Introductory Chemistry, 2nd Edition Nivaldo Tro

Introductory Chemistry, 2nd Edition Nivaldo Tro

Organic Chemistry The Nature of LightIts Wave Nature Light is one of the forms of energy. Light is a form of electromagnetic radiation. Electromagnetic radiation is made of waves. Electromagnetic radiation moves through space like waves move across the surface of a pond 2 Tro's "Introductory Chemistry", Chapter 9 Electromagnetic Waves Every wave has four characteristics that determine its properties: wave speed, height (amplitude), length, number of wave peaks that pass in a given time. All electromagnetic waves move through space at the same, constant speed. 3.00 x 108 meters per second in a vacuum = The speed of light, c.

3 Tro's "Introductory Chemistry", Chapter 9 Characterizing Waves The amplitude is the height of the wave. The distance from node to crest. Or node to trough. The amplitude is a measure of how intense the light isthe larger the amplitude, the brighter the light. The wavelength () is a measure of the distance covered by the wave. The distance from one crest to the next. Or the distance from one trough to the next, or the distance between alternate nodes. Usually measured in nanometers. 1 nm = 1 x 10-9 m 4 Tro's "Introductory Chemistry", Chapter 9 Characterizing Waves The frequency () is the number of waves that pass a point in a given period of time.

The number of waves = number of cycles. Units are hertz (Hz), or cycles/s = s-1. 1 Hz = 1 s-1 The total energy is proportional to the amplitude and frequency of the waves. The larger the wave amplitude, the more force it has. The more frequently the waves strike, the more total force there is. 5 Tro's "Introductory Chemistry", Chapter 9 Low Frequency Wave High Frequency Wave The Electromagnetic Spectrum Light passed through a prism is separated into all its colors. This is called a continuous spectrum. The color of the light is determined by its wavelength. 7

Electromagnetic Spectrum 8 Tro's "Introductory Chemistry", Chapter 9 Types of Electromagnetic Radiation Classified by the Wavelength Radiowaves = > 0.01 m. Low frequency and energy. Microwaves = 10-4m < < 10-2 m. Infrared (IR) = 8 x 10-7 < < 10-5 m. Visible = 4 x 10-7 < < 8 x 10-7 m. ROYGBIV. Ultraviolet (UV) = 10-8 < < 4 x 10-7 m. X-rays = 10-10 < < 10-8 m. Gamma rays = < 10-10. High frequency and energy. 9 Tro's "Introductory Chemistry", Chapter 9 The Electromagnetic Spectrum and Photon Energy Short wavelength light has photons with high energy. High frequency light has photons with high

energy. Radiowave photons have the lowest energy. Gamma ray photons have the highest energy. High-energy electromagnetic radiation can potentially damage biological molecules. Ionizing radiation. 10 Tro's "Introductory Chemistry", Chapter 9 What Is Organic Chemistry? Organic chemistry is a branch of chemistry that focuses on compounds that contain carbon. Except CO, CO2, carbonates, and carbides. Even though organic compounds only contain a few elements, the unique ways carbon atoms can attach together to form molecules leads to millions of different organic compounds. 11 The Chemistry of Life Life as we know it is because of organic chemistry. Organic molecules can be very large and complex; this allows the complex functions of the cells to occur.

When chemists tried to classify compounds in the 1700s, they found vast differences between the compounds found in living and nonliving things. 12 Classifying Pure Substances, the Modern Way Pure substance Compound Element Is is a carbon compound and not CO, CO2, a carbonate, or carbide? Is it shiny, malleable, and ductile; does it conduct heat and electricity? Yes Metal

Some Metalloid No Nonmetal Yes Organic No Inorganic 13 Whats Special About Organic Compounds? Organic compounds tend to be molecular. Mainly composed of just six nonmetallic elements. C, H, O, N, S, and P. Compounds found in all three states. Solids, liquids, and gases. Solids tend to have low melting points. Solubility in water varies depending on which of the other elements are attached to C and how many there are.

