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Organic Chemistry Chem 2014. Organic Chemistry Organic Chemistry: - the chemistry of carbon and carbon-based compounds - (C – C or C – H or C – R) - (can.

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Presentation on theme: "Organic Chemistry Chem 2014. Organic Chemistry Organic Chemistry: - the chemistry of carbon and carbon-based compounds - (C – C or C – H or C – R) - (can."— Presentation transcript:

1 Organic Chemistry Chem 2014

2 Organic Chemistry Organic Chemistry: - the chemistry of carbon and carbon-based compounds - (C – C or C – H or C – R) - (can be a few to hundreds of carbons covalently bonded to one another) Characteristics of Organic Compounds: *Usually have strong odors and low boiling points * Most do not conduct electricity * Most will ignite and burn * Slower rates of reactions

3 Smells & tastes: fruits, chocolate, fish, mint Medications: Aspirin, Tylenol, Decongestants, Sedatives Addictive substances: Caffeine, Nicotine, Alcohol, Narcotics Hormones/Neurotransmitters: Adrenaline, Epinephrine Food/Nutrients: Carbohydrates, Protein, Fat, Vitamins Genetics: DNA, RNA Consumer products: Plastics, Nylon, Rayon, Polyester Organic Chemistry in everyday life:

4 Animals, plants, and other forms of life consist of organic compounds. – Nucleic acids, proteins, fats, carbohydrates, enzymes, vitamins, and hormones are all organic compounds Besides carbon, the most common elements in organic compounds are hydrogen, oxygen, nitrogen, sulfur, and the halogens. – All of the preceding elements are non-metals, therefore organic compounds have covalent bonding.

5 Copyright © Houghton Mifflin Company. All rights reserved. 14 | 5 Numbers and Types of Bonds for Common Elements in Organic Compounds Application of the octet rule indicates that these elements should bond as shown below: Section 14.1

6 Review: Octet Rule Rule of Eight – elements want either 8 or 0 electrons in its outermost level (except for H and He which want 2 or 0) Each energy level can only hold a certain number of electrons. 1 st level2 electrons 2 nd level8 electrons 3 rd level8 electrons 4 th level 18 electrons

7 *Helium only has 2 valence electrons Group NumberNumber of Valence Electrons Periodic Table and Valence electrons

8 Let’s Practice Bohr Diagrams Energy Levels Diagram HW wkst

9 Lewis Structure Placing valence electrons around element symbol to decipher bonding patterns

10 Lets practice Lewis dot structures

11 Practice Lewis Dot Structures 1. Oxygen (e = _________)2. Potassium (e = _______)3. Bromine (e = ________) 4. Germanium (e= ______)5. Aluminum (e = ______)6. Phosphorus (e = ______)

12 Big Idea in Organic Chemistry Structure controls Function Each functional group has predictable reactivity = atom or group of atoms that gives characteristic chemical properties to a class of organic compounds

13 Drawing Organic Structures Butane: C 4 H 10 CH 3 CH 2 CH 2 CH 3 CH 3 (CH 2 ) 2 CH 3 Shortcuts make structures easier & faster to draw Line Structure Carbon Skeleton Only shows bonds C atoms assumed at each end and intersection of bonds H atoms not shown Assume 4 bonds to each C Fulfill C’s 4 bonds by adding H’s Lewis Structure Structural formula Condensed Structures molecular formula Carbon Atoms

14 Types of Organic Compounds Classified according to functional group Alkane Alkene Alkyne Halocarbon Alcohol Ether Ketone Aldehyde Carboxylic acid Amine Amino acid Amide Hydrocarbons (H & C only) Ester

15 Characteristics and Examples Hydrocarbons AlkaneAlkeneAlkyne Contain C – C single bond C = C double bond C ≡ C triple bond Formula n is # of carbons C n H 2n+2 C n H 2n C n H 2n-2 Naming Prefix (# of C’s)- ane# (count from smallest direction of =) – Prefix (# C’s) - ene # (count from smallest direction of ≡) – Prefix (# C’s) - yne Examples See followingSlides forexamples Linear/ skeletal structure \/ \

