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Functional Groups Functional groups: special groups of atoms attached to a hydrocarbon skeleton; the most common sites of chemical reactivity.

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Presentation on theme: "Functional Groups Functional groups: special groups of atoms attached to a hydrocarbon skeleton; the most common sites of chemical reactivity."— Presentation transcript:

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2 Functional Groups Functional groups: special groups of atoms attached to a hydrocarbon skeleton; the most common sites of chemical reactivity.

3 Organic halides: a hydrogen is replaced by a halogen fluoro-, chloro-, bromo-, iodo- 2-iodobutane

4 Organic halides: a hydrogen is replaced by a halogen fluoro-, chloro-, bromo-, iodo- 2,4-dibromo-1-hexene

5 Organic halides: a hydrogen is replaced by a halogen fluoro-, chloro-, bromo-, iodo- 1-bromo-2-chlorobenzene

6 Alcohols & phenols: contain the hydroxyl group (-OH) alcohols: at least 1 H on a hydrocarbon is replaced by OH phenols: at least 1 H on an aromatic ring is replaced by OH 2-propanol

7 Alcohols & phenols: contain the hydroxyl group (-OH) alcohols: at least 1 H on a hydrocarbon is replaced by OH phenols: at least 1 H on an aromatic ring is replaced by OH 3-methyl-1-butanol

8 Alcohols & phenols: contain the hydroxyl group (-OH) alcohols: at least 1 H on a hydrocarbon is replaced by OH phenols: at least 1 H on an aromatic ring is replaced by OH 1,2-butanediol

9 ethers: compounds in which an O atom is bonded to 2 organic groups: -C-O-C- methoxymethane (dimethyl ether)

10 ethers: compounds in which an O atom is bonded to 2 organic groups: -C-O-C- methoxypropane (methyl propyl ether)

11 ethers: compounds in which an O atom is bonded to 2 organic groups: -C-O-C- methoxybenzene (methyl phenyl ether)

12 Carboxylic acids: compounds that contain the carboxyl group (general formula is R-COOH) butanoic acid

13 Carboxylic acids: compounds that contain the carboxyl group (general formula is R-COOH) ethanoic acid

14 Carboxylic acids: compounds that contain the carboxyl group (general formula is R-COOH) 3-methylpentanoic acid

15 Carboxylic acids: compounds that contain the carboxyl group (general formula is R-COOH) benzoic acid

16 amines: derivatives of ammonia (NH 3 ) in which 1 or more H atoms are replaced by organic groups (alkyl or aryl groups) ammonia

17 amines: derivatives of ammonia (NH 3 ) in which 1 or more H atoms are replaced by organic groups (alkyl or aryl groups) methylamine

18 amines: derivatives of ammonia (NH 3 ) in which 1 or more H atoms are replaced by organic groups (alkyl or aryl groups) trimethylamine

19 amines: derivatives of ammonia (NH 3 ) in which 1 or more H atoms are replaced by organic groups (alkyl or aryl groups) 2-aminobutane

20 amines: derivatives of ammonia (NH 3 ) in which 1 or more H atoms are replaced by organic groups (alkyl or aryl groups) 1-amino-3-propylcyclohexane

21 *aniline: the simplest aromatic amine aniline

22 *aniline: the simplest aromatic amine 3,5-dichloroaniline Naming it aniline make this carbon #1 by definition

23 *aniline: the simplest aromatic amine N,N-dimethylaniline

24 Summary of IUPAC rules for naming organic compounds IUPAC: International Union of Pure and Applied Chemistry International, non-governmental organization that is best known for its system of nomenclature, which is now recognized as the world authority in this field.

25 Rule #1: Identify the longest chain of carbon atoms a) The longest chain of carbon atoms gives the stem/root of the name as shown in the table below: # of C-atoms in longest chain Stem in IUPAC name Example (C 2 H 2n+2 for alkanes) 1meth- CH 4, methane 2eth- C 2 H 6, ethane 3prop- C 3 H 8, propane 4but- C 4 H 10, butane 5pent- C 5 H 12, pentane 6hex- C 6 H 14, hexane 7hept- C 7 H 16, heptane 8oct- C 8 H 18, octane 9non- C 9 H 20, nonane

26 b) If two chains have equal lengths, pick the one with more branch points. Rule #1: Identify the longest chain of carbon atoms

27 Rule #2: Number the carbons in the main chain Number chain to minimize the position/number of the following in order of priority: a) thing youre naming the compound after (double bond if alkene; -OH group if alcohol, etc) a) note: for multiple double bonds -diene, -triene, -tetraene b) first branch/substituent group c) If both ends have the same first branching number, then number chain to minimize position of second branch (and then third and so on). d) if still in need of a tie breaker, minimize # of substituent group that comes first alphabetically Note: in cyclic and aromatic (benzene derivatives) compounds, no number needed if only one substituent.

28 Rule #3: Identify the functional group and attach appropriate suffix Note: the name for the stem/root is derived from the longest carbon chain, which may include the carbon of the functional group. Indicating position of the functional group: shown by a number inserted before the functional group ending. The number refers to the carbon atom to which the functional group is attached when the chain is numbered starting at the end that will give the smallest number to the group.

29 Class of compound Functional group Suffix in IUPAC name alkane -ane alkene -ene alkyne -yne alcohol -anol aldehyde -anal ketone -anone carboxylic acid -anoic acid amine -anamine

30 Rule #4: Identify the side chains or substituent groups Assign number of carbon at point of attachment. Side chain/ substituent groupPrefix in IUPAC nameExample -CH 3 methyl-2-methylpropane -C 2 H 5 ethyl3-ethylpentane -C 3 H 7 propyl-4-propylheptane -F, -Cl, -Br, -I fluoro-, chloro-, bromo-, iodo-tetrachloromethane -NH 2 amino-2-aminoethanioic acid

31 Rule #5: Assemble name as a single word #, substituent, root, suffix a) List substituents alphabetically (i.e. butyl- before methyl-) b) If multiples of one substituent are present: di-, tri-, tetra, etc. Note: di-, tri-, tetra, etc. arent part of alphabetical name (triethyl- before dimethyl-) c) punctuation: commas between numbers; hyphens between numbers and letters; merged into one word (exception: acid = word #2 for carboxylic acids)


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