CH3OH is miscible with water; C10H21OH is insoluble. 14 Whats So Special About Carbon? Carbon atoms can do some unique things that other atoms cannot. Carbon can bond to as many as four other atoms. Bonds to carbon are very strong and nonreactive. Carbon atoms can attach together in long chains. Carbon atoms can attach together to form rings. Carbon atoms can form single, double, or triple bonds. 15 Bond Energies and Reactivities Bond CC SS SiSi NN OO Bond Energy 347 kJ 214 kJ 213 kJ 159 kJ

138 kJ Compound Reactivity H3CCH3 HSSH Nonreactive in air Extremely reactive H3SiSiH3 Spontaneously combusts in air H2NNH2 HOOH Extremely reactive Very reactive 16 Hydrocarbons Compounds that contain only carbon and hydrogen Two classes: Aliphatic and aromatic 17

The Petroleum Feedstock Most hydrocarbons come from petroleum Composed mostly of alkanes and aromatic hydrocarbons 18 19 Purification via fractional distillation 20 Hydrocarbons Hydrocarbons contain only C and H. Two classes of hydrocarbons: saturated or unsaturated. Insoluble in water. No polar bonds to attract water molecules. May be chains or rings. Ring molecules have less H than chain so that the ends can join. Chains may be straight or branched. Rings may be aliphatic or aromatic. 21 Uses of Hydrocarbons Number of

C atoms 14 57 618 1224 1850 50+ 50+ State gas Gas Major uses heating and cooking fuel liquids, solvents, Liquids (low boiling) gasoline liquids Liquids gasoline jet fuel; camp fuel,

liquids Liquids stove fuel diesel fuel, Liquids liquids, lubricants, (high boiling) heating oil petroleum jelly, jelly, petroleum Solids solids paraffin wax wax paraffin Saturated Hydrocarbons A saturated hydrocarbon has all CC single bonds. It is saturated with hydrogens. Saturated hydrocarbons are called alkanes. Chain alkanes have the general formula CnH2n+2. Chains may be straight or branched. Normal isomer is the straight chain. Ring alkanes have two fewer Hs per ring than the corresponding chain isomer.

23 Unsaturated Hydrocarbons Unsaturated hydrocarbons have one or more C=C double bonds, CC triple bonds, or aromatic rings. Unsaturated hydrocarbons that contain C=C are called alkenes. The general formula of a monounsaturated chain alkene is CnH2n. Remove two more Hs for each additional unsaturation. Unsaturated hydrocarbons that contain CC are called alkynes. The general formula of a monounsaturated chain alkyne is CnH2n2 . Remove four more Hs for each additional unsaturation. 24 Some Unsaturated Hydrocarbons H3C H C H3 C CH3

C H C CH3 H3 C C C CH3 HC H2C CH3 C CH3 H2C H2C H2 C C

CH2 H2C C H2 H C C H2 H2 C C H2 C CH2 C H2 H2C C H2 CH2

H2 C CH2 CH2 25 Aromatic Hydrocarbons Aromatic hydrocarbons contain a ring structure that seems to have C=C, but doesnt behave that way. The most prevalent example is benzene. C6H6. Other compounds have the benzene ring with other groups substituted for some of the Hs. H C CH HC CH HC CH C H

HC CH HC CH CH 26 Hydrocarbons 27 Types of Hydrocarbons H2 C C H C CH 2 3 H3C C C CH 3

H H CH3 C C 2C CH CH3 C 2 H3C H3C C H H C 2 CH 3 C H2 H2 C C H C C2 H H2 C

CH22 HC CH H2 C H H22C CH2 C CH C 2 C H2 H2 alkanes alkenes Alkynes 28 Formulas Molecular formulas just tell you what kinds of atoms are in the molecule, but they dont tell you how they are attached. Structural formulas show you the attachment pattern in the molecule. Models not only show you the attachment pattern, but give you an idea about the shape of the molecule.

29 Carbon Skeleton Formulas A.k.a. line-angle formulas. Used very often with ring structures. Each angle, and its beginning and end represent a C atom. H omitted on C. Included on functional groups. Multiple bonds indicated. Double line is double bond; triple line is triple bond. 30 Name Structural formula H Methane H H Ethane Propane Butane Pentane

H H H C H H C H H H H H C H H C

C C C H H H H C H H H H H H H

C H H H C H H Hexane C H C C H H H H

H H C C H H H H H H H H C C

C C C C H H H H H H H H Condensed formula CH4 Boiling

point -162 C CH3CH3 -89 C CH3CH2CH3 -42 C CH3CH2CH2CH3 0 C CH3CH2CH2CH2CH3 36 C CH3CH2CH2CH2CH2CH3 69 C 31 Write the Structural and Condensed Formula for the n-Alkane C8H18. Connect the C atoms in a row. Carbon skeleton.

Add H to complete four bonds on each C. Middle C gets 2 Hs. End C gets 3 Hs. C C C C C C C C H H H H H H H H H C C C C

C C C C H H H H H H H H H The condensed formula has the CH3CH2CH2CH2CH2CH2CH2CH3 H attached to each C written directly after it. 32 PracticeWrite a Complete Structural Formula for C7H16. 33 PracticeWrite a Complete Structural Formula for C7H16, Continued. H H H H H H H H

C C C C C C C H H H H H H H H 34 Alkanes Also know as paraffins.

