2. Organic Nomenclature

3. Organic Compounds Organic Compounds - any covalently bonded compound containing carbon (except carbonates and oxides)

4. Organic Compounds  Contain carbon  Have covalent bonds  Have low melting points  Have low boiling points  Burn in air (oxygen)  Are soluble in nonpolar solvents  Form large molecules

5. General Characteristics of Organic Molecules Organic molecules exhibit three different types of hybridization at the carbon center: –sp 3 hybridized carbons for tetrahedral geometries; –sp 2 hybridized carbons for trigonal planar geometries; and –sp hybridized carbons for linear geometries.

6. Stabilities of Organic Molecules Carbon forms very strong bonds between H, O, N, and halogens. Carbon also forms strong bonds with itself. Therefore, C can form stable long chain or ring structures. Bond strength increases from single to double to triple bond. Bond length decreases in the same direction.

7. Hydrocarbons Hydrocarbons - Organic compounds that contain only carbon & hydrogen Alkanes - contain only single covalent bonds Alkenes - contain one or more carbon - carbon double bond Alkynes - contain one or more carbon-carbon triple bond

8. Saturated & Unsaturated Hydrocarbons Saturated hydrocarbons – contain only single carbon-carbon bonds (alkanes) Unsaturated hydrocarbons – contain double carbon-carbon bonds (alkenes) or triple carbon-carbon (alkynes) bonds

9. Formulas Alkanes = C n H 2n+2 Alkenes = C n H 2n Alkynes = C n H 2n-2

10. Nomenclature Must memorize prefixes To name, look at the formula for the hydrocarbon Determine if it is an alkane, alkene, or alkyne Use the prefix for the number of carbons Add ending (ane, ene, yne) Prefix # of carbon atoms Meth-1 Eth-2 Prop-3 But-4 Pent-5 Hex-6 Hept-7 Oct-8 Non-9 Dec-10

11. Example Name C 3 H 8 This falls under the equation C n H 2n+2 Therefore it is an alkane Since n=3 we will use the prefix prop Since it is an alkane we will use the ending ane propane

12. Alkanes Contain C and H only Contain single bonds C-C Have 4 bonds to every carbon (C) atom Are nonpolar

13. Complete Structural Formulas Show the bonds between each of the atoms H H  H  C  HH C H  H H CH 4, methane

14. Drawing structures: it’s all good On a test, choose a method that shows all Hs 2-butene This is called the “condensed structure” CH 3 CH=CHCH 3 Using brackets can also shorten some formulas: CH 3 (CH 2 ) 4 CH 3 vs. CH 3 CH 2 CH 2 CH 2 CH 2 CH 3

15. More Alkanes H HCondensed Structural Formulas H C C HCH 3 CH 3 H HEthane H H H H C C C HCH 3 CH 2 CH 3 H H H Propane

16. IUPAC Names Name# carbons Structural Formula Methane1CH 4 Ethane2CH 3 CH 3 Propane3CH 3 CH 2 CH 3 Butane4CH 3 CH 2 CH 2 CH 3 Pentane5CH 3 CH 2 CH 2 CH 2 CH 3

17. Naming: common vs. IUPAC Common names used in the 1800’s are still used for some compounds today: Acetylene AcetoneFormic acid The International Union of Pure and Applied Chemistry (IUPAC) was established in 1900s Frequent revisions to nomenclature Systematic method allows an infinite number of compounds to be named given a few rules

18. IUPAC NAMES Name # carbons Structural Formula Hexane 6 CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 Heptane 7 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 Octane 8 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 Nonane 9 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 Decane 10 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3

19. Learning Check Alk1 A. What is the condensed formula for H H H H H C C C C H H H H H B. What is its molecular formula? C. What is its name?

20. Branched Alkanes CH 3 CH 3 CHCH 3 methyl groups CH 3 CH 3 CH 3 CHCH 2 CHCH 3

21. Alkyl Groups Branches on carbon chains H H CCH 3 methyl H H H H C C CH 3 CH 2 ethyl H H

22. Naming Branched Alkanes CH 3 methyl branch CH 3 CH 2 CH 2 CHCH 2 CH 3 6 5 4 3 2 1Count

23. Naming Branched Alkanes CH 3 methyl branch CH 3 CH 2 CH 2 CHCH 2 CH 3 6 5 4 3 2 1Count 3-Methylhexane on third C CH 3 six carbon chain group

