1 Organic Chemistry: the study of carbon containing compounds. Prior to 1828, organic compounds can only be obtained from living organism until Fredrick Wohler prepared urea - chemical in urine (an organic compound) NH 4 Cl + AgNCO → NH 2 -CO-NH 2 + Ag Now - the bulk of organic compounds are manufactured in the lab. Clothes perfumes shoes athletic products foods Makeup furniture computers televisions cars Plastics CD dishes cups carpets linoleum etc

2 EXCEPTIONS Inorganic compounds: containing carbon atoms Oxides / like CO and CO 2 are inorganic examples Cyanides / like NaCN Mg(CN) 2 are inorganic compounds Carbonates /like Na 2 CO 3 MgCO 3 are inorganic compounds Carbides / like SiC Al 4 C 3 are inorganic compounds

3 BOND CAPACITY OF ATOMS H C O N F Cl Br I C O N F ClBr H HYDROCARBONS GROUPS OF ORGANIC COMPOUNDS CONTAINING HYDROGEN AND CARBON ALIPHATICSAROMATICS Alkanes Alkenes Alkynes Cyclic compounds Have distinct cyclic carbon ring Are not named for their Aroma

4 HYDROCARBONS ALIPHATICS ALKANES ALKENES ALKYNES SINGLE BONDS DOUBLE BONDS TRIPLE BONDS C N H 2N+2 C N H 2N C N H 2N-2 N – REPRESENTS C ATOMS AROMATICS CONTAIN BENZENE RING CYCLIC COMPOUNDS COLORLESS,FLAMMABLE LIQUID SWEET AROMA CARCINOGENIC EFFECT AROMATICS MEAN THAT - CONJUGATED RINGS OF CARBON - UNSATURATED BONDS OF C - RESONANT BONDS OF CARBON

I. Classes of Organic Compounds Hydrocarbons (C & H only)Heteroatomic compounds AliphaticAromatic * Alkanes * Alkenes * Alkynes * Cyclic compounds * Alcohols * ethers aldehydes ketones Carboxylic acids * Esters * amines amides benzene ring

6 What is the general formula of alkanes?(C n H 2n + 2 )

7 BRANCHES - OFF PARENT CHAIN ALL WILL APPEAR TO HAVE C AND H THE BRANCHES WILL HAVE ONE LESS HYDROGEN AND ARE CALLED ALKYLS METH - 1 ETH - 2 PROP - 3 BUT - 4 PENT - 5 HEX - 6 HEPT - 7 OCT - 8 NON - 9 DEC - 10 METHYL - CH 3 ETHYL - C 2 H 5 PROPYL - C 3 H 7 BUTYL - C 4 H 9 PENTYL - C 5 H 11 HEXYL - C 6 H 13 HEPTYL - C 7 H 15 AND SO ON !! CH 3 CH 3 -CH 2 CH 3 -CH 2 -CH 2 CH 3 -CH 2 -CH 2 -CH 2 CH 3 -CH 2 -CH 2 -CH 2 -CH 2 CH 3 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 CH 3 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 AND SO ON !!!! PREFIX - C ALKYL FORMULACONDENSED STRUCTURAL

8 H H C CH 3 methyl H H H H C CCH3-CH2 ethyl H H Branches off parent chainNot part of the parent chain in a sequence

9 Ways of presenting organic compounds Structure formula - shows connectivity of atoms in a compound Molecular formula - indicate type and number of atoms C 3 H 8 Condensed structural formula - shows connecting group of atoms in a compound CH 3 - CH 2 - CH 3 Line structural - shows hydrocarbons as lines with bends for carbon

10 CH 3 CH 3 -CH-CH 3 methyl groups CH 3 CH 3 CH 3 -CH-CH-CH 3 CH 2 CH 3 CH 3 -CH 2 -CH 2 -CH-CH 2 -CH 3 Ethyl group BRANCHES ARE NOT PART OF THE PARENT CHAIN !

11 1. Find the longest continuous chain of carbon atoms. Assign this chain as the parent name.(# of carbon atoms) 2. Determine the groups attached to the parent chain 3. Assign attachment position of group to main chain by starting at end which gives lowest position number. 4. Identical groups attached to the main chain are designated with prefixes. 2-di, 3-tri, 4-tetra, 5-penta 5. Different groups attached to main chain are written in alphabetical order.