Aliphatic, saturated. General formula CnH2n+2 for chains. Very unreactive. CH3 groups at ends of chains; CH2 groups in the middle. Chains may be straight or branched. n-Alkane = straight chain. 35 Structural Isomers Isomers are molecules with the same molecular formula, but different arrangements of the atoms. Different chemical and physical properties. Structural isomers are isomers in which the atoms are attached differently. Different bonding pattern. Structural isomers have different physical properties. Structural isomers may give different products in a reaction, though they undergo the same types of reactions. 36 Structural Isomers of C4H10 Butane, BP = 0 C H H H H H C C C C H

H H H H Isobutane, BP = -12 C H H H H C C C H H H H C H H 37 Possible Structural Isomers Carbon Molecular Possible content formula isomers 4 C4H10 2 5 C5H12 3 6 C6H14 5

7 C7H16 9 8 C8H18 18 9 C9H20 35 10 C10H22 75 38 ExampleWrite the Structural Formula and Carbon Skeleton Formula for C6H14. Start by connecting the carbons in a line. C C C C C C C C C C C CC CC C C CC CC

C C C C C C C C C Determine the C skeleton of the other isomers. 39 ExampleWrite the Structural Formula and Carbon Skeleton Formula for C6H14, Continued. Fill in the Hs to give each C four bonds. H H H

H H H H C C C C C C C H H H H H H H

H H H H H C C C C H C C H C H C H H H H H

H C H C H CC C C H C H C H H H H H H C C C C H C C H H

H C H H C H H H H H H H H H C C C H H H H H H C CC C

H H C CC C C C H H H C H H C H H H H AlkanesPhysical Properties Nonpolar molecules, intermolecular attractions due to induced dipoles. Both boiling points and melting points generally increase as the size of the molecule increases. Insoluble in water, commonly used as nonpolar solvents. Less dense than water, density increases with size. 42

Physical Properties of Solubility: Hydrocarbons Tend to be insoluble in water Can be used for protective coatings Good preservative for reactive metals Density: Tend to have lower densities than water 0.6 g/mL 0.8 g/mL 43 Physical Properties of nAlkanes Name Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane Undecane Dodecane Tridecane

Formula Molar Mass BP, C MP, C Density, g/mL CH4 16 -162 -183 0.47 CH3CH3 30 -89 -183 0.57 CH3CH2CH3 44 -42 -188 0.50 CH3CH2CH2CH3 58 0 -138 0.58 CH3(CH2)3CH3 72 36 -130 0.56 CH3(CH2)4CH3 86 69

-95 0.66 CH3(CH2)5CH3 100 98 -91 0.68 CH3(CH2)6CH3 114 126 -57 0.70 CH3(CH2)7CH3 128 151 -54 0.72 CH3(CH2)8CH3 142 174 -30 0.74 CH3(CH2)9CH3 156 196 -26 0.75 CH3(CH2)10CH3 170

216 -10 0.76 CH3(CH2)11CH3 184 235 -5 0.76 44 n-Alkane Boiling and Melting Points 500 400 Temperature, C 300 200 BP, n-alkane 100 MP, n-alkane 0 -100 -200 -300 0

100 200 300 400 500 Molecular w eight Tro's Introductory Chemistry, Chapter 18 45 Naming Each name consists of three parts: 1. Prefix. Indicates position, number, and type of branches. Indicates position, number, and type of each functional group. 2. Parent.

Indicates the length of the longest carbon chain or ring. 3. Suffix. Indicates the type of hydrocarbon. -ane, -ene, -yne Certain functional groups. 46 Naming Alkanes 1. Find the longest, continuous carbon chain. 2. Number the chain from the end closest to a branch. If first branches equal distance, use the next in. 3. Name branches as alkyl groups. Locate each branch by preceding its name with the carbon number on the chain. 4. List branches alphabetically. Do not count n-, sec-, t-, but count iso. 5. Use prefix if more than one of the same group is present. di-, tri-, tetra-, penta-, hexa-. Do not count in alphabetizing. 47 BranchesAlkyl Groups

H H C H CH3-, METHYL H H H C C H H CH3CH2-, ETHYL H H H H C C C H H H CH3CH2CH2-, PROPYL H CH3 H C C H H (CH3)2CH-, ISOPROPYL 48 More Alkyl Groups H H H H H C C C C

H H H H CH3CH2CH2CH2-, n-BUTYL H H CH3 H C C C H H H CH3CH2(CH3)CH-, sec-BUTYL H H C H (CH3)2CHCH2-, ISOBUTYL CH3 H C C H H CH3 H 3C C CH3 (CH3)3C-, tert- BUTYL 49

