Ch 3 Review Nomenclature Organic Compounds Compounds of
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Ch. 3 Review: Nomenclature: Organic Compounds • Compounds of carbon--organic chemistry – If they have only C and H, hydrocarbons – e. g. alkanes: methane CH 4, ethane C 2 H 6, propane C 3 H 8 • general formula: Cn. H 2 n+2 – Know Table 3. 7 • Functional Groups – – R = hydrocarbon group e. g. alcohols: methanol CH 3 OH, ethanol C 2 H 5 OH e. g. amines: propyl amine, butylamine Know functional groups in Table 3. 8 Methanol (wood alcohol), CH 3 OH, is related to methane, CH 4, by replacing one H with OH.
Organic chemistry -- Chapter 20 • Introductory Topics Bonding & Structure -- Review Chapters Types of Chemical Formulas e. g. 2 -propanol (iso-propanol) 3, 9, and 10!! or fully condensed expanded structural formula condensed structural formula “line drawing” (missing C’s and H’s are understood) !!! Always FOUR BONDS to Carbon !!!
Isomerism • Isomers– different molecules with the same molecular formula Structural isomers--different pattern of atom attachment; different connectivity Stereoisomers—same atom attachments (connectivity), different spatial orientation Rotation about a single bond is not isomerism!!
Structural Isomers • Structural Isomers -- same chemical formula, but different arrangement (connectivity) of atoms e. g. C 3 H 8 O - 3 isomers (2 alcohols, 1 ether) 1 -propanol 2 -propanol ethyl methyl ether Number of possible isomers can be very large, e. g. C 3 H 8 C 4 H 10 C 5 H 12 C 6 H 14 C 8 H 18 1 2 3 5 18 C 10 H 22 C 20 H 42 75 > 105
Stereoisomers • Stereoisomers—same atom attachments (connectivity), different spatial orientation • Optical isomers (enantiomers)—are molecules that are nonsuperimposable mirror images of each other • Geometric isomers—are stereoisomers that are not optical isomers, e. g. cis and trans
Chiral Molecules • Are molecules that have nonsuperimposable mirror images – If 4 different groups are attached to carbon, it will be chiral – Chiral molecules will rotate plane-polarized light – Most physical properties are identical, but in a chiral environment enantiomers behave differently
Isomerism; Overview 7
Many Possible Compounds A Tremendous Variety of organic molecular structures and properties are possible, e. g. : vinyl chloride poly(vinyl chloride) “PVC” acetic acid aspirin
More Organic Compounds Caffeine C 8 H 10 N 4 O 2 methylamine fortunately, the subject is very systematic ! and is readily classified by “organic functional groups”
Hydrocarbons • Alkanes Cn. H 2 n+2 CH 4 methane C 2 H 6 ethane C 3 H 8 propane C 4 H 10 butane alkyl groups: methyl CH 3 CH 2 phenyl C 6 H 5 C 5 H 12 pentane C 6 H 14 hexane C 7 H 16 heptane C 8 H 18 octane, etc….
Alkane Nomenclature 1. 2. Name parent chain--longest continuous chain Number parent chain -- First branch gets lowest possible number 3. 4. Name & number branches Order branches -- Alphabetical order -- Multiple identical substituents get prefix Samples: CH 3 CH 2 CHCH 3 CH 2 CH 3 5 -ethyl-2, 4, 6 -trimethyloctane 5 -bromo-2 -cyano-4 -methylheptane (see book for detailed “rules” and other functional groups)
Reactions of Alkanes (generally unreactive) • Combustion -- fuels! e. g. C 5 H 12(l) + 8 O 2(g) --> 5 CO 2(g) + 6 H 2 O(l) • Free radical substitution (not selective!) C 2 H 6(g) + Cl 2(g) --> C 2 H 5 Cl(g) + HCl(g) • Dehydrogenation (reverse rxn is more common!) C 2 H 6(g) --> H 2 C=CH 2(g) + H 2(g) • “Cracking” of hydrocarbons (petroleum industry) at! he s d e e n ssu e r p r o t and/ a he s d e e n t! lys a t a c ds nee t! hea s d e ne re!