16 Organic Prefixes Meth- 1 carbon Eth- 2 carbon Prop- 3 carbon But- 4 carbon Pent- 5 carbon Hex- 6 carbon Hept- 7 carbon Oct- 8 carbon Non- 9 carbon Dec- 10 carbon

17 Examples Name Molecular Formula Lewis/ Structural Formula Condensed Structural Formula Linear propane C3H8C3H8 CH 3 CH 2 CH 3 \/ ethane C2H6C2H6 CH 3 \ 2-pentene C 5 H 10 CH 3 CHCHCH 2 CH 3 2-buteneC4H8C4H8 CH 3 CHCHCH 3

18 Name Molecular Formula Structural FormulaCondensed Structural Formula 3-heptyne C 7 H 12 CH 3 CH 2 CCCH 2 CH 2 CH 3 1-propyneC3H5C3H5 CHCCH 3

19 Copyright © Houghton Mifflin Company. All rights reserved. 14 | 19 Alkanes – Energy Related Products Methane = primary component of natural gas Propane & Butane = primary component of bottled gas Gasoline = pentane to decane Kerosene = alkanes with n = 10 to 16 Alkanes with n > 16  diesel fuel, fuel oil, petroleum jelly, paraffin wax, lubricating oil, and asphalt Section 14.3

20 Copyright © Houghton Mifflin Company. All rights reserved. 14 | 20 Organic Compound Nomenclature Due to the large number, variety, and complexity of organic compounds, a consistent method of nomenclature has been developed. Section 14.3

21 Copyright © Houghton Mifflin Company. All rights reserved. 14 | 21 IUPAC System of Nomenclature For Alkanes Compound is named as a derivative of the longest continuous chain of C atoms. Positions & names of the substituents added – If necessary, substituents named alphabetically – More than one of same type substituent – di, tri, tetra The C atoms on the main chain are numbered by counting from the end of the chain nearest the substituents. – Each substituent must have a number. Section 14.3

22 Hydrocarbons wkst

23 Names of Linear Alkanes and Alkyl Substituents Alkane Alkyl substituents # of C atoms CH 4 CH 3 CH 3 CH 2 CH 3 CH 3 CH 2 CH 2 CH 3 -CH 3 -CH 2 CH 3 -CH 2 CH 2 CH 3 Methyl Ethyl Propyl etc. Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane Root: number of C atoms Suffix: functional group (-ane for alkanes) (-yl for alkyl groups)

24 Copyright © Houghton Mifflin Company. All rights reserved. 14 | 24 An Example to Consider The longest continuous chain of C atoms is five Therefore this compound is a pentane derivative with an attached methyl group – Start numbering from end nearest the substituent – The methyl group is in the #2 position The compound’s name is 2-methylpentane. Section 14.3

25 Copyright © Houghton Mifflin Company. All rights reserved. 14 | 25 Drawing a Structure from a Name An Example Draw the structural formula for 2,3-dimethylhexane. Note that the end name is hexane. Draw a continuous chain of six carbon (C) atoms, with four bonds around each. Section 14.3

26 Copyright © Houghton Mifflin Company. All rights reserved. 14 | 26 Drawing a Structure from a Name An Example (cont.) Number the C atoms from right to left. Attach a methyl group (CH 3 --) to carbon number 2 and number 3. – Add necessary H atoms. 2,3-dimethylhexane Section 14.3

27 Copyright © Houghton Mifflin Company. All rights reserved. 14 | 27 Drawing a Structure from a Name Confidence Exercise Draw the structural formula for 2,2,4-trimethylpentane. Note that the end name is pentane. Draw a continuous chain of five carbon (C) atoms, with four bonds around each. Section 14.3

28 Copyright © Houghton Mifflin Company. All rights reserved. 14 | 28 Drawing a Structure from a Name Confidence Exercise (cont.) Number the C atoms from right to left. Attach two methyl groups (CH 3 --) to carbon number 2 and one to number 4. Section 14.3

