Objective 5. Name alkanes chains and rings parent and branches.
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1 Objective 5 Name alkanes chains and rings parent and branches.
2 Organic Functional Groups Are Small Groups of Atoms With Specific Bonding and Specific Physical and Chemical Properties What Do These Functional Groups Look Like?
3 Alkanes come from: a) Plants b) Petroleum c) Both d) None outreach/plant_id/flowers_indoor/heart_philodendron.html
4 Alkanes and Cycloalkanes Contain C and H Only Hydrocarbons come from Petroleum: Petroleum components make many useful substances. Hydrocarbons come from Plants: waxes terpenes
5 CEN, 12/17/07, p. 11 Microorganisms can help squeeze methane out of oil fields The same microbes that degrade oil could allow oil companies to extract difficult-to-recover energy from oil fields and oil sands through existing infrastructures, according to a new study (Nature, DOI: /nature06484.) Biodegradation: alkanes in oil ---water---> CH 3 COO - + H 2 CH 3 COO - ---> CO 2 + H 2 CO 2 + H > CH 4.
6 Physical Properties: Hydrocarbons Are Insoluble in water. Why? Branched Alkanes have lower b.p. and m.p. than straight alkanes. As # of branches --> b.p. and m.p. (branched alkanes do not pack as close together as straight alkanes) Chemical Properties - Reactivity: Hydrocarbons are used as Fuels (combustion reaction) ΔH of combustion as # of C (per mole) Octane rating: Octane rating is not related to heat of combustion. In general, Alkanes (C-C and C-H bonds) are unreactive (polar reactions). Alkenes, Alkynes (π bonds) are more reactive. Unless light (radical reaction) is involved - activates C-H bond R-H + Cl 2 -- hυ --> R-Cl + HCl (substitution reaction)
7 Alkanes and Cycloalkanes Contain C and H Only Saturated Hydrocarbons = 4 single bonds to C (saturated w/ H) Alkane Chains Cycloalkane Rings Bigger Hydrocarbons (> C 3 ) Have Isomers: Isomers are Straight or Branched. Is an alkane chain really straight? Carbon atoms in compounds are classified as 1 o, 2 o, or 3 o 1 o = C has 1 C bonded to it 2 o = C has 2 C bonded to it 3 o = C has 3 C bonded to it
8 Objective: Classify hydrocarbons Compound A is: a. straight b. branched Compound A has carbons. Compound B has 3 o carbons. Compounds A and B are: d. same e. isomers f. different A B
9 Alkanes are used for or in: a) Fuel b) Soaps c) To make other organic compounds d) All e) None
10 Components of Petroleum Make Many Useful Functional Groups Taken from R. Chang, Chemistry, 4th ed., McGraw-Hill
11 CEN, 2/1/99, Soaps and Detergents, p. 38
12 Identify the functional group(s) in each compound Simazine: herbicide that disrupts photosynthesis but associated with potential health problems Roundup (Glyphosate): analog of glycine; herbicide that interferes with plant biosynthesis of amino acids. Less toxic than caffeine, aspirin, and table salt Physcion: fungicide boosts production of proteins and phytochemicals that are active against bacterial and fungal invaders. (S)-Metolachlor: herbicide that inhibits plant enzymes. CEN, 2/16/09, p Greening the Farm
13 Identify the functional group(s) in each compound Lindane: insecticide (neurotoxin) that kills insects that eats bark on Christmas trees and releases toxin that kills the tree. Persistent in environment. No longer used. Bifenthrin:insecticide (neurotoxin) that is less toxic and lower application rate than lindane. Synthetic analog of natural insecticidal pyrethrin compounds produced by plants. CEN, 2/16/09, p Greening the Farm
14 10/11/10, Of the hundreds of volatile compounds in raw peanuts, only 11 contribute to peanut aroma 27 compounds contribute to nutty smell of roasted peanuts. a common aroma noted in popcorn, crusty wheat bread, and basmati rice caramel-like fragrance
15 10/10/11, CEN, p. 15 Lipidomics 8 Classes of Lipids (LIPID MAPS) based on lipid backbone. One example from each class is shown here, with the class name and the common name. Saccharolipids and polyketides are found only in plants and bacteria. The others are found in all organisms.
16 Antibiotics are classified by structure: ( Beta-lactams Aminoglycosides Tetracyclines Rifamycins Macrolides Polypeptides Chloramphenicols Synthetic antibacterials β-lactam ring Amino sugar Tetracycline
17 4/15/13, CEN, Rapid Route To Pactamycin, p. 8 Pactamycin (from bacterium Streptomyces pactum) has antimicrobial, antitumor, antiviral, and antiprotozoal properties. It disrupts early steps in protein synthesis in bacteria, cancer cells, and mammalian cells.
