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Ch 22. Organic Compounds, Polymers,and Biochemicals

Ch 22. Organic Compounds, Polymers,and Biochemicals. Brady & Senese, 5th Ed. Index. 22.1. Organic chemistry is the study of carbon compounds 22.2. Hydrocarbons consist of only C and H atoms 22.3. Ethers and alcohols are organic derivatives of water

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Ch 22. Organic Compounds, Polymers,and Biochemicals

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  1. Ch 22. Organic Compounds, Polymers,and Biochemicals Brady & Senese, 5th Ed.

  2. Index 22.1. Organic chemistry is the study of carbon compounds 22.2. Hydrocarbons consist of only C and H atoms 22.3. Ethers and alcohols are organic derivatives of water 22.4. Amines are organic derivatives of ammonia 22.5. Organic compounds with carbonyl groups include aldehydes, ketones, and carboxylic acids 22.6. Polymers are composed of many repeating molecular units 22.7. Most biochemicals are organic compounds 22.8. Nucleic acids carry our genetic information

  3. Organic Compounds Are Diverse Carbon compounds are greatly variant due to the properties of C: • C is able to bond multiply • C is able to catenate • C is able to bond with a wide variety of elements • Isomers are possible when there is a carbon chain • Combinations of functional groups give great diversity • Carbon can form rings 22.1. Organic chemistry is the study of carbon compounds

  4. Carbon Compounds • Carbon containing compounds exist in large variety, mostly due to the multiple ways in which C can form bonds • Some groups of atoms with similar bonding are commonly seen, called functional groups. • Molecules may contain more than one functional group • Can form chiral compounds 22.1. Organic chemistry is the study of carbon compounds

  5. Show all atoms Show attachments between atoms but not how many pairs of electrons were used Show the geometric arrangement of the atoms VSEPR Structures 22.1. Organic chemistry is the study of carbon compounds

  6. show the general arrangement of the atoms and the number of atoms no effort is made to indicate geometry, types of bonds, or lone pairs Condensed Structures 22.1. Organic chemistry is the study of carbon compounds

  7. Alcohols & Ethers Are Polar • Contain C, H, and O, all with single bonds. • Alcohols end in –OH (R-OH) • Ethers have an O atom in the chain (R-O-R’) 22.1. Organic chemistry is the study of carbon compounds

  8. The Carbonyl Group • When C in a chain has a double bond to an oxygen, the group is termed a carbonyl • Aldehydes, ketones, carboxylic acids, and amides all contain carbonyl groups 22.1. Organic chemistry is the study of carbon compounds

  9. Aldehydes & Ketones Are Polar • Each has a carbon chain terminating in a carbonyl. • Aldehydes then have an added H (RCOH) • Ketones have another carbon chain (RCOR’) 22.1. Organic chemistry is the study of carbon compounds

  10. Amines & Amides Are Polar • Amines contain -NH2 on carbon chain (RNHR’) • Amides contain NH2 on carbon chain with carbonyl (RCONH2) 22.1. Organic chemistry is the study of carbon compounds

  11. Carboxylic Acids & Esters Are Polar • Both have a carbon chain terminating in a carbonyl • Carboxylic acids then have an –OH group • A combined carbonyl and hydroxyl group form a carboxyl group (RCOOH) • Esters then have a singly bound O, then another carbon chain (RCOOR’) 22.1. Organic chemistry is the study of carbon compounds

  12. Identify The Functional Groups Present 22.1. Organic chemistry is the study of carbon compounds

  13. Using Functional Groups • Collecting molecules into families means that only a few kinds of reactions must be learned • The emphasis is on the properties of the functional group, not individual molecules • Once the center of reactivity is identified, its characteristic reactions are expected to occur 22.1. Organic chemistry is the study of carbon compounds

  14. Functional Groups And Their Properties • Polar functional groups contain O and N • Like dissolves like: polar solvents will dissolve the polar functional groups • As the carbon chain increases in size, the polarity decreases 22.1. Organic chemistry is the study of carbon compounds

  15. Your Turn! Which of the following contains an amide group? • The top structure • The middle structure • The bottom structure • None of these 22.1. Organic chemistry is the study of carbon compounds

  16. Show all atoms, and all electrons Bond pairs usually shown as a line Non-bonding (lone) pairs of electrons are shown as dots Lewis Structures Of Hydrocarbons 22.2. Hydrocarbons consist of only C and H atoms

