxidized further. Draw the condensed structural formulas and give the IUPAC names for compounds X, Y, and Z.

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1
Step 1: Identify the structure of compound X. Since compound X is a secondary alcohol with the formula C₃H₈O, it must have a hydroxyl group (-OH) attached to a secondary carbon. The possible structure is 2-propanol (CH₃-CHOH-CH₃).
Step 2: Determine the dehydration reaction. When 2-propanol is heated with a strong acid, it undergoes a dehydration reaction (loss of water) to form an alkene. The product, compound Y, is propene (CH₃-CH=CH₂).
Step 3: Analyze the oxidation of compound X. When 2-propanol is oxidized, the secondary alcohol is converted into a ketone. The product, compound Z, is acetone (CH₃-CO-CH₃), which has the formula C₃H₆O.
Step 4: Confirm that compound Z cannot be oxidized further. Ketones, such as acetone, do not undergo further oxidation under normal conditions because there is no hydrogen atom attached to the carbonyl carbon.
Step 5: Summarize the IUPAC names and condensed structural formulas. Compound X is 2-propanol (CH₃-CHOH-CH₃), compound Y is propene (CH₃-CH=CH₂), and compound Z is acetone (CH₃-CO-CH₃).

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Secondary Alcohols

Secondary alcohols are organic compounds where the hydroxyl (-OH) group is attached to a carbon atom that is itself connected to two other carbon atoms. This structure influences their reactivity, particularly in dehydration and oxidation reactions. In the case of compound X (C₃H₈O), it is a secondary alcohol, which means it can undergo dehydration to form an alkene and oxidation to form a ketone.
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Dehydration Reaction

A dehydration reaction involves the removal of a water molecule from a compound, often resulting in the formation of a double bond. In this scenario, when compound X is heated with strong acid, it loses a water molecule to form compound Y (C₃H₆), an alkene. This reaction is a common method for converting alcohols into alkenes and is facilitated by acidic conditions.
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Oxidation of Alcohols

Oxidation of alcohols refers to the chemical process where alcohols are converted into carbonyl compounds, such as aldehydes or ketones, by the addition of oxygen or the removal of hydrogen. In this case, when compound X is oxidized, it forms compound Z (C₃H₆O), which is a ketone. The fact that compound Z cannot be oxidized further indicates that it is a stable product, typically characteristic of ketones.
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Related Practice
Textbook Question

A compound with the formula C4H8O is synthesized from 2-methyl-1-propanol and oxidizes easily to give a carboxylic acid. Draw the condensed structural formula and give the IUPAC name for the compound.

Textbook Question

A compound with the formula C5H10O oxidizes to give 3-pentanone. Draw the condensed structural formula and give the IUPAC name for the compound.

Textbook Question

Compound A is a primary alcohol whose formula is C3H8O. When compound A is heated with strong acid, it dehydrates to form compound B (C3H6). When compound A is oxidized, compound C (C3H6O) forms. Draw the condensed structural formulas and give the IUPAC names for compounds A, B, and C.