24. Naming side chains Names are made up of: side chains, root Root is the longest possible HC chain Must contain multiple bonds if present Add -yl to get name of side chain Common side chains include: CH 3 - methyl CH 3 CH 2 - ethyl CH 3 CH 2 CH 2 - propyl (CH 3 ) 2 CH- isopropyl 2,3-dimethylpentane CH 3 CH 3 CH 3 CH 3 “iso” (branched) is not an IUPAC convention Br- (bromo), Cl- (chloro), F- (fluoro), I- (iodo)

25. ene Naming side chains Example: use the rules to name: Rule 1: choose the correct ending

26. ene Rule 2: longest carbon chain Naming side chains

27. Alkenes and Alkynes – Alkenes are hydrocarbons with at least one double carbon to carbon bond. To show the presence of the double bond, the –ane suffix from the alkane name is changed to –ene. – The alkenes are unsaturated with respect to hydrogen This means it does not have the maximum number of hydrogen atoms as it would if it were an alkane (a saturated hydrocarbon).

28. – Naming is similar to naming alkanes except: The longest continuous chain must contain the double bond. The base name now ends in –ene. The carbons are numbered so as to keep the number for the double bond as low as possible. The base name is given a number which identifies the location of the double bond. – An alkyne is a hydrocarbon with at least one carbon to carbon triple bond. – Naming an alkyne is similar to the alkenes, except the base name ends in –yne.

29. Alkenes  Carbon-carbon double bonds  Names end in -ene H 2 C=CH 2 ethene (ethylene) H 2 C=CH-CH 3 propene (propylene) cyclohexene

30. Alkynes  Carbon-carbon triple bonds  Names end in -yne HC  CHethyne(acetylene) HC  C-CH 3 propyne

31. Naming Alkenes and Alkynes When the carbon chain has 4 or more C atoms, number the chain to give the lowest number to the double or triple bond. 1 2 3 4 CH 2 =CHCH 2 CH 3 1-butene CH 3 CH=CHCH 3 2-butene CH 3 C  CCH 3 2-butyne

32. Numbering carbons Q- draw pentene A- Where’s the bond? We number C atoms Thus, naming compounds with multiple bonds is more complex than previously indicated Only if 2+ possibilities exist, are #s needed Always give double bond the lowest number Q - Name these Ethene 3-nonyne 2-butene C2H4C2H4 1-pentene

33. Multiple multiple bonds Give 1 st bond (1 st point of difference) lowest # include di, tri, tetra, penta, etc. before ene/yne Comma between #s, hyphen between #-letter You do not need to know ene + yne 2,3-heptadiene 2,4,6-nonatriyne CH 3 CH 2 CH 2 CH=C=CH 2 2-butyne 1,2-hexadiene 1,2,4-pentatriene

34. Cyclic structures Cyclic structures are circular Have “cyclo” in name Benzene is not a cyclic structure cyclopentane Q- Draw these (note: carbons in a double bond should be consecutive- 1 and 2, 5 and 6, etc.): cyclobutene 1,3-cyclopentadiene cyclopropane

35. 1-hexene ene Rule 3: attach prefix (according to # of C) Naming side chains

36. Rule 4: Assign numbers to each carbon 1-hexene Naming side chains

37. Rule 4: Assign numbers to each carbon 1-hexene Naming side chains

38. Rule 5: Determine name for side chains 1-hexene Naming side chains ethyl methyl

39. 2-ethyl-4,4-dimethyl-1-hexene Naming side chains ethyl methyl Rule 6: attach name of branches

40. Learning Check HA3 Write the IUPAC name for each of the following unsaturated compounds: A.CH 3 CH 2 C  CCH 3 CH 3 B. CH 3 C=CHCH 3 C.

41. Solutions HA3 Write the IUPAC name for each of the following unsaturated compounds: A.CH 3 CH 2 CH=CHCH 3 2-pentene CH 3 B. CH 3 C=CHCH 3 C. 2-methyl-2-butene 3-methylcyclopentene

42. Numbering priority 1. functional groups 2. double and triple bonds 3. substituents

43. Once all groups have been numbered, place them in alphabetical order in the final compounds name. Numbers are separated by commas Names and numbers are separated by dashes. Use mathematical prefixes for multiple substituent's.

44. Often times you will find shorter branches of carbons off of the longest (main or parent) chain. These branches are known as alkyl groups, branches or substituents. They are named using the same prefixes as before but using -yl as a suffix on the name.

45. Naming Branched Chain Alkanes 1. Find the longest continuous chain of hydrocarbon (remember that they may bend around corners). This is your parent chain. 2. Number the parent chain beginning from the end closest to the first branch.

46. 3. Identify the alkyl groups and the carbon number on the parent chain they are attached to. 4. List the alkyl groups in alphabetical order and the number where the attachment occurs. (Separate numbers from words with hyphens). 5. Finally, list the parent name.