  17. Each vertex and terminus is a carbon Assumes that the termini contain as many H as needed for saturation of the C (hydrogens attached to hetero-atoms are shown) All hetero-atoms are shown explicitly Double bonds explicitly shown Stick Figures 22.2. Hydrocarbons consist of only C and H atoms

  18. Learning Check Fill in the missing atoms and derive the condensed structure C5H12 C4H8O2 22.2. Hydrocarbons consist of only C and H atoms

  19. Your Turn! Which is the correct formula for the structure shown? • C42H12 • C24H12 • C36G12 • None of these 22.2. Hydrocarbons consist of only C and H atoms

  20. Alkanes & Alkenes Are Non-polar • Alkanes are hydrocarbons (contain only C and H) • have a ratio of atoms CnH2n+2 • Alkenes- hydrocarbons with fewer H than the alkanes (CnH2n) • Use the same prefixes, but have the suffix -ene. 22.2. Hydrocarbons consist of only C and H atoms

  21. Alkanes (CnH2n+2) • Composed of hydrocarbon chains in which carbons are attached to one another by single bonds • Are named by the number of C in the chain and where any substitutions are found • Prefixes and the associated numbers of carbon atoms meth-1 hex-6 eth-2 hept-7 prop-3 oct-8 but-4 non-9 pent-5dec-10 22.2. Hydrocarbons consist of only C and H atoms

  22. Naming Alkanes • Find the longest continuous chain of carbons-the root. • a. Name the root by adding “-ane” to the appropriate prefix (a 4-carbon chain would be butane) b. Identify any branches, and name each by the number of carbons (a 1-carbon branch is methyl-) • a. List side chains in alphabetical order, before the root b. Use di, tri, tetra (etc…) if you have more than one of something (these do not count in alphabetizing) 22.2. Hydrocarbons consist of only C and H atoms

  23. Naming (Cont.) • Number root from side closest to the first branch • Use numbers to tell where the side chains sprout from the root • Put a dash between any number and letter or any letter and number. Use a comma between two numbers • Use the prefix “cyclo” for ring systems 22.2. Hydrocarbons consist of only C and H atoms

  24. Name the following 3-ethyl-2-methylhexane 2,3,3,4-tetramethylhexane 3-methylheptane 3-ethyl-4-methylhexane 22.2. Hydrocarbons consist of only C and H atoms

  25. Your Turn! Name the structure shown: • 1,2-dimethylpentane • 3-methylhexane • 2-ethylpentane • None of these 22.2. Hydrocarbons consist of only C and H atoms

  26. Reactions Of Alkanes • Alkanes are generally stable at room temperature • They burn in air to given carbon dioxide • When heated at high temperature they crack (break into smaller molecules) 22.2. Hydrocarbons consist of only C and H atoms

  27. Unsaturated Hydrocarbons • Hydrocarbons with one or more double bonds are members of the alkene family • open chain alkenes have the general formula C2H2n • Hydrocarbons with triple bonds are in the alkyne family • open chain alkynes have the general formula, CnH2n−2 22.2. Hydrocarbons consist of only C and H atoms

  28. Naming Alkenes • The parent chain must include the double bond • The parent alkene chain must be numbered from whichever end gives the first carbon of the double bond the lowest number • This number, followed by a hyphen, precedes the name of the parent chain, unless there is no ambiguity about where the double bond occurs • The locations of branches are not a factor in numbering the chain • Alkyl groups are named and located as before 22.2. Hydrocarbons consist of only C and H atoms

  29. Name The Following ethylene 2,3-dimethyl-1-pentene 22.2. Hydrocarbons consist of only C and H atoms

  30. Your Turn! Which name is not correct? A. B. C. D. All are correct 22.2. Hydrocarbons consist of only C and H atoms

  31. Geometric Isomers • Cis and trans isomers exist when there is a plane of a double bond or of a ring structure • cis –same • trans-opposite 22.2. Hydrocarbons consist of only C and H atoms

  32. Your Turn Which isomer is shown: • cis- • trans- • can’t tell 22.2. Hydrocarbons consist of only C and H atoms

  33. Addition Reactions of Alkenes • Alkenes undergo addition reactions that eliminate the pi-bond • CH2=CH2 + HCl(g)  Cl- CH2-CH3 • Inorganic compounds that undergo addition reactions with alkenes include: H2O, Cl2, Br2, I2, and H2. • Ozone (O3) reacts with anything that has a carbon-carbon double or triple bond, forming a variety of products 22.2. Hydrocarbons consist of only C and H atoms

