12: Organic Chemistry - Alkanes and Halogenated Hydrocarbons
- Page ID
- 15931
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\(\newcommand{\avec}{\mathbf a}\) \(\newcommand{\bvec}{\mathbf b}\) \(\newcommand{\cvec}{\mathbf c}\) \(\newcommand{\dvec}{\mathbf d}\) \(\newcommand{\dtil}{\widetilde{\mathbf d}}\) \(\newcommand{\evec}{\mathbf e}\) \(\newcommand{\fvec}{\mathbf f}\) \(\newcommand{\nvec}{\mathbf n}\) \(\newcommand{\pvec}{\mathbf p}\) \(\newcommand{\qvec}{\mathbf q}\) \(\newcommand{\svec}{\mathbf s}\) \(\newcommand{\tvec}{\mathbf t}\) \(\newcommand{\uvec}{\mathbf u}\) \(\newcommand{\vvec}{\mathbf v}\) \(\newcommand{\wvec}{\mathbf w}\) \(\newcommand{\xvec}{\mathbf x}\) \(\newcommand{\yvec}{\mathbf y}\) \(\newcommand{\zvec}{\mathbf z}\) \(\newcommand{\rvec}{\mathbf r}\) \(\newcommand{\mvec}{\mathbf m}\) \(\newcommand{\zerovec}{\mathbf 0}\) \(\newcommand{\onevec}{\mathbf 1}\) \(\newcommand{\real}{\mathbb R}\) \(\newcommand{\twovec}[2]{\left[\begin{array}{r}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\ctwovec}[2]{\left[\begin{array}{c}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\threevec}[3]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\cthreevec}[3]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\fourvec}[4]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\cfourvec}[4]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\fivevec}[5]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\cfivevec}[5]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\mattwo}[4]{\left[\begin{array}{rr}#1 \amp #2 \\ #3 \amp #4 \\ \end{array}\right]}\) \(\newcommand{\laspan}[1]{\text{Span}\{#1\}}\) \(\newcommand{\bcal}{\cal B}\) \(\newcommand{\ccal}{\cal C}\) \(\newcommand{\scal}{\cal S}\) \(\newcommand{\wcal}{\cal W}\) \(\newcommand{\ecal}{\cal E}\) \(\newcommand{\coords}[2]{\left\{#1\right\}_{#2}}\) \(\newcommand{\gray}[1]{\color{gray}{#1}}\) \(\newcommand{\lgray}[1]{\color{lightgray}{#1}}\) \(\newcommand{\rank}{\operatorname{rank}}\) \(\newcommand{\row}{\text{Row}}\) \(\newcommand{\col}{\text{Col}}\) \(\renewcommand{\row}{\text{Row}}\) \(\newcommand{\nul}{\text{Nul}}\) \(\newcommand{\var}{\text{Var}}\) \(\newcommand{\corr}{\text{corr}}\) \(\newcommand{\len}[1]{\left|#1\right|}\) \(\newcommand{\bbar}{\overline{\bvec}}\) \(\newcommand{\bhat}{\widehat{\bvec}}\) \(\newcommand{\bperp}{\bvec^\perp}\) \(\newcommand{\xhat}{\widehat{\xvec}}\) \(\newcommand{\vhat}{\widehat{\vvec}}\) \(\newcommand{\uhat}{\widehat{\uvec}}\) \(\newcommand{\what}{\widehat{\wvec}}\) \(\newcommand{\Sighat}{\widehat{\Sigma}}\) \(\newcommand{\lt}{<}\) \(\newcommand{\gt}{>}\) \(\newcommand{\amp}{&}\) \(\definecolor{fillinmathshade}{gray}{0.9}\)We begin our study of organic chemistry with the alkanes, compounds containing only two elements, carbon and hydrogen, and having only single bonds. There are several other kinds of hydrocarbons, distinguished by the types of bonding between carbon atoms and by the properties that result from that bonding. We will first examine hydrocarbons with double bonds, with triple bonds, and with a special kind of bonding called aromaticity. Then we will study some compounds considered to be derived from hydrocarbons by replacing one or more hydrogen atoms with an oxygen-containing group. Finally, we focuse on organic acids and bases, after which we will be ready to look at the chemistry of life itself—biochemistry—in the remaining five chapters.
- 12.0: Prelude to Organic Chemistry - Alkanes and Halogenated Hydrocarbons
- This page discusses hydrocarbons, highlighting their varying physiological effects based on molecular size. Low molar mass alkanes can be used as anesthetics but may cause serious health risks when inhaled. Liquid ingestion can result in chemical pneumonia. Medium-chain alkanes can harm skin oils, while heavier alkanes function as skin emollients. Additionally, hydrocarbon products like mineral oil and petroleum jelly offer protective benefits for sensitive skin.