29 Copyright © Houghton Mifflin Company. All rights reserved. 14 | 29 Drawing a Structure from a Name Confidence Exercise (cont.) Add necessary H atoms. 2,2,4-trimethylpentane Section 14.3

30 CH H H H Methane CH 4 H C CCC H H H H HHH H H Butane C 4 H 10 Butyl -C 4 H 9 Methyl -CH 3 CH H H ? R H C CCC H H H H HHH H ? Where R = any other C atom or arrangement of C atoms R

31 H CH H H C CC H H HHH C H H H 2 - methylbutane Example of R group Expanded Structure Line Structure

32 First Ten Hydrocarbons: Properties Name Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane CH 4 C 2 H 6 C 3 H 8 C 4 H 10 C 5 H 12 C 6 H 14 C 7 H 16 C 8 H 18 C 9 H 20 C 10 H 22 Number of Carbon Atoms Molecular Formula Melting Point, o C # of Isomers Boiling Point, o C

33 Properties of Alkanes Compound Methane Ethane Propane Butane Pentane MW Boiling point (°C) Linear Alkanes: C atoms: gas at room temp C atoms: liquid at room temp >15 C atoms: solid at room temp Larger molecular weight → Stronger London dispersion forces Nonpolar → only London Dispersion Forces IMF Formula CH 4 C 2 H 6 C 3 H 8 C 4 H 10 C 5 H 12

34 Naming Branched Alkanes (IUPAC) 1.Root name: name of longest continuous C chain (parent chain) 2 equally long? Choose the one with more branches 2.Number C atoms in chain, starting at end with first branch 3.Identify substituents, give each a number (C it is connected to) Two or more identical substituents: use prefixes (di-, tri-, tetra-, etc.) 4.List substituents alphabetically before root name Do not alphabetize prefixes 5.Punctuation:commas separate numbers from each other hyphens separate numbers from names no space between last substituent & root name 4-ethyl-3,5-dimethyloctane ethyl 3-methyl and 5-methyl = 3,5-dimethyl Octane

35 Copyright © Houghton Mifflin Company. All rights reserved. 14 | 35 Alkenes are very Reactive and are termed “unsaturated hydrocarbons” Alkenes will characteristically react with hydrogen to form the corresponding alkane. Section 14.3

36 Copyright © Houghton Mifflin Company. All rights reserved. 14 | 36 Alkynes are Unsaturated Hydrocarbons Due to the triple carbon bond, each alkyne molecule can react with two molecules of hydrogen. Section 14.3

37 Chapter 26 Hydrocarbon Derivatives

38 Hydrocarbon Derivatives Derivatives = molecules that contain C and H, as as hydrocarbons, but also contain other elements derivatives depend on their functional groups which are atoms or group of atoms that give the derivative its characteristic chemical behavior

39 Derivatives Alkane Alkene Alkyne Halocarbon Alcohol Ether Ketone Aldehyde Carboxylic acid Amine Amino acid Amide Esters

40 Halocarbon DefinitionOne or more of hydrogen atoms replaced with a member of halogen family General FormulaR – X R symbolizes the hydrocarbon portion X symbolizes the halogen atom X can be F, Cl, Br, or I Naming (IUPAC) 1. Name hydrocarbon portion 2. Add prefix to indicate halogen, add -o 3. # of halogen placement PropertiesPrimarily non polar Low boiling points Insoluble in water Soluble in hydrocarbon solvent Structure ExamplesCFC’s –chlorofluorocarbons Methanol (aerosol cans, refrigerate gases) Pesticides Dry cleaning chemicals

41 Alcohols DefinitionOne or more of hydrogen atoms replaced with a member of hydroxyl group (-OH) General FormulaR – OH R symbolizes the hydrocarbon portion OH – hydroxyl group Naming (IUPAC) Suffix –ol added to hydrocarbon root Properties*Similar to water (OH) *Up to 4 C are soluble in water *Higher boiling points *Can be –diol (2 –OH) or –triol (3 -OH) Structure Examples MethanolEthanol – grain alcohol Butanol

