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12.1 – Organic CompoundsIdentify properties characteristic of organic or inorganic compounds.
Organic CompoundsOrganic 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 compoundsMany 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.
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
• 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.
As butane (C4H10) rotates, sometimes theline 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:
Formulas of CycloalkanesTable 12.4 Formulas of Some Common CycloalkanesName BLANK BLANK BLANKCyclopropane Cyclobutane Cyclopentane Cyclohexane
Ball-and-Stick Model BLANK BLANK BLANKThree carbons single-bonded to each other in a triangular pattern, with each carbon single-bonded to 2 hydrogens.
The ball and stick model shows four carbons single-bonded to each other in a square pattern, with each carbon single-
bonded to 2 hydrogens.
The ball and stick model shows five carbons single-bonded to each other in a pentagonal pattern, with each carbon single-bonded to 2 hydrogens.
The ball and stick model shows six carbons single-bonded to each other in a hexagonal pattern, with each carbon
single-bonded to 2 hydrogens.
Condensed Structural Formula BLANK BLANK BLANKThe condensed structural formula shows a triangular ring of three C H 2 molecules.
The condensed structural formula shows a square ring of four C H 2 molecules.
The condensed structural formula shows a pentagonal ring of five C H 2
molecules.
The condensed structural formula shows a hexagonal ring of six C H 2 molecules.
Line-Angle Structural Formula BLANK BLANK BLANKThe line-angle structural formula is a triangle. The line-angle structural formula shows a
square.The line-angle structural formula shows
a pentagon. The line-angle structural formula shows a hexagon.
Solution Draw three possible structural isomers of pentane (C5H12).
Structural Isomers of
C5H12
Structural Isomers of C5H12 Structural Isomers of C5H12
Structural Isomers of C5H12
CondensedThe first condensed structural formula is a straight chain of single-bonded molecules as follows. C H 3, C H 2, C H 2, C H 2, C H 3. The second condensed structural formula is a branched chain as follows. C H 3, C H single-bonded to C H 3 above,
C H 2, C H 3. The third condensed structural formula is a central C single-bonded to four C H 3 molecules above, below, rightward, and leftward.
Line-AngleThe line-angle structural formula shows a zigzag line made of 4 segments forming 3 angles. The line-angle structural formula shows a zigzag of 3 segments forming 2 angles, with
a fourth segment rising vertically from the first angle.The line-angle structural formula shows 2 rising and falling line segments with 2 segments rising diagonally right and left from the angle.
Substituents in Alkanes• When CH3 branches off of a carbon chain, it’s called an alkyl group
• When a halogen atom (Group 17) is attached to a carbon chain, it is named as a halo group with the terms –fluoro, -chloro, -bromo, -iodobased on which element it is.
Substituents and Alkyl Groups Table 12.5 Formulas and Names of Some Common Substituents
FormulaName
Formula, C H 3, single bond. name, methyl.Formula, straight chain, C H 3, C H 2, single bond. name, ethyl.
BLANK BLANK
FormulaName
Formula, straight chain, C H 3, C H 2, C H 2, single bond. name, propyl.
Formula, branched chain, C H 3, C H with single bond above, C
H 3. name, isopropyl. BLANK BLANK
FormulaName
Formula, straight chain, C H 3, C H 2, C H 2, C H 2, single bond. name, butyl.
Formula, branched chain, C H 3, C H single-bonded to C H 3 above, C H 2, single bond. name, isobutyl.
Formula, C H 3, C H with single bond above, C H 2, C H 3. name, secondary butyl.
Formula, central C with single bond above and three C H 3 molecules below, rightward, and leftward. name, tertiary butyl.
FormulaName
Formula, F, single bond. name, fluoro. Formula, F, single bond. name, fluoro. Formula, B r, single bond. name, bromo. Formula, I, single bond. name, iodo.
• are alakanes with a halogen atom that replaces a hydrogen atom.
• are named by putting the substituents in alphabetical order.
• have the halo group numbered according to the carbon where it is attached to the alkane.
Examples of Haloalkanes
BLANK BLANK BLANK BLANK
Formulastraight chain, C H 3, C l straight chain, C H 3, C H 2, B r Branched chain, C H 3, C H single-bonded to an F above A central C single-bonded to C l above and three C H 3 molecules below, rightward, and leftward
• have higher boiling points than the straight-chain alkanes with the same number of carbon atoms.
• have limited rotation of carbon bonds; they maintain their rigid structure and can be stacked closely together, which gives them many points of contact and attractions to each other.
We can compare the boiling points of straight-chain alkanes, branched-chain alkanes, and cycloalkanes.Table 12.6 Comparison of Boiling Points of Alkanes and Cycloalkanes with Five Carbons
Formula Name Boiling Point (°C)
Straight-Chain Alkane BLANK BLANKStraight chain alkanes. condensed structural formula, C H 3, C H 2, C H 2, C H 2, C H 3
Pentane 36
Branched-Chain Alkanes BLANK BLANKBranched chain alkanes. condensed structural formula, C H 3, C H single-bonded to C H 3, C H 2, C H 3
2-Methylbutane 28
Central C single-bonded to four C H 3 molecules
Dimethylpropane 10
Cycloalkane BLANK BLANKline-angle structural formula, a pentagonal ring
Chemistry Link to the Environment: Fragrant Alkenes (1 of 2)
The odors you associate with lemons, oranges, roses, and lavender come from the volatile compounds that are synthesized by the plants that produce these flowers and fruits.Often these compounds contain double or triple bonds or ring structures; they are unsaturated.
12.7 – Addition Reactions for AlkenesDraw the condensed or line-angle structural formulas and give the names of the organic products of addition reactions of alkenes. Draw a condensed structural formula for a section of a polymer.
Hydration• In hydration, an alkene reactions with water (H-OH). A hydrogen atom (H-) from water forms a bond with one carbon atom in the double bond, and the oxygen atom in (-OH) forms a bond with the other carbon.
• The reaction is catalyzed by a strong acid, such as H2SO4, written as H+.
• Hydration is used to prepare alcohols, which have the hydroxyl (-OH) functional group.
Hydration – Markovnikov’s Rule• When water is added to an asymmetrical alkene, the H is added to the carbon with more H’s already attached. The –OH bonds to the other carbon.
• A polymer is a large molecule that consists of small repeating units called monomers.
• Many of these polymers are produced by addition reactions of alkenes.
• In the past hundred years, the plastics industry has made synthetic polymers such as those in carpeting, plastic wrap, nonstick pans, artificial joins, heart valves, and rain gear.
Benzene• In 1825, Michael Faraday isolated a hydrocarbon called benzene.
• Benzene is:– An aromatic compound– A ring of six C atoms, each bonded to one H atom– A flat ring structure draw with three alternating double bonds.– Represented by two structures, because the electrons are shared
equally among all the C atoms– Represented by a line-angle structural formula using a cirl in the
• The common name xylene is used for the isomers of dimethylbenzene.
• If three or more substituents are attached to the benzene ring, they are numbered in the direction to give the lowest set of numbers and then named alphabetically.