47. Ex: CH 3 CH 2 CHClCH 2 CH=CHCHBrCH 3 2-bromo-5-chloro-3-octene

48. Learning Check Alk4 A. CH 3 CH 3 CH 3 CHCH 2 CHCH 3 B. CH 3 CH 3 CH 3 CH 2 CHCH 2 CCH 2 CH 3 CH 3

49. Solution Alk4 A. CH 3 CH 3 CH 3 CHCH 2 CHCH 3 2,4-dimethylpentane B. CH 3 CH 3 CH 3 CH 2 CHCH 2 CCH 2 CH 3 CH 3 3,3,5-trimethylheptane

50. Learning Check Alk5 Write a condensed structure for A. 3,4-dimethylheptane B. 2,2-dimethyloctane

51. Solution Alk5 A. 3,4-dimethylheptane CH 3 CH 3 CH 2 CHCHCH 2 CH 2 CH 3 CH 3 B.2,2-dimethyloctane CH 3 CH 3 CCH 2 CH 2 CH 2 CH 2 CH 2 CH 3 CH 3

52. Cycloalkanes Cyclopropane CH 2 CH 2 CH 2 Cyclobutane CH 2 CH 2 CH 2

53. More Cycloalkanes Cyclopentane CH 2 CH 2 CH 2 CH 2 Cyclohexane CH 2

54. Naming Cycloalkanes with Side Groups Number of Naming side groups 1.Side group name goes in front of the cycloalkane name. 2.Number the ring in the direction that gives the lowest numbers to the side groups.

55. Cycloalkanes with Side Groups

56. Learning Check Alk8

57. Solution Alk8

58. Aromatic Compounds and Benzene Aromatic compounds contain benzene. Benzene, C 6 H 6, is represented as a six carbon ring with 3 double bonds. Two possible can be drawn to show benzene in this form.

59. Benzene Structure The structures for benzene can also be written as a single structure where the alternating double bonds are written as a circle within the ring. Benzene structure

60. Aromatic Compounds in Nature and Health Many aromatic compounds are common in nature and in medicine.

61. Naming Aromatic Compounds Aromatic compounds are named with benzene as the parent chain. One side group is named in front of the name benzene. methylbenzenechlorobenzene (toluene)

62. Naming Aromatic Compounds When two groups are attached to benzene, the ring is numbered to give the lower numbers to the side groups. The prefixes ortho (1,2), meta (1,3-) and para (1,4-) are also used.

63. Some Common Names Some substituted benzene rings also use a common name. Then naming with additional more side groups uses the ortho-, meta-, para- system.

64. Learning Check Alk9 Select the names for each structure: 1. Chlorocyclohexane 2. Chlorobenzene 3. 1-chlorobenzene 1. Meta-methyltoluene 2. Meta-dimethylbenzene 3. 1,3-dimethylbenzene

65. Solution Alk9 Select the names for each structure: 2. Chlorobenzene 1. Meta-methyltoluene 2. Meta-dimethylbenzene 3. 1,3-dimethylbenzene

66. Learning Check Alk10 Write the structural formulas for each of the following: A. 1,3-dichlorobenzene B. Ortho-chlorotoluene

67. Solution Alk10 Write the structural formulas for each of the following: A. 1,3-dichlorobenzene B. Ortho-chlorotoluene

68. Isomers

69. Types of isomerism Isomerism Structural isomerismStereoisomerism Geometric isomerismOptical isomerism

70. Isomers- structural  Same molecular formula  Same number and types of atoms  Different arrangement of atoms

71. isomers Isomers- all the possible spatial arrangements for a given hydrocarbon. Follow these steps= 1. start with the longest straight chain. 2. shorten the chain by one carbon, and add that extra carbon as a methyl group in all the possible positions starting from the left and moving right.

72. 3. check each time to make sure the names don’t repeat. 4. shorten the chain by 2 carbons. Add each carbon separately as a methyl to all the possible places. Keep your numbering system correct. Then add the 2 carbons as an ethyl group following the same pattern. Ex: Try heptane and octane

73. Examples of Isomers The formula C 4 H 10 has two different structures CH 3 CH 3 CH 2 CH 2 CH 3 CH 3 CHCH 3 Butane 2-methylpropane When a CH 3 is is used to form a branch, it makes a new isomer of C 4 H 10.