Examples of Naming Alkanes 2-methylpentane 3-isopropyl-2,2-dimethylhexane H H H H H H H C C C C C

H CH3 H H H H H CH3 H H H H C C C C

C C H CH3 CH H H H CH3 CH3 H 50 Example 18.6Name the Alkane. CH3CHCH2CHCH3 CH3 CH3

1. Find the longest, continuous C chain and use it to determine the base name. CH3CHCH2CHCH3 CH3 CH3 Since the longest chain has 5 Cs, the base name is pentane. 51 Example 18.6Name the Alkane, Continued. CH3CHCH2CHCH3 CH3 CH3 2. Identify the substituent branches. CH3CHCH2CHCH3 CH3 CH3 There are two substituents. Both are one C chains called methyl. 52

Example 18.6Name the Alkane, Continued. 3. Number the chain from the end closest to a substituent branch. If first substituents equidistant from end, go to next substituent in. Then assign numbers to each substituent based on the number of the main chain C to which its attached. 1 2 3 4 5 CH3CHCH2CHCH3 Both substituents are equidistant from the end. CH3 2 CH3 4

53 Example 18.6Name the Alkane, Continued. 4. Write the name in the following order: a. Substituent number of first alphabetical substituent followed by dash. b. Substituent name of first alphabetical substituent followed by dash. If its the last substituent listed, no dash. Use prefixes to indicate multiple identical substituents. c. Repeat for other substituents alphabetically. d. Name of main chain. CH3CHCH2CHCH3 CH3 2 2,4 dimethylpentane CH3 4 54 PracticeName the Following: CH3 CH3 CHCHCH2 CH3 CH2 CH3 55

PracticeName the Following, Continued: CH3 CH3 CHCHCH2 CH3 CH2 CH3 3-ethyl-2-methylpentane 56 Drawing Structural Formulas Draw and number the base chain carbon skeleton. Add the carbon skeletons of each substituent on the appropriate main chain C. Add in required Hs. 4-ethyl-2-methylhexane C C C C C C 1 2 3 4 5 6 C C C C C C C C C CH3 CH CH2 CH CH2 CH3 CH3

H2C CH3 57 PracticeDraw the Structural Formula of 4-isopropyl-2-methylheptane. 58 PracticeDraw the Structural Formula of 4-isopropyl-2-methylheptane, Continued. CH3 CH CH2 CH CH2 CH2 CH3 CH3 HC CH3 CH3 59 Alkenes Also known as olefins. Aliphatic, unsaturated. C=C double bonds.

Formula for one double bond = CnH2n. Subtract two Hs from alkane for each double bond. Trigonal shape around C. Flat. Much more reactive than alkanes. Polyunsaturated = many double bonds. 60 n1Alkenes Alkenes Ethene = ethylene H H H H H C C H

Propene H C C CH3 62 Physical Properties of Alkenes Molar Mass BP, C Density, g/cm 3 28 -104 0.52 Name Ethene Formula CH2=CH2 Propene CH2=CHCH3 42 -47 0.59

1-butene CH2=CHCH2CH3 56 -6 0.59 1-pentene CH2=CH(CH2)2CH3 70 30 0.64 1-hexene CH2=CH(CH2)3CH3 84 64

0.68 1-heptene CH2=CH(CH2)4CH3 98 93 0.70 1-octene CH2=CH(CH2)5CH3 112 122 0.72 1-nonene CH2=CH(CH2)6CH3 126 146

0.73 63 Alkynes Also known as acetylenes. Aliphatic, unsaturated. CC triple bond. Formula for one triple bond = CnH2n-2. Subtract four Hs from alkane for each triple bond. Linear shape. More reactive than alkenes. 64 n1Alkynes 65 Alkynes Ethyne = acetylene H C C H

Propyne H C C CH3 66 Physical Properties of Alkynes Name Formula Molar mass BP, C Density, g/cm 3 Ethyne CHCH 28 -104 0.52 Propyne

CHCCH3 42 -47 0.59 1-butyne CHCCH2CH3 56 -6 0.59 1-pentyne CHC(CH2)2CH3 70 30 0.64 1-hexyne

CHC(CH2)3CH3 84 64 0.68 1-heptyne CHC(CH2)4CH3 98 93 0.70 1-octyne CHC(CH2)5CH3 112 122 0.72

1-nonyne CHC(CH2)6CH3 126 146 0.73 1-decyne CHC(CH2)7CH3 140 171 0.74 67 Naming Alkenes and Alkynes Find longest chain containing multiple bond. Alkene takes precedence over alkyne. Change suffix on main name from -ane to -ene for base name of alkene, or to yne for the base name of the alkyne. Number chain from end closest to multiple bond.