- 12.1: Organic Chemistry
- This page distinguishes between organic and inorganic compounds, detailing their historical development. Organic compounds are carbon-based and initially linked to living organisms, while inorganic compounds include other elements. It mentions Friedrich Wöhler's synthesis of urea, which challenged the idea of a unique "vital force.
- 12.2: Structures and Names of Alkanes
- This page defines alkanes as simple organic compounds made exclusively of carbon and hydrogen with single bonds. It describes their saturated characteristics and presents methane, ethane, and propane as examples. The text explains the homologous series principle, where each compound varies by a CH2 unit, and mentions the general formula for alkanes (CnH2n + 2), which aids in organizing organic chemistry and predicting properties of related compounds.
- 12.3: Branched-Chain Alkanes
- This page discusses the structure of alkanes, focusing on butane (C4H10) and its branched isomer isobutane, illustrating isomerism. It explains that lower alkanes like methane, ethane, and propane lack isomers due to simpler structures. The text also presents pentane and its isomers, isopentane and neopentane, emphasizing their unique properties despite having the same molecular formula. Straight-chain alkanes are noted, with butane referred to as n-butane, though the prefix is often omitted.
- 12.4: Condensed Structural and Line-Angle Formulas
- This page describes three types of chemical formulas for organic compounds: molecular formulas indicate atom types and numbers; structural formulas show atom arrangement and bonding; and condensed formulas simplify this by aligning hydrogen with carbon atoms. Line-angle formulas further condense the representation by suggesting carbon at line ends and corners, with hydrogen atoms implicitly included to fulfill carbon's bonding needs.
- 12.5: IUPAC Nomenclature
- This page explains the IUPAC naming system for alkanes, detailing key concepts like the longest continuous chain (LCC) principle, alkyl group nomenclature, and numbering rules for substituents. It highlights the complexities of naming isomers as carbon count increases and offers simplified rules and examples for practical application, aiming to ensure that each unique compound is assigned a distinct name.
- 12.6: Physical Properties of Alkanes
- This page covers the physical properties of alkanes, emphasizing their nonpolarity, low density, and boiling point trends with molar mass. It notes their insolubility in water and effectiveness as solvents for low-polarity substances. The significance of alkanes extends to petroleum products, lipid studies, and cell membranes, along with safety concerns regarding fire hazards related to gas leaks.
- 12.7: Chemical Properties of Alkanes
- This page discusses alkanes, nonpolar hydrocarbons known for their low reactivity and classified as paraffins. They primarily undergo two reactions: combustion, which produces carbon dioxide, water, and heat (with incomplete combustion potentially generating carbon monoxide), and halogenation, where they react with chlorine or bromine in the presence of ultraviolet light or heat, resulting in halogenated compounds.
- 12.8: Halogenated Hydrocarbons
- This page discusses halogenated hydrocarbons, formed through halogen-alkane reactions, and their naming conventions. It lists examples and uses, emphasizing health risks associated with chlorinated hydrocarbons, particularly toxicity and cancer concerns. The text also addresses the effects of chlorofluorocarbons on the ozone layer and highlights the transition to safer alternatives.
- 12.9: Cycloalkanes
- This page explains cycloalkanes, cyclic hydrocarbons made of carbon rings, starting with cyclopropane (C3H6), formerly used as an anesthetic but now avoided due to explosiveness. Cycloalkanes are named with "cyclo-" as a prefix, and share properties with noncyclic alkanes; cyclopentane and cyclohexane are notably stable. Cyclopropane exhibits strain in its ring structure due to small bond angles.
- 12.E: Organic Chemistry- Alkanes and Halogenated Hydrocarbons (Exercises)
- This page offers a comprehensive review of organic and inorganic compounds, especially alkanes, covering their classification, properties, and IUPAC nomenclature. It discusses straight-chain vs branched-chain alkanes, physical properties, reactivity with halogens, and the importance of substituents.
- 12.S: Organic Chemistry- Alkanes and Halogenated Hydrocarbons (Summary)
- This page discusses organic and inorganic chemistry with a focus on alkanes, which are saturated hydrocarbons represented by the formula CnH2n+2. The chapter explains their structures, isomers starting from C4H10, and the IUPAC naming system. Alkanes are nonpolar, insoluble in water, and generally unreactive, yet they can undergo combustion and react with halogens to form alkyl halides. Cycloalkanes, which are ring-structured hydrocarbons, are also introduced.