74. Decane Draw 4 isomers of decane H H C H H C H H C H H C H H C H H C H H C H H C H H C H H C H H c c c c c c c c c c c c c c c c c c c c c c c c c c c c c c c c c c c c c c c c

75. Learning Check Alk6 Write 3 isomers of C 5 H 12 and name each.

76. Solution Alk6 CH 3 CH 2 CH 2 CH 2 CH 3 pentane CH 3 CH 3 CHCH 2 CH 3 2-methylbutane CH 3 CH 3 CCH 3 2,2-dimethylpropane CH 3

77. Learning Check Alk7 Write the structural formulas of 3 isomers that have the formula C 5 H 12. Name each.

78. Solution Alk7 Write the structural formulas of 3 isomers that have the formula C 5 H 12. Name each. CH 3 CH 2 CH 2 CH 2 CH 3 pentane CH 3 CH 3 CH 3 CHCH 2 CH 3 CH 3 CCH 3 CH 3 2-methylbutane 2,2-dimethylpropane

79. Cis trans isomers This also occurs around the double or triple bonds in straight chains. Ex: C 4 H 8 has 4 isomers

80. Cis and Trans Isomers  Double bond is fixed  Cis/trans Isomers are possible CH 3 CH 3 CH 3 CH = CH CH = CH cis trans CH 3

81. Look at these models Cis -2-butene Trans – 2 - butene

82. Two isomers are not interchangeable. Carbon 2 & 3 joined by double bond. No free rotation. Bonds would have to be broken and reformed. +270 kJ mol -1 energy needed to break this bond. Insufficient energy available at room temperature.

83. cis... Different names needed to identify isomers. Substituent groups on the same side of double bond. Cis -2-butene

84. ...and trans. “trans” means other side or cross over e.g. trans Atlantic, transplant, trans…..! Substituents on opposite sides of double bond. Trans-2- butene

85. Different compounds- different properties.

86. 1-butene Cis-2-butene Trans-2-butene 2-methylpropene ( isobutene) Cis is also called the Z isomer for the German word zusammen = together Trans are also called the E isomer for the word entegen = opposite.

87. Draw all the isomers For – C 5 H 10 and C 6 H 12 and name them include all cis /trans isomers

88. Organic Chemistry: Functional Groups

89. Functional Groups  Part of an organic molecule where chemical reactions take place  Composed of an atom or group of atoms  Replace a H in the corresponding alkane  Provide a way to classify organic compounds

90. Functional Groups Class Functional group Alcohol R – OH R – OH Ether R — O — R’ R — O — R’ Aldehyde O || || R — C — H R — C — H Ketone O || || R — C — R’ R — C — R’ Carboxylic acid O || || — C — OH — C — OH Ester O || || R — C — O — R’ R — C — O — R’ Amine R’ R’ | R — N — R’’ R — N — R’’

91. Some Types of Functional Groups Haloalkane-F, -Cl, -Br CH 3 Cl Alcohol-OH CH 3 OH Ether-O- CH 3 -O-CH 3 Aldehyde Ketone

92. More Functional Groups Carboxylic acid -COOH CH 3 COOH Ester -COO- CH 3 COOCH 3 Amine -NH 2 CH 3 NH 2 Amide -CONH 2 CH 3 CONH 2

93. Haloalkanes An alkane in which one or more H atoms is replaced with a halogen (F, Cl, Br, or I) CH 3 Br1-bromomethane Br (methyl bromide) CH 3 CH 2 CHCH 3 2-bromobutane Cl chlorocyclobutane

94. Organic Compounds Containing Halogens Hydrocarbons: Basic Concepts Topic 27 Topic 27 Any organic compound that contains a halogen substituent is called a halocarbon. If you replace any of the hydrogen atoms in an alkane with a halogen atom, you form an alkyl halide.

95. Hydrocarbons: Basic Concepts Topic 27 Topic 27 An alkyl halide is an organic compound containing a halogen atom covalently bonded to an aliphatic carbon atom. The first four halogens— fluorine, chlorine, bromine, and iodine—are found in many organic compounds. Organic Compounds Containing Halogens

96. Hydrocarbons: Basic Concepts Topic 27 Topic 27 For example, chloromethane is the alkyl halide formed when a chlorine atom replaces one of methane’s four hydrogen atoms. Organic Compounds Containing Halogens

97. Hydrocarbons: Basic Concepts Topic 27 Topic 27 An aryl halide is an organic compound containing a halogen atom bonded to a benzene ring or other aromatic group. The structural formula for an aryl halide is created by first drawing the aromatic structure and then replacing its hydrogen atoms with the halogen atoms specified. Organic Compounds Containing Halogens

98. Learning Check HA1 Name the following:

99. Solution HA1 Name the following: bromocyclopentane 1,3-dichlorocyclohexane

100. Substituents List other attached atoms or group in alphabetical order Br = bromo, Cl = chloro Cl Br CH 3 CHCH 2 CHCH 2 CH 2 CH 3 4-bromo-2-chloroheptane