Number in front of main name indicates first carbon of multiple bond. 68 Examples of Naming Alkenes 2-methyl-1-pentene H 3-isopropyl-2,2-dimethyl-3-hexene H H H H C C C C C H

CH3 H H H H CH3 C C C H CH3 CH H H

H C C C H H H CH3 CH3 69 H Examples of Naming Alkynes 3-methyl-1-pentyne H 4-isopropyl-5,5-dimethyl-2-hexyne H C

H H H C C C CH3 H H C H CH3 H C C C

H CH3 CH H H C CH3 CH3 C C H 70 H Name the Alkene 1. Find the longest, continuous C chain that contains the double bond and use it to determine the base name. H2 C CH3 H3 C CH

C CH CH3 H2 C CH3 Since the longest chain with the double bond has six Cs, the base name is hexene. 71 Name the Alkene, Continued 2. Identify the substituent branches. H2C CH3 H3 C CH C CH CH3 H2C CH3 There are two substituents. One is a one-C chain, called methyl and the other one is a two-C chain, called ethyl. 72 Name the Alkene, Continued 3. Number the chain from the end closest to the double bond. Then assign numbers to each substituent based on the number of the main chain C to which its attached. 3

H2C CH3 4 H3 C CH C CH CH3 4 3 H2C CH3 5 2 1 6 73 Name the Alkene, Continued 4. Write the name in the following order: a. b. Substituent number of first alphabetical substituent. Substituent name of first alphabetical substituent.

Use prefixes to indicate multiple identical substituents. c. Repeat for other substituents. d. Number of first C in double bond; name of main chain. 3 H2C CH3 4 H3 C CH C CH CH3 4 3 H2C CH3 5 3ethyl4methyl2hexene 2 1 6 74

Reactions of Hydrocarbons All hydrocarbons undergo combustion. Combustion is always exothermic. About 90% of U.S. energy generated by combustion. 2 CH3CH2CH2CH3(g) + 13 O2(g) 8 CO2(g) + 10 H2O(g) CH3CH=CHCH3(g) + 6 O2(g) 4 CO2(g) + 4 H2O(g) 2 CH3CCCH3(g) + 11 O2(g) 8 CO2(g) + 6 H2O(g) 75 Chemical Energy Burning hydrocarbons releases heat and light energy. Combustion. Alkane + oxygen carbon dioxide + water. Larger alkane, more heat released. Alkane Methane Ethane Propane Butane Pentane Heat of combustion Molecular (kcal/mole) formula

CH4 213 C2H6 373 C3H8 531 C4H10 687 C5H12 845 76 Other Alkane Reactions Substitution. Replace H with a halogen atom. Cl or Br. Initiated by addition of energy in the form of heat or ultraviolet light. To start breaking bonds. Generally get multiple products with multiple substitutions. H H H C C H + Cl Cl H H heat or

UV light H Cl H C C H + H Cl H H 77 Predict the Products and Balance the Equations. h CH3CH3 + Br2 CH3 H3C CH3 CH3 C H2 CH3 + O2 H Isooctane C8H18 78

Predict the Products and Balance the Equations, Continued. h CH3CH3 + Br2 CH3CH2Br + HBr CH3 2 H3C CH3 CH3 C H2 CH3 + 25 O2 16 CO2 + 18 H2O H Isooctane C8H18 79 Other Alkene and Alkyne Reactions Addition reactions. Adding a molecule across the multiple bond.

Hydrogenation = adding H2. Converts unsaturated molecule to saturated. Alkene or alkyne + H2 alkane. H H H H C C C C H + H2 H + 2 H2 H H H

H C C H H H H C C H H H H 80 Reactions of Alkenes H2 C

CH2 + Combustion 3 O2 2 CO2 + 2 H2O Addition Reactions Hydrogenation Hydration Hydrohalogenation H2C H2C H2 C CH2 CH2

CH2 + + + H2 H2 O HCl H3C CH3 H OH C H2 CH2 H Cl

C H2 CH2 Addition Reactions HH CC HH C CC HCl + ++ H-Cl 22 CH CH333 CH HH H Cl H H H

H HH HH CC CH CH3 33 CC ClCl H PracticePredict the Products. H2C H2C H2C H2C H2 C C H2 H2 C

C H2 CH CH CH CH + H2 + HCl PracticePredict the Products, Continued. H H2 H2C H2C H2C H2C C