12 CH 3 (branch) CH 3 -CH 2 -CH 2 -CH-CH 2 -CH 3 (parent chain) methylhexane on third C CH 3 six carbons (hex) NUMBER FROM RIGHT TO LEFT – BRANCH CLOSEST TO THE RIGHT SIDE !! CARBON NUMBER BRANCH PARENT CHAIN

13 NOMENCLATURE OF ALKANES 1. CARBON NUMBER OF BRANCH IS FIRST 2. THERE MAY BE SIMILAR BRANCHES – PLACE ALL CARBON NUMBERS IN ORDER. Eg 2,2,3 - 3,4,5 - separated by commas followed by a hyphen 3. THE NAME OF THE BRANCHES MUST FOLLOW – IF THERE ARE MULTIPLE BRANCHES YOU MUST ADD PRFIXES TO INDICATE HOW MANY … 2-DI 3 -TRI 4 -TETRA 5 - PENTA 6 - HEXA 4. THERE MAY BE DIFFERENT BRANCHES SO YOU MAY HAVE DIFFERENT ALKYL GROUPS AND CARBON NUMBERS… 3,3-diethyl-2,5,5-trimethyl (write down groups alphabetically – ignore prefix) 5. THE NAME OF THE PARENT CHAIN COMES LAST – ONE WORD 3,3- diethyl-2,5,5- trimethyloctane EASY !!

14 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 2,4-dimethylpentane 3,3,5-trimethylheptane

15 Write a condensed structure for A. 3,4-dimethylheptane B. 2,2-dimethyloctane

16 A. 3,4-dimethylheptane CH 3 CH 3 CH 2 CHCHCH 2 CH 2 CH 3 CH 3 2,2-dimethyloctane CH 3 CH 3 CCH 2 CH 2 CH 2 CH 2 CH 2 CH 3 CH 3 Solution Quiz

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

18 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

19 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

20 dichloromethane triodomethane tetrabromomethane dichlorodifluoromethane

21 bromomethane 2-chloropropane iodocyclohexane 2-bromo-2,4-dimethylpentane

22 Saturated compounds (alkanes) have the maximum number of hydrogen atoms attached to each carbon atom. Unsaturated compounds have fewer hydrogen atoms attached to the carbon chain than alkanes. Unsaturated compounds contain double or triple bonds

23 Alkene (C n H 2n ) 1. - ene suffix for alkenes 2. Main chain must include the double bond. 3. position of double bond indicated by prefix numbering location. 4. For multiple double bonds : di = 2 double bonds tri = 3 double bonds Alkyne (C n H 2n-2 ) 1. - yne suffix for alkynes 2. Nomenclature rules are similar to that of alkenes

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

25 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 2-pentyne 2-methyl-2-butene

26 same general formula as alkenes structural isomers of alkenes

27 Name the following: bromocyclopentane 1,3-dichlorocyclohexane

28 5-bromo-2-methylheptane 4-fluoro-1,2-dimethylcyclohexane 1,2,6-trichloro-4-ethyl-2-methylheptane

29 Same molecular formula Same number and types of atoms Different arrangement of atoms

30 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 used to form a branch, it makes a new isomer of C 4 H 10.

31 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 Write 3 isomers of C 5 H 12 and name each.

32 Draw all of the constitutional isomers for the following. C 4 H 9 Cl 1-chlorobutane2-chlorobutane1-chloro-2-methylpropane 2-chloro-2-methylpropane

unsaturated cyclic hydrocarbons

34 1. Monosubstituted a. group benzene chlorobenzeneethylbenzene b. special names: phenol 2. Benzene as a group - phenyl

35 A carbon compound that contain -OH (hydroxyl) group CH 4 methane CH 3 OH methanol CH 3 CH 3 ethane CH 3 CH 2 OH ethanol

36 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

37 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.

38 NameSuffixGroupExample Aliphaticane,ene,yneC - CC 4 H 10 Alcohol-olR - OHCH 3 -OH Ether-etherR - O - R´ CH 3 -O-CH 3 Aldehydes-alR – C = O H Ketones-one R - C - R´ O

39 NameSuffixGroupExample Carboxylic acid-oic acid R - C - OH O CH 3 COOH Ester-ateR - C - O - R´ O CH 3 COOCH 3 Amine Amide -amine -amide R - N - R´ R´ R - C - N – R´ O R´ CH 3 NH 2 CH 3 CONH 2

40 Contain an -O- between two carbon groups CH 3 -O-CH 3 dimethyl ether CH 3 -O-CH 2 CH 3 ethyl methyl ether

41 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. _____ Learning Check 3 2 1

42 Functional Groups CH 3 CH 2 CH 2 C O H aldehyde CH 3 CH 2 CCH 2 CH 3 O ketone

43 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 Aldehydes and Ketones

44 O  CH 3 -C-CH 3 CH 3 -C-CH 2 -CH 3 propanone 2-butanone Naming Ketones

45 Classify each as an aldehyde (1), ketone (2) or neither(3). O  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 Learning Check

46 Functional Groups carboxylic acid ester CH 3 CHCH 2 C O OH CH 3 CH 3 CH 2 C O OCH 2 CH 3

47 Functional groups alcoholalkene ester carboxylic acid ketone

48 carboxylic acid ether ester amine aldehyde

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