101. Learning Check HA2 The name of this compound is: Cl CH 3 CH 3 CH 2 CHCH 2 CHCH 3 1) 2,4-dimethylhexane 2) 3-chloro-5-methylhexane 3) 4-chloro-2-methylhexane

102. Solution HA2 The name of this compound is: Cl CH 3 CH 3 CH 2 CHCH 2 CHCH 3 3) 4-chloro-2-methylhexane

103. Haloalkanes as Anesthetics Halothane (Fluothane) F Cl F C C Br F H Fluothane is a haloalkane that is widely used as an anesthetic, which is a compound that decreases the ability of the nerve cells to conduct pain.

104. Ozone Layer Ozone layer Stratosphere (10-30 miles Above Earth)

105. Chlorofuorocarbons (CFCs and the Ozone Layer  ozone O 3 layer absorbs most of the sun’s harmful radiation.  CFCs - chlorofluorocarbons - are depleting that ozone layer.  CFCs are used as Freons in refrigeration, air conditioning, and foam insulation.  Their use in spray cans is no longer allowed.

106. Alcohols Alcohols have a OH group attached to a C somewhere along the chain. The ending changes to “ol” If there are 2 OH groups the are referred to as a “diol” The OH group has to be identified using the IUPAC numbering system Ex: CH 2 ClCHOHCHClCH 3 1,3-dichloro-2-butanol

107. Alcohols Hydrocarbons: Basic Concepts Topic 27 Topic 27 An oxygen-hydrogen group covalently bonded to a carbon atom is called a hydroxyl group (—OH). group replaces a hydrogen atom of a hydrocarbon is called an alcohol. An organic compound in which a hydroxyl The general formula for an alcohol is ROH.

108. Naming Alcohols A carbon compound that contain -OH (hydroxyl) group In IUPAC name, the -e in alkane name is replaced with -ol. CH 4 methane CH 3 OH methanol (methyl alcohol) CH 3 CH 3 ethane CH 3 CH 2 OH ethanol (ethyl alcohol )

109. Ethanol CH 3 CH 2 OH Acts as a depressant Kills or disables more people than any other drug 12-15 mg/dL ethanol metabolized by a social drinkers in one hour 30 mg/dL ethanol metabolized by an alcoholic in one hour.

110. Alcohol in Some Products % EthanolProduct 50%Whiskey, rum, brandy 40%Flavoring extracts 15-25%Listerine, Nyquil, Scope 12%Wine, Dristan, Cepacol 3-9%Beer, Lavoris

111. More Names of Alcohols IUPAC names for longer chains number the chain from the end nearest the -OH group. CH 3 CH 2 CH 2 OH1-propanol OH CH 3 CHCH 3 2-propanol CH 3 OH CH 3 CHCH 2 CH 2 CHCH 3 5-methyl-2-hexanol

112. Some Typical Alcohols OH “rubbing alcohol”CH 3 CHCH 3 2-propanol (isopropyl alcohol) antifreeze HO-CH 2 -CH 2 -OH 1,2-ethanediol (ethylene glycol) OH glycerolHO-CH 2 -CH-CH 2 OH Anti-freeze

113. Learning Check Al 2 Name the following alcohols: A. OH CH 3 CHCHCH 2 CH 3 CH 3 OH B.

114. Solution Al 2 Name the following alcohols: A. OH 3-methyl-2-pentanol CH 3 CHCHCH 2 CH 3 CH 3 OH B. cyclobutanol

115. Reactions of Alcohols Combustion CH 3 OH + 2O 2 CO 2 + 2H 2 O + Heat Dehydration H OH H +, heat H-C-C-H H-C=C-H + H 2 O H H alcohol alkene

116. Aldehydes and Ketones In an aldehyde, an H atom is attached to a carbonyl group Ocarbonyl group  CH 3 -C-H In a ketone, two carbon groups are attached to a carbonyl group Ocarbonyl group  CH 3 -C-CH 3

117. aldehydes Aldehydes contain a CHO attached to the end of a carbon chain The C has a double bonded O and a single bonded H attached to it. Since it is at the end of a chain there is no need to number. The ending changes to “al” Ex: CH 3 CHICH 2 CH 2 CHICHO 2,5-diiodohexanal

118. Naming Aldehydes IUPAC Replace the -e in the alkane name -al Common Add aldehyde to the prefixes form (1C), acet (2C), propion(3), and butry(4C) O O O   II H-C-H CH 3 -C-HCH 3 CH 2 C-H methanal ethanal propanal (formaldehyde) (acetaldehyde) (propionaldehyde)