C H2 H2 C C H2 CH CH CH CH + + H2 HCl H2C H2C C 2

C H2 H C H C H H H2C H2 C H C H2C C H C H2 H Cl

Aromatics Benzene HC Resonance hybrid. Does not react like alkenes. HC H C C H CH HC CH HC H C C H

Reactions are generally substitutions for H. Br HC HC H C C H CH CH + Br2 FeBr3 HC CH HC CH

C H + HBr 85 CH CH Resonance Hybrid The true structure of benzene is a resonance hybrid of two structures. 86 Naming Monosubstituted Benzene Derivatives (Name of substituent) benzene. Halogen substituent = change ending to o. CH2CH2CH3 F propylbenzene

fluorobenzene Or name of a common derivative. CH3 NH2 toluene aniline OH phenol HC CH2 styrene 87 Naming Benzene as a Substituent When the benzene ring is not the base name, it is called a phenyl group. H2 C CH CH2

CH CH2 CH3 4-phenyl-1-hexene 88 Naming Disubstituted Benzene Derivatives Number the ring starting at attachment for first substituent, then move toward second. Order substituents alphabetically. Use di- if both substituents are the same. CH3 F 3 2 1 Br 1-bromo-3-fluorobenzene 1 2 CH3

1,2-dimethylbenzene 89 Naming Disubstituted Benzene Derivatives, Continued Alternatively, use relative position prefixes: ortho- = 1,2; meta- = 1,3; para- = 1,4. CH3 Cl CH3 CH3 Cl 2-chlorotoluene ortho-chlorotoluene o-chlorotoluene 3-chlorotoluene meta-chlorotoluene m-chlorotoluene Cl 4-chlorotoluene para-chlorotoluene

p-chlorotoluene 90 PracticeName the Following: F Br Br Cl 91 PracticeName the Following, Continued: F Br Br Cl 1-chloro-4-fluorobenzene 1,3-dibromobenzene or meta-dibromobenzene or m-dibromobenzene 92 Functional Groups

Other organic compounds are hydrocarbons in which functional groups have been substituted for hydrogens. A functional group is a group of atoms that show a characteristic influence on the properties of the molecule. Generally, the reactions that a compound will perform are determined by what functional groups it has. Since the kind of hydrocarbon chain is irrelevant to the reactions, it may be indicated by the general symbol R. R group CH3OH Functional group 93 Functional Groups, Continued 94 Alcohols ROH. Ethanol = CH3CH2OH. Grain alcohol = fermentation of sugars. Alcoholic beverages. Proof number = 2x percentage of alcohol.

Gasohol. Isopropyl alcohol = (CH3)2CHOH. 2-propanol. Rubbing alcohol. Poisonous. Methanol = CH3OH. Wood alcohol = thermolysis of wood. Paint solvent. Poisonous. Naming Alcohols Find the main chain that contains OH. Unless C=O present. Number main chain from end closest to OH. Give base name -ol ending and place number of C on chain where OH attached in front. Name as hydroxy group if other higher precedence group present. 1 CH3 2 CH2 OH CH3

3 4 5 6 CH C CH CH2 CH2CH3 4-ethyl-4-methyl-3-hex-5-enol 96 PracticeName the Following: H3C H2 C H3C C H2 H C C H H3C CH3 C

CH3 OH 97 PracticeName the Following, Continued: H3C 6 H3C H2 C 5 4 C H2 CH3 H C C H

1 3 H3C 2 C CH3 OH 3-isopropyl-2-methyl-2-hexanol 98 PracticeDraw a Structural Formula for 3-ethyl-2,4-dimethyl-2-pent-4-enol. 99 Ethers ROR. Ether = diethyl ether = CH3CH2OCH2CH3. Anesthetic. To name ethers, name each alkyl group

attached to the O, then add the word ether to the end. 100 PracticeName the Following: H2 C H3 C O C H2 H C CH3 CH3 101 PracticeName the Following, Continued: H2 C H3 C O

C H2 H C CH3 CH3 Isopropyl propyl ether 102 Aldehydes and Ketones Contain the carbonyl group. Aldehydes = at least 1 side H. Ketones = both sides R groups. Many aldehydes and ketones have pleasant tastes and aromas. Some are pheromones. Formaldehyde = H2C=O. Pungent gas.

