Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure

Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook

Bruice 8th Edition

Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure

Problem 21b

Chapter 4, Problem 21b

Draw the structures and provide systematic names for parts a, b, and c by substituting a chlorine for a hydrogen of methylcyclohexane:
(b) a tertiary alkyl halide

Verified step by step guidance

Identify the structure of methylcyclohexane: Methylcyclohexane consists of a cyclohexane ring with a single methyl group (-CH₃) attached to one of the carbons in the ring.

Determine the location of a tertiary carbon in methylcyclohexane: A tertiary carbon is a carbon atom bonded to three other carbon atoms. In methylcyclohexane, the carbon in the cyclohexane ring that is directly bonded to the methyl group is a tertiary carbon.

Substitute a hydrogen atom on the tertiary carbon with a chlorine atom: Replace one of the hydrogens attached to the tertiary carbon with a chlorine atom to form the tertiary alkyl halide.

Draw the structure of the resulting compound: The structure will show the cyclohexane ring with the methyl group attached to one carbon, and a chlorine atom attached to the tertiary carbon (the same carbon bonded to the methyl group).

Provide the systematic name: The systematic name of the compound is 1-chloro-1-methylcyclohexane, where the chlorine atom is on the same carbon as the methyl group, which is the tertiary carbon.

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Key Concepts

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

Methylcyclohexane Structure

Methylcyclohexane is a cycloalkane with a methyl group (-CH3) attached to a cyclohexane ring. Understanding its structure is crucial for identifying where substitutions can occur. The cyclohexane ring consists of six carbon atoms arranged in a hexagonal shape, with hydrogen atoms filling the remaining valences. This foundational knowledge helps in visualizing how chlorine can replace hydrogen atoms in the molecule.

Tertiary Alkyl Halides

A tertiary alkyl halide is a compound where a halogen atom (like chlorine) is bonded to a carbon atom that is itself attached to three other carbon atoms. This structure is significant because it influences the reactivity and stability of the compound. Tertiary alkyl halides typically undergo nucleophilic substitution reactions more readily than primary or secondary alkyl halides due to steric hindrance and the stability of the resulting carbocation.

Nomenclature of Organic Compounds

Systematic naming of organic compounds follows the IUPAC (International Union of Pure and Applied Chemistry) rules, which provide a standardized method for naming chemical structures. For alkyl halides, the name includes the longest carbon chain, the position of the halogen substituent, and the type of halogen. Understanding these rules is essential for accurately naming the substituted products derived from methylcyclohexane.

Draw the structures and provide systematic names for parts a, b, and c by substituting a chlorine for a hydrogen of methylcyclohexane: (b) a tertiary alkyl halide