119. Aldehydes as Flavorings

120. Glucose is an aldehyde

121. Ketones Ketones have a C=O bond embedded within a chain. The IUPAC system of numbering applies here and the “e” of the chain gets replaced with a “one” ending O ║ Ex: CH 3 CH 2 CCH 2 CH 2 CH 2 CH 2 CH 3 3-octanone

122. Naming Ketones In the IUPAC name, the -e in the alkane name is replaced with -one In the common name, add the word ketone after naming the alkyl groups attached to the carbonyl group O  II CH 3 -C-CH 3 CH 3 -C-CH 2 -CH 3 2- Propanone 2-Butanone (Dimethyl ketone) (Ethyl methyl ketone)

123. Ketones O O  Butter flavorCH 3 -C-C-CH 3 butanedione O  Clove flavorCH 3 -C-CH 2 CH 2 CH 2 CH 2 CH 3 2-heptanone

124. Fructose is a Ketone

125. Ketones as Hormones

126. Learning Check AK 1 Classify each as an aldehyde (1), ketone (2) or neither(3). O II A. CH 3 CH 2 CCH 3 B. CH 3 -O-CH 3 CH 3 O  C. CH 3 -C-CH 2 CHD. CH 3

127. Solution AK 1 Classify each as an aldehyde (1), ketone (2) or neither(3). O II A. CH 3 CH 2 CCH 3 2 B. CH 3 -O-CH 3 3 CH 3 O  C. CH 3 -C-CH 2 CH 1 D. 2 CH 3

128. Learning Check AK 2 Name the following O  A. CH 3 CH 2 CCH 3 B. CH 3 O II C. CH 3 -C-CH 2 CH CH 3

129. Solution AK 2 O  A. CH 3 CH 2 CCH 3 B. 2-butanone (ethyl methyl ketone) CH 3 O  C. CH 3 -C-CH 2 CH cyclohexanone CH 3 2,2-dimethylbutanal

130. Learning Check AK 3 Draw the structural formulas for each: A. 3-Methylpentanal B. 2,3-Dichloropropanal C. 3-Methyl-2-butanone

131. Solution AK 3 Draw the structural formulas for each: CH 3 O  A. 4-MethylpentanalCH 3 CHCHCH 2 CH Br O  B. 2,3-Dibromopropanal Br-CH 2 CHCH O  C. 3-Methyl-2-butanoneCH 3 CHCCH 3 CH 3

132. ethers Have an O atom within the carbon chain itself. In other words C-O-C. Components of the chain on both sides of the O have to be named. Ethers have the general formula ROR′. No numbering system is needed since the chain is broken. The name remains the same just add the ending ether

133. Ethers The simplest ether is one in which oxygen is bonded to two methyl groups. Note the relationship between methanol and methyl ether in the following diagram.

134. Ethers Contain an -O- between two carbon groups Simple ethers named from -yl names of the attached groups and adding ether. CH 3 -O-CH 3 dimethyl ether CH 3 -O-CH 2 CH 3 ethyl methyl ether

135. Ex: CH 3 OCH 2 CH 2 CH 2 CH 2 CH 3 Methyl-n-pentyl ether The “n” signifies that the carbons are in a straight chain with no branches.

136. Ethers as Anesthetics Anesthetics inhibit pain signals to the brain CH 3 CH 2 -O-CH 2 CH 3 used for over a century (Morton, 1846) Causes nausea and is highly flammable 1960s developed nonflammable anesthetics Cl F F Cl F HH-C-C-O-C-H F F F H F H Ethane(enflurane) Penthrane

137. MTBE Methyl tert-butyl ether CH 3 CH 3 -O-C-CH 3 CH 3 Second in production or organic chemicals Additive to improve gasoline performance

138. Carboxylic acids These compounds end with a COOH group where the C has a double bonded O and a single bonded OH The ending of the parent chain changes from “ane” etc. to “oic” and add the word acid Ex: CH 3 CH 2 CH 2 COOH Butanoic acid

139. Carboxyl Group Carboxylic acids contain the carboxyl group on carbon 1. O  CH 3 — C—OH= CH 3 —COOH carboxyl group

140. Naming Carboxylic Acids Formula IUPAC Common alkan -oic acid prefix – ic acid HCOOH methanoic acid formic acid CH 3 COOH ethanoic acid acetic acid CH 3 CH 2 COOH propanoic acid propionic acid CH 3 CH 2 CH 2 COOH butanoic acid butyric acid

141. Naming Rules Identify longest chain (IUPAC) Number carboxyl carbon as 1 CH 3 | CH 3 — CH—CH 2 —COOH IUPAC 3-methylbutanoic acid