Formalin = a preservative. Wood smoke, carcinogenic. Acetone = CH3C(=O)CH3. O C Formaldehyde Acetone Nail-polish remover. 103 Aldehyde Odors and Flavors Butanal = butter. O C CH2CH2CH3 H O O Vanillin = vanilla.HO

H HO Benzaldehyde = almonds. O H C Cinnamaldehyde = cinnamon. O H C C H C H 104 Ketone Odors and Flavors Acetophenone = pistachio. O C

H3C Carvone = spearmint. H3C O C CH2 CH3 Ionone = raspberries. HC CH O 3 3 H C C C CH3 H CH3 Muscone

= musk. O CH 3 105 Naming Aldehydes and Ketone Make part of main chain. Number from end closest to carbonyl. Precedence over OH group. For aldehyde, change ending to -al. Always position 1, no number necessary. For ketone, change ending to -one. Indicate position on chain with number in front of base name. OH O C H CH2CH2CH2 4-hydroxybutanal OH O

CH3 CH2 CH C CH CH2 4-hydroxy-3-hex-1-enone 106 Carboxylic Acids RCOOH. Sour tasting. Weak acids. Citric acid. O O CH2 C OH HO C C OH

CH2 C OH O Found in citrus fruit. Ethanoic acid = acetic acid. Vinegar. O CH3 C OH Methanoic acid = formic acid. Insect bites and stings. O H C OH 107 Carboxylic Acids, Continued Made by the oxidation of aldehydes and alcohols. O C

O H C oxidation OH OH on the end of the chain. Always on main chain. Has highest precedence. C of group always C1. benzaldehyde OH H3C CH2 ethanol benzoic acid O

oxidation H3C C OH ethanoic acid Position not indicated in name. Change ending to -oic acid. 108 Naming Acids Main chain always contains COOH group. C of COOH group always Cl. Position not indicated in name. Give base name -oic acid ending. CH3 HO C OH C H3 C

C O H2 3-hydroxy-3-methylpentanoic acid 109 Esters RCOOR. Sweet odor. Made by reacting carboxylic acid with an alcohol. RaCOOH + RbOH RaCOORb + H2O Name alkyl group from alcohol, then acid name with -ate ending. Precedence over carbonyls, but not carboxylic acid. Number from end with ester group. O C OH O C CH3

O Aspirin 110 Naming Esters Main chain always contains COOR group. Unless acid group also present. C of COOR group on C1. Position not indicated in name. Start by naming R group as alkyl group. No position number. Always listed first, even if other groups on chain. Change ending on base name to -oate. CH3 O C CH3 O CH CH3 methyl-4-isopropylbenzoate 111

Naming Esters, Continued 112 Amines N containing organic molecules. Very bad smelling. Form when proteins decompose. Organic bases. Name alkyl groups attached to the N, then add -amine to the end. H3C NH2 H3C NH CH2 H3 C Ethylamine

H 2NCH 2CH 2CH 2CH 2NH2 Putrescine CH2 H 2NCH 2CH 2CH 2CH 2CH 2NH 2 Ethylmethylamine Cadaverine 113 Identify the Functional Groups in Each. O CH3CH2COOCH3. O O (CH3CH2)2NH. O O C OH CH3CHCHCH2CHO. OCH3

115 Identify the Functional Groups in Each, Continued. O CH3CH2COOCH3. O O Ester H3C (CH3CH2)2NH. Amine H3C C O C H2 H2 C

N H H2 C CH3 2 H C O Ketone and ether O O CH3CHCHCH2HCHO. H Double bond H C C C C H and aldehyde 3 O

CH3 C Ester OH Acid, aromatic ring, ether OCH3 Polymers 117 Macromolecules Polymers are very large molecules made by repeatedly linking together small molecules. Monomers. Natural. Modified natural polymers. Synthetic. Plastics, elastomers (rubber), fabrics, adhesives.

Composites. Additives such as graphite, glass, metallic flakes. 118 Natural Polymers Polysaccharides. Cellulose (cotton). Starch. Proteins. Nucleic acids (DNA). Natural latex rubber, etc. Shellac. Amber, lignin, pine rosin. Asphalt, tar. 119 Modified Natural Polymers Cellulose acetate. Rayon.

Film. Vulcanized rubber. Gun cotton. Celluloid. Ping-pong balls. Gutta percha. Fill space for root canal. Casein. Buttons, moldings, adhesives. 120 Polymers Polymerization The process of linking the monomer units together. Two process are addition polymerization and condensation polymerization. Monomers may link head to tail, head to head, or tail to tail. Head-to-tail linking is most common. Regular pattern gives stronger attractions between chains than random arrangements. 122

Addition Polymerization Monomers add to the growing chain in such a manner that all the atoms in the original monomer wind up in the chain. No other side products formed, no atoms eliminated. First monomer must open to start reaction. Done with heat or addition of an initiator. Chain reaction. Each added unit ready to add another. 123 Addition Polymerization, Continued initiator H H C H H etc.

