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Organic Nomenclature

Organic Nomenclature. IUPAC. International Union of Pure and Applied Chemistry Systematic way to name compounds Attempts to name compounds In a logical and simple fashion To give each compound one unique name (One compound, one name). Parts of a Compound. Functional Groups’ Priority.

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Organic Nomenclature

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  1. Organic Nomenclature

  2. IUPAC • International Union of Pure and Applied Chemistry • Systematic way to name compounds • Attempts to name compounds • In a logical and simple fashion • To give each compound one unique name (One compound, one name)

  3. Parts of a Compound

  4. Functional Groups’ Priority I. Carbonyl Groups C=O (Highest) • Carboxylic Acid R-COOH • Esters R-COOR • Amides R-CONH2, (NHR, NR2) • Aldehydes R-CHO • Ketones R-COR

  5. Functional Groups’ Priority II. Non-Carbonyl Groups • Alcohol ROH • Amine RNH2, (NHR, NR2)

  6. Functional Groups’ Priority III. Parent Group (Root) • Alkyne -C=C- (Name) • Alkene -CH=CH- (Numbering) • Alkane RH

  7. Functional Groups’ Priority IV. Substitutive Groups • Side Chains R-r • Ethers ROR • Halogens RF (Br, Cl, I) • Lower Order Functional Groups

  8. Rules • Find the longest continuous chain with the highest order functional group. • Number the chain • starting at the end and giving the highest order functional group the lowest number possible • If no high order functional groups, then number the longest chain giving the side chains the lowest number possible at the first point of difference • If two or more chains are equally the longest, select the chain with the greatest number of side chains

  9. Rules • Name the Prefix of the parent based on the number of carbons Meth, Eth, Prop, But, Pent, Hex, Hept, Oct, Non, Dec • Add the Root of the parent alkane (an), alkene (en), alkyne (yn) • If the root is an alkene or alkyne, place a number (Locant) indicating the location of the double or triple bond in front of the prefix of the parent chain.

  10. Rules • Add the suffix (ending) to the parent to indicate the highest order functional group. • Place the locant for the functional group in front of the parent for alkanes and in between root and suffix for alkenes and alkynes • Add side chain prefixes and substitutive group prefixes with locant to front in alphabetical order.

  11. Functional Group Prefix & Suffixes • Carboxylic Acid carboxy- -oic acid • Esters -oate • Amides -amide • Aldehydes oxo- -al • Ketones oxo- -one • Alcohol hydroxy- -ol • Amine amino- -amine

  12. Substitutive Group Indicators • Side Chains alkyl- (yl) • Ethers alkoxy- (oxy) • Halogens • fluoro • Chloro • Bromo • Iodo • Nitrated compounds –NO2 nitro- • Ring Structures cyclo-

  13. Root Suffixes • Alkyne -yne • Alkene -ene • Alkane -ane Multiples Prefixes • di • tri • tetra • penta • hexa • hepta • octa • nona • deca

  14. Special Case Side Chains

  15. Special Case Side Chains

  16. Special Case Side Chains

  17. Special Case Side Chains

  18. Bicyclo compounds

  19. Bicyclo compounds

  20. Bicyclo compounds • Start numbering at a bridge head • Number the longest bridge first then next longest and then shortest • Count carbons in each bridge (Do not count bridge heads • Starting with longest to shortest place bridge counts in brackets after bicyclo prefix (i.e. bicyclo [3.2.1] octane)

  21. Problems (P.188) • 4.23 • 4.24 • 4.26 • 4.29 • 4.48

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