142. Learning Check CA1 Give IUPAC and common names: A. CH 3 COOH CH 3 | B. CH 3 CHCOOH

143. Solution CA 1 A. CH 3 COOH ethanoic acid; acetic acid CH 3 | B. CH 3 CHCOOH 2-methylpropanoic acid;

144. Properties Carboxylic acids are weak acids CH 3 COOH + H 2 O CH 3 COO – + H 3 O + Neutralized by a base CH 3 COOH + NaOH CH 3 COO – Na + + H 2 O

145. Phenols IUPAC name for benzene with a hydroxyl group Many are used as antiseptics and disinfectants

146. Phenols in Medicine

147. Compounds with Oxygen Atoms Alcohols-OH hydroxyl CH 3 -OH CH 3 CH 2 -OH Phenols Ethers -O- CH 3 -O-CH 3

148. Learning Check Al1 Classify each as an alcohol (1), phenol (2), or an ether (3): A. _____ CH 3 CH 2 -O-CH 3 C. _____ CH 3 CH 2 OH B. _____

149. Solution Al 1 Classify each as an alcohol (1), phenol (2), or an ether (3): A. __3__ CH 3 CH 2 -O-CH 3 C. __1__ CH 3 CH 2 OH B. _ 2__

150. Thiols Contain the functional group -SH Named by adding thiol to the name of the longest carbon chain Number the -SH group in longer chains CH 3 -SH methanethiol CH 3 -CH 2 SH ethanethiol SH CH 3 -CH-CH 3 2-propanethiol

151. Thiols Many thiols have disagreeable odors Used to detect gas leak Found in onions, oysters, garlic and oysters Onions CH 3 CH 2 CH 2 -SH 1-propanethiol Garlic CH 2 = CHCH 2 -SH 2-propene-1-thiol Skunk spray CH 3 trans-2-butene-1-thiol CH = CH CH 2 SH

152. Amines Organic compounds of nitrogen N Classified as primary, secondary, tertiary CH 3 CH 3  CH 3 —NH 2 CH 3 —NH CH 3 —N — CH 3 1° 2° 3°

153. Naming Amines IUPAC aminoalkane Common alkylamine CH 3 CH 2 NH 2 CH 3 —NH —CH 3 aminoethane N-methylaminomethane (ethylamine) (dimethylamine) NH 2 | CH 3 CHCH 3 2-aminopropane AnilineN-methylaniline (isopropylamine)

154. Learning Check AM1 Give the common name and classify: A. CH 3 NHCH 2 CH 3 CH 3 | B.CH 3 CH 2 NCH 3

155. Solution AM1 A.CH 3 NHCH 2 CH 3 ethylmethylamine, 2° CH 3 | B.CH 3 CH 2 NCH 3 ethyldimethylamine, 3°

156. Alkaloids Physiologically active nitrogen-containing compounds Obtained from plants Used as anesthetics, antidepressants, and stimulants Many are addictive

157. Nicotine

158. Caffeine

159. Procaine

160. Leaning Check AM2 Write a structural formula for A. 1-aminopentane B. 1,3-diaminocyclohexane

161. Solution AM2 A. 1-aminopentane CH 3 CH 2 CH 2 CH 2 CH 2 -NH 2 B. 1,3-diaminocyclohexane

162. Amides Derivatives of carboxylic acids where an amino (-NH 2 ) group replaces the –OH group. O O   CH 3 — C—OH CH 3 — C—NH 2 carboxylic acid amide ethanoic acidethanamide

163. Naming Amides Alkanamidefrom acid name O  methanamide (IUPAC) HC–NH 2 formamide (common) O  propanamide (IUPAC) CH 3 CH 2 C–NH 2 propionamide(common)

164. Naming Amides with N-Groups O  CH 3 C–NHCH 3 N-methylethanamide (IUPAC) N-methylacetamide (common) O  CH 3 CH 2 C–N(CH 3 ) 2 N,N-dimethylpropanamide N,N-dimethylpropionamide

165. Aromatic Amides

166. Learning Check AM3 Name the following amides: O  A. CH 3 CH 2 CH 2 C–NH 2 O  B. CH 3 C–N(CH 2 CH 3 ) 2

167. Solution AM3 O  A. CH 3 CH 2 CH 2 C–NH 2 butanamide; butryamide (common) O  B.CH 3 C–N(CH 2 CH 3 ) 2 N,N-diethylethanamide; N,N-diethylacetamide