18 Organic Names are Based on the Number of Carbons # of C Formula of Chain Name 1 CH 4 Methane 2 C 2 H 6 Ethane Formula of Ring Name 3 C 3 H 8 Propane C 3 H 6 Cyclopropane 4 C 4 H 10 Butane C 4 H 8 Cyclobutane 5 C 5 H 12 Pentane C 5 H 10 Cyclopentane 6 C 6 H 14 Hexane C 6 H 12 7 C 7 H 16 C 7 H 14 Alkane - 1 H = Alkyl group = R. Attach functional group to R E.g., CH 4-1 H = CH 3 CH 3 OH methane methyl group methyl alcohol (methanol)
19 Objective: Name hydrocarbons What is the name of this hydrocarbon? a) 4-ethyl-5-methylhexane b) 2-methyl-3-ethylhexane c) 3-ethyl-2-methylhexane ID parent chain: longest continuous chain = hexane ID branches: alkyl groups = ethyl and methyl (alphabetical order) Number the carbons in the parent chain from one end to the other: use lowest numbers.
20 Objective: Name hydrocarbons What is the name of this hydrocarbon? a) 4-ethyl-5-methylhexane b) 2-methyl-3-ethylhexane c) 3-ethyl-2-methylhexane ID parent chain: longest continuous chain = hexane ID branches: alkyl groups = ethyl and methyl (alphabetical order) Number the carbons in the parent chain from one end to the other: use lowest numbers.
21 Objective: Name hydrocarbons What is the name of this hydrocarbon? Enter your choices in your desired sequence. Include numbers on parent chain for branches, commas, and dashes as needed. E.g., 2,3-dimethyl hexane is 2,3-kgc. a. butane g. methyl b. pentane h. ethyl c. hexane i. propyl d. heptane j. butyl e. octane k. di f. nonane l. tri ID parent chain: longest continuous chain = hexane ID branches: alkyl groups = ethyl and methyl (alphabetical order) Number the carbons in the parent chain from one end to the other: use lowest numbers.
22 How are Drugs named? Where do Drug names come from? Behind every generic name lies a specific process
23 Chemical Formula gives info about # of π Bonds and Rings The # of H s relative to C tells us the Hydrogen Deficiency Index (Degree of Unsaturation) Formula HDI = # of π Bonds # of Rings Example C n H 2n Alkane chain = fully saturated C n H 2n 1 0 Alkene chain C n H 2n 0 1 Cycloalkane C n H 2n Alkyne, C n H 2n C n H 2n Cycloalkene C n H 2n (2n+2) - (# of H s in formula) 2 C n H 2n-4 C n H 2n-6 Benzene where n = # of C
24 Objective: Relate formula to HDI to help you with structure Hydrogen Deficiency Index (Degree of Unsaturation or HDI) tells you the number of pi bonds or rings in a chemical formula. Saturated hydrocarbon chain (alkane): C n H 2n+2 Unsaturated hydrocarbon chain (alkene, alkyne, aromatic): fewer H s than alkane For hydrocarbon: HDI = 1/2 (H s in fully saturated - H s in chemical formula) E.g., C 3 H 8 is a saturated hydrocarbon chain. n = 3 HDI = 1/2 (8-8) = 0 so NO pi bonds or rings
25 Objective: Relate formula to HDI to help you with structure Hydrogen Deficiency Index (HDI) tells you the number of pi bonds or rings in a chemical formula. Remember: Saturated hydrocarbon chain (alkane): C n H 2n+2 For hydrocarbon: HDI = 1/2 (H s in fully saturated - H s in chemical formula) Index # of pi bonds # of rings
26 What if a compound has X (F, Cl, Br, I), O, or N? Hydrogen Deficiency Index rules: Treat X the same as H (replace X with H) Ignore O For each N, omit the N and one H Examples: C 6 H 12 ==> fully saturated C 6 is C 6 H 14 so Index = 1/2(14-12) = 1 So C 6 H 12 has 1 pi bond or 1 ring. C 6 H 6 C 3 H 5 Cl ==> same as C 3 H 6 so Index = 1/2(8-6) = 1 C 3 H 6 O C 2 H 7 N
27 Name or draw the structure of the following compounds. Identify the 1 o, 2 o, and 3 o carbons. a. C 6 H 12. Does this formula have any isomers? If so, draw an isomer. Name each isomer. b. 2,3-dimethyl-4-ethylcyclohexane c. d. (CH 3 ) 2 CHCH 2 C(CH 3 ) 2 CH 3
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