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Organic Chemistry: The Infinite Variety of Carbon Compounds

Organic Chemistry: The Infinite Variety of Carbon Compounds. Overview : Introduction to Organic chemistry with an emphasis on CARBON Hydrocarbons Functional groups Unsaturation Oxygen containing Nitrogen containing. Organic Chemistry.

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Organic Chemistry: The Infinite Variety of Carbon Compounds

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  1. Organic Chemistry: The Infinite Variety of Carbon Compounds

  2. Overview: • Introduction to Organic chemistry with an emphasis on CARBON • Hydrocarbons • Functional groups • Unsaturation • Oxygen containing • Nitrogen containing

  3. Organic Chemistry Organic chemistry is defined as the chemistry of carbon compounds. Of tens of millions of known chemical compounds, over 95% are compounds of carbon.

  4. The Unique Carbon Atom Carbon has 4 valence electrons and can make 4 bonds in a tetrahedralarrangement

  5. The Unique Carbon Atom Carbon is unique in that carbon atoms can bond to each other to form long chains and rings.

  6. The Unique Carbon Atom Carbon can from bonds to elements other than hydrogen. This chapter also covers compounds where carbon is bonded to: carbon-oxygen: carbon-nitrogen: & carbonhalogen

  7. The Unique Carbon Atom In important feature when studying organic compounds is polarity. The more C-H bonds the less polar. The more C-O, C-N, C-Cl bonds the more polar the compound. Consulting the electronegativity (EN) table: Bond DEN polarity C –H2.5-2.1= 0.4 nonpolar O-C3.5-2.5= 1.0 POLAR N-C3.0-2.5= 0.5 POLAR Cl-C3.0-2.5= 0.5 POLAR

  8. Hydrocarbons Hydrocarbons are the simplest organic compounds. As their name implies, they are composed entirely of hydrogenand carbon. • Alkanes • Cyclic hydrocarbons • Alkenes • Alkynes • Aromatics • Chlorinated hydrocarbon

  9. Alkanes Alkanesare hydrocarbons that contain only single bonds. Because all carbon-to-carbon bonds are single bonds, alkanesare often called saturated hydrocarbons. The simplest hydrocarbon is methane (CH4). Alkaneshave the general formula CnH2n+2

  10. Alkanes The names of alkanes begin with a prefix (STEM) denoting the number of carbon atoms followed by the suffix –ane.

  11. Alkanes Isomerism:Isomersare compounds with the same molecular formula, but different structural formulas. C4H10 C4H10 CnH2n+2

  12. Cyclic Hydrocarbons Cyclic hydrocarbons are ring compounds. The simplest cyclic hydrocarbon is cyclopropane. CnH2n

  13. Alkyl Groups When an alkaneis added as a branch to another organic compound it is referred to as an Alkyl group The simplest attachment of an Alkyl groups is at a terminal carbon. Theyaregiven a name like the stemof an alkane with a ‘yl’ ending tack on. prop yl yl but

  14. Alkyl Groups If the carbonof attachment is connected to two carbons “sec” (secondary) is used. If it is connected to three carbons “tert” (tertiary) is used “ iso” implies symmetryabout the attachment

  15. Unsaturated Hydrocarbons Alkenesare hydrocarbons that contain a carbon-to-carbondouble bond. Their general formulas are CnH2n Their names begin with a prefix (STEM) denoting the number of carbon atoms followed by the suffix –ene. Ethylene is the simplest alkene.

  16. Unsaturated Hydrocarbons Alkynesare hydrocarbons that contain a carbon-to-carbontriple bond. Their general formulas are CnH2n-2 Their names begin with a prefix (STEM) denoting the number of carbon atoms followed by the suffix –yne. Ethyne (acetylene) is the simplest alkyne

  17. Aromatic Hydrocarbons: Benzene and Relatives Benzeneis a unique organiccompound in that it is a very stable six-sided ring. Aromatic hydrocarbons contain a benzenering or have properties similar to those of Benzene.

  18. Chlorinated Hydrocarbons When hydrogen atoms of a hydrocarbon are substituted by chlorine, a chlorinatedhydrocarbon is formed. Chlorinatedhydrocarbons have many useful properties. Dichloromethane is used as a solvent and paint remover. Trichloromethane(chloroform) is also a solvent and at one time was used as an anesthetic. It is now considered hazardous.