168. Learning Check AM4 Draw the structures of A.Pentanamide B.N-methylbutyramide

169. Solution AM4 A.Pentanamide O  CH 3 CH 2 CH 2 CH 2 C–NH 2 B.N-methylbutyramide O  CH 3 CH 2 CH 2 C–NHCH 3

170. Esters In and ester, the H in the carboxyl group is replaced with an alkyl group O  CH 3 — C—O —CH 3 = CH 3 —COO —CH 3 ester group

171. Esters in Plants Esters give flowers and fruits their pleasant fragances and flavors.

172. Naming Esters Name the alkyl from the alcohol –O- Name the acid with the C=O with –ate acidalcohol O  methyl CH 3 — C—O —CH 3 Ethanoate methyl ethanoate (IUPAC) (acetate)methyl acetate (common)

173. Some Esters and Their Names Flavor/Odor Raspberries HCOOCH 2 CH 3 ethyl methanoate (IUPAC) ethyl formate (common) Pineapples CH 3 CH 2 CH 2 COOCH 2 CH 3 ethyl butanoate (IUPAC) ethyl butyrate (common)

174. Learning Check CA 2 Give the IUPAC and common names of the following compound, which is responsible for the flavor and odor of pears. O  CH 3 — C—O —CH 2 CH 2 CH 3

175. Solution CA2 O  propyl CH 3 — C—O —CH 2 CH 2 CH 3 proply ethananoate (IUPAC) propyl acetate (common)

176. Learning Check CA 3 Draw the structure of the following compounds: A.3-bromobutanoic acid B.Ethyl propionoate

177. conformations 3 dimensional molecular structures interrelated by rotations about the bonds. Ex. Ethane C 2 H 6 Can be described as eclipsed and staggered. See handout

178. Hydrogenation Adds a hydrogen atom to each carbon atom of a double bond H H H H Ni H–C=C–H + H 2 H–C–C–H H H ethene ethane

179. Products of Hydrogenation Adding H 2 to vegetable oils produces compounds with higher melting points Margarines Soft margarines Shortenings (solid)

180. Learning Check HA4 What is the product of adding H 2 (Ni catalyst) to 1-butene?

181. Solution HA4 What is the product of adding H 2 (Ni catalyst) to 1-butene? Ni CH 2 =CHCH 2 CH 3 + H 2 CH 3 CH 2 CH 2 CH 3

182. Adding Halogens Halogens also add to the double bond of an alkene. H 2 C  CH 2 + Cl 2

183. Learning Check HA5 Write the product of the following addition reactions: CH 3 CH=CHCH 3 + H 2

184. Solution HA5 Write the product of the following addition reactions: CH 3 CH=CHCH 3 + H 2 CH 3 CH 2 CH 2 CH 3

185. Unsaturated Fatty Acids Fatty acids in vegetable oils are omega-6 acids (the first double bond occurs at carbon 6 counting from the methyl group) A common omega-6 acid is linoleic acid CH 3 CH 2 CH 2 CH 2 CH 2 CH=CHCH 2 CH=CH(CH 2 ) 7 COOH 6 linoleic acid, a fatty acid

186. Trans Fats  In vegetable oils, the unsaturated fats usually contain cis double bonds.  During hydrogenation, some cis double bonds are converted to trans double bonds (more stable) causing a change in the fatty acid structure  If a label states “partially” or “fully hydrogenated”, the fats contain trans fatty acids.

187. Trans Fats  In the US, it is estimated that 2-4% of our total Calories is in the form of trans fatty acid.  trans fatty acids behave like saturated fatty acids in the body.  Several studies reported that trans fatty acids raise LDL-cholesterol. Some studies also report that trans fatty acid lower HDL-cholesterol  The trans fatty acids controversy will continue to be debated.

188. Fats and Atheroschlerosis Inuit people of Alaska have a high fat diet and high blood cholesterol levels, but a very low occurrence of atherosclerosis and heart attacks. Fat in the Intuit diet was primarily from fish such as salmon, tuna and herring rather than from land animals (as in the American diet).

189. Omega-3 Fatty Acids Fatty acids in the fish oils are mostly the omega-3 type (first double bond occurs at the third carbon counting from the methyl group). linolenic acid 18 carbon atoms CH 3 CH 2 CH=CHCH 2 CH=CHCH 2 CH=CH(CH 2 ) 7 COOH  eicosapentaenoic acid (EPA) 20 carbon atoms CH 3 CH 2 (CH=CHCH 2 ) 5 (CH 2 ) 2 COOH

190. Learning Check HA6 (1) Ture or (2) False A. ____ There are more unsaturated fats in vegetable oils. B. ____ Vegetable oils have more omega-3 oils than found in fish. C. ____ Hydrogenation of oils converts some cis-double bonds to trans- double bonds. D. ____ Animal fats have more saturated fats.