  34. Aromatic Compounds • Contain a benzene(C6H5-) ring with delocalized electrons • Aromatic compounds undergo substitution reactions instead of addition reactions because of the resonance energy of the ring • example: C6H6 + Cl2C6H5Cl + HCl 22.2. Hydrocarbons consist of only C and H atoms

  35. Ethers (ROR’) • Result when both hydrogen atoms in water are replaced with alkyl groups • Are almost as chemically inert as alkanes: they burn and are split apart when boiled in concentrated acid • Are named by naming each alkyl group, alphabetically, and end with “ether” • Learning Check: • CH3OCH3 • CH3CH2OCH3 • CH3CH2OCH2CH3 • dimethyl ether • ethyl methyl ether • diethyl ether 22.3. Ethers and alcohols are organic derivatives of water

  36. Alcohols (ROH) • When an alkyl group replaces a hydrogen in water, an alcohol results • The name ending for alcohols is –ol • The parent chain must include the carbon containing the OH group • Learning Check: Name the following • CH3CH2OH • CH3CH2CH2CH2OH • ethanol • butanol 22.3. Ethers and alcohols are organic derivatives of water

  37. Oxidation of Alcohols If the alcohol carbon atom holds at least one H atom, it can be replaced with bonds to oxygen 22.3. Ethers and alcohols are organic derivatives of water

  38. Dehydration Of Alcohols: The “reverse” the the addition of water to an alkene, it is an example of an elimination reaction 22.3.Ethers and alcohols are organic derivatives of water

  39. Substitution Reactions Of Alcohols Under acidic conditions, the -OH group can be replaced by a halogen atom 22.3. Ethers and alcohols are organic derivatives of water

  40. Your Turn! What type of structure is shown • Alcohol • Ether • Peroxide • aldehyde 22.3. Ethers and alcohols are organic derivatives of water

  41. Amines • Are derivatives of ammonia where one or more hydrogens have been replaced with alkyl groups • NH3 is ammonia • CH3NH2 is methylamine • (CH3)2NH is dimethylamine and (CH3)3N is trimethylamine (bp 3oC). • Amines are bases, and react with strong proton donors to form ammonium ion-like structures 22.4. Amines are organic derivatives of ammonia

  42. Protonated Amines • Are more soluble in water than amines • Protonated amines (like protonated ammonia) are weak acids that can react with base 22.4. Amines are organic derivatives of ammonia

  43. Aldehydes • The IUPAC name ending for an aldehyde is –al • The parent chain is the longest chain that includes the aldehyde group 22.5. Organic compounds with carbonyl groups include aldehydes, ketones, and carboxylic acids

  44. Ketones The IUPAC ending for ketones is –one. The parent chain must include the carbonyl group propanone 3-pentanone 22.5. Organic compounds with carbonyl groups include aldehydes, ketones, and carboxylic acids

  45. Reactions Of Aldehydes & Ketones • Aldehydes and ketones can be hydrogenated to give alcohols • Aldehydes undergo oxidation to form carboxylic acids, while ketones strongly resist oxidation 22.5. Organic compounds with carbonyl groups include aldehydes, ketones, and carboxylic acids

  46. Carboxylic Acids The IUPAC name ending for carboxylic acids is –oic acid. the parent chain must include the carbonyl carbon, which is numbered as position 1 The common names are used for these: formic acid and acetic acid 22.5. Organic compounds with carbonyl groups include aldehydes, ketones, and carboxylic acids

  47. Your Turn! Which of the following contain a carbonyl group? • amine • amide • carboxylic acid • All contain a carbonyl 22.5. Organic compounds with carbonyl groups include aldehydes, ketones, and carboxylic acids

  48. Esters • In esters, the OH of the carboxyl group is replaced by -OR’ • Name the alkyl group attached to the O atom followed by a separate word generated from the name of the parent acid by changing –oic acid to -ate methyl methanoate ethyl ethanoate 22.5. Organic compounds with carbonyl groups include aldehydes, ketones, and carboxylic acids

  49. Preparation Of Esters Esters can be prepared by heating the parent acid with an alcohol in the presence of an acid catalyst 22.5. Organic compounds with carbonyl groups include aldehydes, ketones, and carboxylic acids

  50. Reactions of Esters • Carboxylic acids and alcohols can be obtained by heating esters with acid in a large excess of water • Esters are split apart by the action of base in a reaction called saponification 22.5. Organic compounds with carbonyl groups include aldehydes, ketones, and carboxylic acids

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