Organic Chemistry: Hydrocarbons

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Introduction to Organic Chemistry: Hydrocarbons Chapter 12 Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved Chapter 12 12.1 – Organic Compounds 12.2 – Alkanes 12.3 – Alkanes with Substituents 12.4 – Properties of Alkanes 12.5 – Alkenes and Alkynes 12.6 – Cis-Trans Isomers 12.7 – Addition Reactions for Alkenes 12.8 – Aromatic Compounds Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved 12.1 – Organic Compounds Identify properties characteristic of organic or inorganic compounds. Organic Compounds Organic chemistry is the study of carbon compounds. An organic compound • Always contains carbon and hydrogen atoms • May also contain other nonmetals such as oxygen, nitrogen, phosphorus, or a halogen. • Organic compounds are found in: • Gasoline, medicines, shampoos, plastics, and perfumes • Carbohydrates, fats, and proteins Functional Groups • Organic compounds are organized by their functional groups (groups of atoms bonded in a specific way). • Compounds that contain the same functional groups have similar physical and chemical properties. • The identification of functional groups allows us to classify organic compounds according to their structure, to name compounds within each family, and to predict their chemical reactions. Organic vs. Inorganic • In chemistry, molecules are classified as Organic or Inorganic. • Inorganic compounds are (quite expansively) anything that is not organic. • Organic and Inorganic compounds have different properties. – Organic compounds: Have low melting and boiling points. Are flammable and undergo combustion. Are not soluble in water. – Inorganic compounds Many inorganic compounds have high melting and boiling points. Inorganic compounds that are ionic are usually soluble in water, and most do not burn in air. Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved Practice Identify each characteristic as most typical of compounds that are inorganic or organic. A. It has a high melting point. B. It is not soluble in water. C. It contains carbon and hydrogen atoms. D. It has the formula MgCl2. E. It burns easily in air. Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved Representations of Carbon Compounds • Hydrocarbons are organic compounds that consist of only carbon and hydrogen. – In organic molecules, every carbon atom has four bonds. – In methane (CH4), the carbon atom forms an octet by sharing its four valence electrons with four hydrogen atoms. Three-dimensional and two-dimensional representations of methane: a) space-filling model, b) ball-and-stick model, c) wedge-dash model, d) expanded structural formula, and e) condensed structural formula Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved Representations of Carbon Compounds • In ethane (C2H6), each tetrahedral carbon forms three covalent bonds to hydrogen and one to the other carbon. Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved Alkanes Alkanes • are formed by a continuous chain of carbon atoms. • are named using the IUPAC (International Union of Pure and Applied Chemistry) system. • have names that end in ane. • use Greek prefixes to name carbon chains with five or more carbon atoms. Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved Study Check In the butane molecule (C4H10), predict the shape around each carbon atom. H H H H H C C C C H H H H H Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved Chapter 12 12.1 – Organic Compounds 12.2 – Alkanes 12.3 – Alkanes with Substituents 12.4 – Properties of Alkanes 12.5 – Alkenes and Alkynes 12.6 – Cis-Trans Isomers 12.7 – Addition Reactions for Alkenes 12.8 – Aromatic Compounds Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved 12.2 - Alkanes Write the IUPAC names and draw the condensed or line-angle structural formulas for alkanes and cycloalkanes. Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved Alkanes • More than 90% of the compounds in the world are organic compounds. • The larger number of carbon compounds is possible because the covalent bonds between carbon atoms (C-C) is very strong, allowing carbon atoms to form long, stable chains. Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved Alkanes • The alkanes are a type of hydrocarbon in which the carbon atoms are connected only by single bonds. – Alkanes are formed by a continuous chain of carbon atoms. – The names of alkanes and in –ane. Such names are part of the IUPAC system (International Union of Pure and Applied Chemistry) used by chemists to name organic chemistry. – Alkanes made of carbon chains are named based on how many carbons make up the chain. – One of the most common uses of alkanes is as fuels. Methane, propane, octane, and hexane are all alkanes used as fuels. Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved IUPAC Names of Alkanes Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved Line-Angle Structural Formulas A simplified structure of organic molecules • is called the line-angle structural formula. • shows a zigzag line in which carbon atoms are represented as the ends of each line and as corners. Carbon atoms • at the end are bonded to three hydrogen atoms. • in the middle are bonded to two hydrogen atoms. Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved Condensed formula and Line-angle formula • Pentane Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved Condensed formula and Line-angle formula • Draw the condensed structural formula and name the molecule: Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved Guide to Drawing Structural Formulas for Alkanes Step 1: Draw the carbon chain. Step 2: Draw the expanded structural formula by adding the hydrogen atoms using single bonds to each of the carbon atoms. Step 3: Draw the condensed structural formula by combining the H atoms with each C atom. Step 4: Draw the line-angle structural formula as a zigzag line in which the ends and corners represent C atoms. Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved Drawing Expanded, Condensed, and Line- Angle Structural Formulas (1 of 3) Draw the expanded, condensed, and line-angle structural formula for pentane. Step 1: Draw the carbon chain. A molecule of pentane has five carbon atoms in a continuous chain. Step 2: Draw the expanded structural formula by adding the hydrogen atoms, using single bonds to each of the carbon atoms. Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved Drawing Expanded, Condensed, and Line- Angle Structural Formulas (2 of 3) Draw the expanded, condensed, and line-angle structural formula for pentane. Step 3: Draw the condensed structural formula by combining the H atoms with each C atom. Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved Drawing Expanded, Condensed, and Line- Angle Structural Formulas (3 of 3) Draw the expanded, condensed, and line-angle structural formula for pentane. Step 4: Draw the line-angle structural formula as a zigzag line in which the ends and corners represent C atoms. Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved Conformations of Alkanes • Single bonds can spin and rotate. • Thus different arrangements, known as conformations, occur during the rotation about a single bond. • http://symmetry.otterbein.edu/gallery/index.html Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved Structural Formulas: C4H10 As butane (C4H10) rotates, sometimes the line up in front of each other, and at other times they are opposite each other. Butane can be drawn using a variety of two-dimensional condensed structural formulas: Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved Structural Formulas: C4H10 Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved Cycloalkanes Hydrocarbons can also form into circles or rings called: cycloalkanes • have two fewer hydrogen atoms than the open chain form. • are named by using the prefix cyclo before the name of the alkane chain with the same number of carbon atoms. Copyright © 2016, 2013, 2010 Pearson Education, Inc. All Rights Reserved Formulas of Cycloalkanes Table 12.4 Formulas of Some Common Cycloalkanes Name BLANK BLANK BLANK Cyclopropane Cyclobutane Cyclopentane Cyclohexane Ball-and-Stick Model BLANK BLANK BLANK Three carbons single-bonded to each other in a triangular pattern, The ball and stick model shows four The ball and stick model shows five The ball and stick model shows six with each carbon single-bonded to 2 hydrogens. carbons single-bonded to each other in a carbons single-bonded to each other in carbons single-bonded to each other in square pattern, with each carbon single- a pentagonal pattern, with each carbon a hexagonal pattern, with each carbon single-bonded to 2 hydrogens. bonded to 2 hydrogens. single-bonded to 2 hydrogens. Condensed Structural Formula BLANK BLANK BLANK The condensed structural formula shows a triangular ring of three C The condensed structural formula shows The condensed structural formula The condensed structural formula H 2 molecules. a square ring of four C H 2 molecules. shows a pentagonal ring of five C H 2 shows a hexagonal ring of six C H 2 molecules. molecules. Line-Angle Structural Formula BLANK BLANK BLANK The
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