42 DefinitionOxygen atom that is bonded to two carbon atoms General FormulaR – O – R’ R and R’ → hydrocarbon chains -O- → functional group Naming (IUPAC) 1. Suffix –oxy added to smaller chain bonded to central oxygen atom, remainder is named as before 2. Or use similar name: add suffix –yl to each hydrocarbon and add ether PropertiesOxygen creates slightly polar region Some smaller molecules are soluble in water No H bonds so lower boiling points than alcohol but higher than hydrocarbons Structure Examples Ethers

43 Worksheet Review

44 Definition-oxygen atom bonded to single carbon atom by a double bond -called a carbonyl group (C=O) Aldeyde has carbonyl group attached to end of hydrocarbon chain General FormulaR – CHO Naming (IUPAC) Add suffix –al to the root name PropertiesMore polar than hydrocarbons Higher melting and boiling points than hydrocarbons Lower melting and boiling points than alcohol Structure Examples-Methanol (HCOH) = formaldehyde – used to make polymers and used to be used for biological preservation – found to be carcinogenic -Used as flavorings in food and candy and as fragrances in inhalants and perfumes -Vanilla flavor in ice cream and cinnamon in hot chocolate Aldehydes

45 Ketones DefinitionKetone has a carbonyl group on the interior of a hydrocarbon General FormulaR-COR’ Naming (IUPAC) Add suffix –one to the root name Name must include which C it is attached to b/c always on interior C when a Ketone PropertiesMore polar than hydrocarbons Higher melting and boiling points than hydrocarbons Lower melting and boiling points than alcohol Structure Examples-Propanone (CH3COCH3) = acetone - volatile liquid and vapor is flammable -Cortisone= hormonal response to fight or flight, treatment of severe allergic reactions; too much bad b/c breaks down connective tissue, increases production of stomach acid and decreasing protective mucus membranes resulting in gastric ulcer

46 Worksheet Review

47 DefinitionCharacterized by presence of a carboxyl group General FormulaR – COOH Naming (IUPAC) Prefix + -anoic acid Properties-carboxyl end is very polar making it soluble in water -higher boiling points than hydrocarbons Structure Examples (see also book pg 852) -Fatty acids -Formic acids (simplest form HCOOH) – from ants -Acetic acid – (CH3COOH) – responsible for sour taste of vinegar -lactic acid – responsible for sour cow’s milk Carboxylic Acids

48 DefinitionSimilar to carboxylic acid, but has hydrocarbon group in place of H atom of carboxy group General Formula R-COOR’ Naming (IUPAC) -named for the alcohol and acid from which they are produced -alcohol name (suffix changed to –yl) + acid name (suffix changed to –oate) Example : ethanol + propanoic acid = ethyl propanoate OR -alcohol name (-yl) + acid (-ate) = propyl alcohol + formic acid = propyl formate Properties-polar but do not form H bonds with each other -boiling points are lower than BP of similar alcohols or acids -distinctive odors based on alcohol and acid reaction (typically fruity odors) Structure Examples (see also book pg 856) Ester

49

50 Worksheet Review

51 DefinitionContains an amino group (-NH2) attached to hydrocarbon chain General FormulaR-NH2 2◦ = R-NHR’ 3◦ = R-NR’R” Naming (IUPAC) -add suffix –amine to root name of hydrocarbon Properties-amino group is polar -higher boiling points than HC but lower than alcohols -weak bases Structure Examples-amino groups found in DNA, vitamins, anesthetic drug -basis of nicotine, cocaine, amphetamines -unpleasant odors = cadaverine produced by bacteria on decaying organisms – can cause food poisoning -found in suntan lotion Amines

52 DefinitionAmino group attached to carbon of carboxyl group General FormulaR-CONH2 Naming (IUPAC) -add suffix –amide to root of hydrocarbon Properties Structure Examples Amides nylon and urea, which exist in chains, and caffeine, which exists in a ring

53 Worksheet Review


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