C Cl H H C C initiator H H H C C Cl H

H H + H C C Cl H H Cl H H H H H

C C C C + Cl H Cl H H H C Cl H C H

H H H H C C C C Cl H Cl H H H

H H H H C C C C C C Cl H Cl H

Cl H Condensation Polymerization Monomer units are joined by removing small molecules from the combining units. Polyesters, polyamides lose water. No initiator needed. Chain reaction. Each monomer has two reactive ends, so chain can grow in two directions. 125 Condensation Polymerization, Continued + HO HO + O

O C C O O C C OH + HO O CH2 CH2 CH2 OH CH2 +

OH H2O 126 Plastics Material capable of being molded or shaped. Round, hard balls; thin, flexible threads; intricate molds; or flat sheets. Molar mass 10,000 to 1,000,000 amu. Many are in glass or amorphous solid state. Solid that has semi-fluid characteristics. Glass transition temperature. Do not melt like an ice cube. 127 Plastic Characteristics

Transparent or translucent. Chemical resistance. Thermal and electrical insulators. Low density. Varying strengths. Kevlar. Mold or extrude. Elasticity. Regain original shape if quick stress applied. Foamed. Tend to soften when heated. Rather than quickly melt. 128 Synthetic Polymers Polyethylene HDPE LDPE Polypropylene Polyvinyl chloride Polyesters polyethylene terephthalate Polyamides nylon Kevlar

Polyethylene Terephthalate (PET) Condensation copolymer of ethylene glycol + terephthalic acid. A polyester. H 1 O H Transparent. O C C C O H High-impact strength. H Nonreactive with acid and atmospheric gases. Doesnt stretch. Used for soda bottles, Dacron, Mylar. O C

130 High Density Polyethylene (HDPE) Addition polymer with linear chains. 2 Opaque. Denser than LDPE. Mechanically stronger than LDPE. H H More rigid than LDPE. More crystalline. C C Higher heat resistance than LDPE. Nonreactive to acids and bases. Absorbs oils and softens. H H Oxidizes on exposure to air and sunlight.

Subject to cracking. Used for containers, caps, bullet-proof vests, synthetic ice. 131 Poly Vinyl Chloride (PVC) Addition polymer. 3 Transparent to opaque. Flame resistant. H Cl Low heat resistance. Good chemical resistance. High-impact strength. C C Quite rigid. Many additives used to modify properties. H H Plasticizer adds flexibility. Used in food wrap, pipes, flooring and wall

covering, toys, hoses, auto trim, squeeze tubes, and appliance housings. 132 Low Density Polyethylene (LDPE) 4 Addition polymer with branched chains. Lower density, strength, heat resistance (100125 C), and rigidity than HDPE. Used in food, trash, and grocery bags as well as in electrical wire insulation. H H C C H H 133

Polypropylene (PP) Addition polymer. Opaque. High-stretching strength. High heat resistance (170 C). Excellent chemical resistance. Flexed almost indefinitely without tearing. Smooth surface with high luster. Used in carpets and upholstery; chemical resistant pipes, containers, and tanks; margarine tubs; and medicine bottles. 5 H CH3 C

C H H 134 Polystyrene (PS) Addition polymer. H Low-impact resistance. Fair strength and stiffness. C Poor chemical resistance. H Transparent, glassy, sparkling clarity. Moderate heat resistance (90 C). Model cars, computer housing, Styrofoam, clear drinking cups, and hard-molded parts.

6 H C 135 Acrylics Polymethylmethacrylate, PMMA. Low-impact resistance. O H C OCH3 Good strength and stiffness. Excellent transparency. C C Excellent scratch resistance. H

CH3 Moderate heat resistance. Addition polymer of methyl methacrylate. Uses include Plexiglas, Lucite, lighting fixtures, lenses, fiber optic filament, appliance faceplates, decorative signs, and paints. Also, reduces oil viscosity. 136 Polycarbonates (PC) Excellent physical properties. Excellent toughness. O CH3 Very good heat resistance. O C O C Fair chemical resistance. CH3

Transparent. Condensation copolymer of Bisphenol A and phosgene. Lexan, Calibre , Makrolon , Panlite . Used in equipment housings, exterior auto parts, outdoor light fixtures, non-auto vehicle windows, structural parts, medical supply parts, scratch-resistant coatings, eye wear, bulletproof glass, and DVDs. 137 Nylon Condensation copolymer of a diamine with a diacid. Polyamides. Nylon 6,6 made by condensing 1,6hexandiamine, H2N(CH2)6 NH2, with hexandioic acid, HOOC(CH2)4COOH. Good physical properties. Effected by moisture. Very good heat resistance. Excellent chemical resistance. Excellent wear resistance. O HN (CH2)6 NH C

O (CH2)4 C 138

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