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CHAPTER 11 BONDING AND MOLECULAR STRUCTURE:

CHAPTER 11 BONDING AND MOLECULAR STRUCTURE:. ORGANIC CHEMISTRY All bold numbered problems. Overview. Organic chemistry is the study of compounds containing carbon combined with other non-metals. Bonding plays a critical role in understanding the reactivity of these compounds.

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CHAPTER 11 BONDING AND MOLECULAR STRUCTURE:

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  1. CHAPTER 11BONDING AND MOLECULAR STRUCTURE: ORGANIC CHEMISTRY All bold numbered problems.

  2. Overview • Organic chemistry is the study of compounds containing carbon combined with other non-metals. • Bonding plays a critical role in understanding the reactivity of these compounds. • These compounds are referred to as hydrocarbons since they are primarily hydrogen and carbon.

  3. Overview

  4. Overview • Carbon uses sp3, sp2, and sp hybridization in forming the four bonds per carbon atom common to almost all carbon compounds. • With sp hybridization, there are two (2) p bonds and 1 s bonds. • With sp2 hybridization there is one (1) p bond and 1 s bonds.

  5. Why Carbon sp3, sp2, and sp hybridization

  6. Allotropes of Carbon Carbon only (no other atom) compounds

  7. FUNCTIONAL GROUPS Organic chemistry is the study of compounds containing carbon.The goal of studying Organic chemistry is the making of carbon-carbon bonds, C-X, C-O, C-N, and C-S bonds to make new molecules • Alkane • Alkene • Alkyne • Alkyl halide • Aromatic • Alcohol • Ethers • Aldehyde • Ketone • Carboxylic Acid • Ester • Amine • Amide importance Inorganic molecules like CO, and CO3-2 are not considered organic molecules.

  8. 1. Alkanes

  9. Figure 11.4 10

  10. Alkanes 12

  11. Abbreviated, common method to write organic cmpds

  12. ALKANES • There are frequently many hydrocarbons with the same formula. These are called structural isomers. C5H12 has three isomers C10H22 has 75 isomers C20H42 has 366,319 isomers

  13. Isomers of Butane-5 Carbon chains

  14. C6H14 has five isomers, draw them.

  15. Cycloalkanes • Cycloalkanes are ring structures and have the general formula CnH2n. • Do not confuse these compounds with the alkenes which have the same general formula.

  16. 2. ALKENE AND 3. ALKYNE • These compounds are referred to as unsaturated. • Alkenes contain one or more double bonds and alkynes contain one or more triple bonds.

  17. Saturated –vs- Unsaturated Saturated Hydrocarbon C15H32

  18. Unsaturated Hydrocarbon Contains either double and/or triple bonds Notice how the chains do not line up

  19. Single bonds only Fats Double bonds Fats

  20. ALKENES

  21. ALKYNE

  22. Physical properties change Isomers have different physical as well as different chemical properties

  23. Nomenclature • Organic Functional Groups and Nomenclature • Substituents - saturated carbon substituents are called alkyl groups and are named based on the naming of the normal alkanes. H t h l m e y C H C H 3 M e H H H C H H e h C t y l C C H E t 2 3 H H

  24. NomenclatureHaloalkane

  25. Alcohol

  26. Ether

  27. Amine

  28. Aldehyde

  29. Ketone

  30. Carboxylic acid

  31. Ester

  32. Amide

  33. Draw the following • Dibutyl ether • Butanoic acid • Ethyl butanoate • Butyl amine • Dibutyl amine • Tributyl amine • Butane • Butene • Butyne • Butanol • Butanal • Butanone

  34. Common Alcohol Names

  35. What is the name of this Alcohol? alcohol methyl Methanol

  36. The main chain is numbered such that the first substituent encountered along the chain receives the lowest possible number. C H 3 C C C C C 1 2 3 4 5 2 - m e t h y l p e n t a n e NOT C H 3 C C C C C 5 4 3 2 1 4 m t t - e h y l p e n a n e

  37. C H C H 3 3 C C C C C 1 2 3 4 5 , - i t p a 2 4 d m e h y l e n t n e If two or more identical substituents are attached to the same C-chain , prefixes di-, tri-, tetra-, etc. are used with numbers to indicate position. C H 3 2 C C C C C 5 1 4 3 C H 3 2 , - d i m e t h y l p e n t a n e 2

  38. If two different substituent's are attached to the carbon chain, name them in alphabetical order. C H C H C H 2 3 3 C C C C C C C 1 2 3 4 5 6 7 3-ethyl, 5-methylheptane Numbering starts at the side with the heavier functional Group Numbering starts closest to 1st functional group

  39. C C C C C C C C C C C C C C 3 6 4 5 C C 2 1 Practice 3-ethylhexane

  40. Nomenclature of Branched Alkyl Chains Two alkyl groups can be derived from propane

  41. Nomenclature of Branched Alkyl Chains Four groups can be derived from the butane isomers

  42. Examples

  43. Classification of Hydrogen Atoms Hydrogens take their classification from the carbon they are attached to

  44. Nomenclature of Alkyl Halides In common nomenclature the simple haloalkanes are named as alkyl halides Common nomenclature of simple alkyl halides is accepted by IUPAC and still used

  45. B r C l C C C C C B r B r C C C C C B r Practice 2-bromo-4-chloropentane 2,2,4-tribromopentane

  46. IUPAC Substitutive Nomenclature An IUPAC name may have up to 4 features: locants, prefixes, parent compound and suffixes Numbering generally starts from the end of the chain which is closest to the group named in the suffix IUPAC Nomenclature of Alcohols Select the longest chain containing the hydroxyl and change the suffix name of the corresponding parent alkane from -ane to -ol Number the parent to give the hydroxyl the lowest possible number The other substituents take their locations accordingly

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