  19. Hydrocarbons: Review • Alkanes • Cyclic hydrocarbons • Alkenes • Alkynes • Aromatics • Chlorinated hydrocarbon CnH2n+2

  20. Hydrocarbons: Review • Alkanes • Cyclic hydrocarbons • Alkenes • Alkynes • Aromatics • Chlorinated hydrocarbon

  21. Hydrocarbons: Review • Alkanes • Cyclic hydrocarbons • Alkenes • Alkynes • Aromatics • Chlorinated hydrocarbon CnH2n

  22. Hydrocarbons: Review • Alkanes • Cyclic hydrocarbons • Alkenes • Alkynes • Aromatics • Chlorinated hydrocarbon CnH2n-2

  23. Hydrocarbons: Review • Alkanes • Cyclic hydrocarbons • Alkenes • Alkynes • Aromatics • Chlorinated hydrocarbon

  24. Hydrocarbons: Review • Alkanes • Cyclic hydrocarbons • Alkenes • Alkynes • Aromatics • Chlorinated hydrocarbon

  25. Functional Groups Atoms or groups of atoms attached to hydrocarbon skeletons give the compounds characteristic chemical and physical properties and are known as functional groups. Double and triple bonds, as well as halogensubstituents, are examples of functional groups.

  26. Functional Groups: Hydrocarbons R = organic

  27. Functional Groups: Oxygen

  28. Functional Groups: Oxygen Some alcoholscontain more than one hydroxyl group. Carbon makes one bond to oneOxygen Alcoholscontain the hydroxyl (-OH) functional group.

  29. Phenols Phenolsare aromatic compounds with the hydroxyl group attached to the aromatic ring. The presence of the aromatic ring alters the properties of the hydroxyl group. Phenolsdo not act as alcohols, but as acids. Phenolsare an effective antiseptic.

  30. Functional Groups: Oxygen Two different Carbons makes one bond to same oneOxygen Ethyl methyl ether General formula: ROR or ROR’ Naming: name the larger alkyl group then the smaller: add the term etherat the end

  31. Functional Groups: Oxygen = TERMINALCarbon makes TWO bonds to one Oxygen = = Compounds contain the carbonyl (C=O) functional group. O General formula: R-C-H Naming: ends in ‘aldehyde’: (formaldehyde) =

  32. Functional Groups: Oxygen INTERIORCarbon makes TWO bonds to oneOxygen Compounds contain the carbonyl (C=O) functional group. methyl methyl ketone ‘acetone’ O General formula: R-C-R` Naming: name the larger alkyl group then the smaller: add the term ketone or ‘one’ at the end =

  33. Functional Groups: Oxygen Carbon makes TWO bonds to oneOxygen AND one bond to anotherOxygen (which has an acidic Hydrogen) Compounds contain the carbonyl (C=O) functional group and the hydroxyl (-OH) functional group Amino acid O General formula: R-C-OH or RCOOH Naming: Take alkane name, drop ‘e’ and add ‘oic acid’ =

  34. Functional Groups: Oxygen Carbon makes TWO bonds to oneOxygen AND one bond to anotherOxygen (which binds another Carbon) Compounds contain the carbonyl (C=O) functional group and an INTERIOROxygen O General formula: R-C-OR` Naming: Name alcohol first then the acid; ends in ‘ate’ =

  35. Functional Groups: Nitrogen

  36. Functional Groups: Nitrogen Amino acid Carbon makes single bond to oneNitrogen: More than one carbon can be singly bond to the Nitrogen Aminesare derivatives of ammonia (NH3) and have similar odors. Aminenames end in ‘ine’ “Trimethyamine” fishy odor

  37. Functional Groups: Nitrogen Carbonyl carbon makes single bond to one Nitrogen: More than one carbon can be singly bond to the Nitrogen Naming: Take alkane name, drop ‘e’ and add ‘amide’ 1 2 + + H2O

  38. Summary: Organic molecules contain CARBON Hydrocarbons contain hydrogens and carbons (some have Chlorine) and can contain double and triple bonds (alkenes and alkynes) Carbon-Oxygen Functional groups progress for a single bond to an oxygen(alcohols) to double bonded (carbonyls) to double and single bounded (carboxylic acids, esters) Carbon-Nitrogen Function groups progress from a single bond to a nitrogen(amine) to a carbonyl carbon bound to a nitrogen (amide)

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