Alkenes ~ C=C double bond Cn. H 2 n (with one double bond) • Geometric isomers are possible, e. g. : cis-2 -butene trans-2 -butene – Restricted C=C bond rotation – Trigonal planar geometry at C=C carbons – sp 2 hybridization at C=C carbons • Nomenclature (C=C bond takes preference) CH 3 CH 2 CH=CCH 3 2, 5 -dimethyl-2 -heptene cyclohexene
Reactions of Alkenes addition to double bond RCH=CH 2 + HX --> RXCH-CH 3 + ≡ Markovnikov’s rule ~ “them that has, gets” (H goes on the C that already has the most H’s) Addition of non-polar reagents (H 2, Br 2, etc) also occurs
Alkynes ~ C≡C Triple Bond Cn. H 2 n-2 (with one triple bond) • • linear geometry at C≡C carbons sp hybridization at C≡C carbons no “cis-trans” isomers similar addition reactions to alkenes (stepwise addition can occur) XY XY
Aromatic Hydrocarbons (benzene and its derivatives) Benzene ~ C 6 H 6 • • planar 6 -membered ring (especially stable) all C-C distances equivalent sp 2 hydridization at all carbons delocalized set of 3 double bonds (6 p electrons) other common aromatic hydrocarbons: napthalene anthracenes
Aromatic Nomenclature • Aromatic ring as substituent – Phenyl (C 6 H 5–) – Benzyl (C 6 H 5 CH 2–) • Monosubstituted benzene – (name of substituent)benzene – Some common “trivial” names • Toluene • Phenol • Polysubstituted benzene – Assign numbers to substituents 4 -phenyl-1 -hexene propylbenzene 3 2 1 1 -bromo-3 -fluorobenzene
Aromatic Substitution Rxns • Substitution Reactions of Aromatic Hydrocarbons (never addition!) X 2 X = Cl, Br X 2 HNO 3 (H+ catalyst) ( NOT aromatic! ) st! ne taly a c s ed
Organic Functional Groups Family Hydrocarbons alkanes alkenes alkynes aromatic Characteristic Structural Feature Examples only single bonds C=C C≡C CH 3 CH 2=CH 2 HC≡CH benzene ring Alcohols* R-O-H CH 3 CH 2 OH Ethers* R-O-R’ CH 3 OCH 3 * structures like water
More Organic Functional Groups “carbonyl” compounds Family Aldehydes Ketones Carboxylic Acids Esters Characteristic Structural Feature Examples
More Organic Functional Groups Family Characteristic Structural Feature Examples Amines: 1º 2º 3º RNH 2 RNHR’ RNR’R” CH 3 NH 2 (CH 3)2 NH (CH 3)3 N Amides
Alcohols (organic derivatives of H 2 O) Nomenclature Alcohols, R-O-H R = CH 3 CH 2 methanol 1 -propanol (n-propanol) OH CH 3 CHCH 3 2 -propanol (iso-propanol) phenol 3, 7 -dimethyl-4 -octanol
Reactions of Alcohols Oxidation [O] primary – “H 2” aldehyde [O] secondary – “H 2” [O] ketone No Reaction tertiary [O] = oxidizing agent, e. g. Cr 2 O 72–
More Reactions of Alcohols Elimination + H 2 O H+ alkene alcohol Substitution RCH 2—OH + H—X alcohol X = Cl, Br, I – H 2 O RCH 2—X alkyl halide
Aldehydes and Ketones Nomenclature methanal (formaldehyde) propanone (acetone) ethanal (acetaldehyde) butanone (methyl ketone) propanal 5 -methyl-3 -heptanone
Reactions of Aldehydes and Ketones Hydrogenation (reduction) of aldehydes and ketones “H 2” primary alcohol aldehyde “H 2” secondary alcohol ketone Oxidation of aldehydes (very easy!) [O] aldehyde carboxylic acid
Carboxylic Acids Nomenclature of Acids methanoic acid (formic acid) ethanoic acid (acetic acid) benzoic acid CH 3 CH 2 CO 2 H (condensed formula) butanoic acid Salts of Acids Na. OH H 2 O acetic acid sodium acetate
Condensation Reactions • a condensation reaction is any organic reaction driven by the removal of a small molecule, like water • esters are made by the condensation reaction between a carboxylic acid an alcohol ü the reaction is acid catalyzed • acid anhydrides are made by the condensation reaction between 2 carboxylic acid molecules ü the reaction is driven by heat
Esters Nomenclature of Esters alkyl group acid name ethyl acetate -ate ethyl butanoate methyl benzoate Formation of Esters (from acid + alcohol) + + H 2 O
Ethers R – O – R’ CH 3 CH 2–O–CH 2 CH 3 diethyl ether CH 3–O–CH 2 CH 3 methyl propyl ether • Ether Synthesis: H+ R–O–H + H–O–R R–O–R – H 2 O
Amines (organic derivatives of NH 3) methylamine methylpropylamine dimethylamine 2 -aminohexane aniline Like ammonia, amines are weak bases: RNH 2 + H+ RNH 3+
Amides Acid derivatives (e. g. 1º amides: –NH 2 instead of –OH) + + Nomenclature R = CH 3 R = CH 2 CH 2 CH 3 ethanamide pentanamide, etc. amides (unlike amines) are generally not basic (due to e- withdrawing effect of the C=O group) H 2 O
Sample Questions (1) Write complete, systematic names for:
Sample Questions, cont. (2) Write complete, specific structural formulas for all of the organic reactants and products in the reaction. an ester Na. OH sodium acetate + 3 -pentanol (3) Show, with specific structures and reactions, how the following compound can be prepared in three steps starting with the appropriate alkyne.
Answers 1. 2 -cyano-4 -methyl-3 -heptene 2 -butylbenzoate 4 -phenylhexanal 2. Na. OH + cat, D 3. + H 2 O pressure acid cat step 1 step 2
Answers, cont. 3. , cont. [ox]
Organic Polymers -- macromolecules made up of many repeating units called monomers e. g. polystyrene is formed via the polymerization of the monomer styrene: hn n ~ 103 - 106 styrene e. g. some rings can open to form polymers: polystyrene
Methods of Polymerization Addition (very common -- works with most alkenes) CH 2=CH 2 + CH 2=CH 2 etc…. ---CH 2–CH 2–CH 2 --- = • requires an initiator (e. g. a catalyst or UV light) to start the “chain” reaction
More Methods of Polymerization Condensation (common for polyesters and polyamides) a small molecule (e. g. H 2 O) byproduct is formed X-A-Y + X-B-Y – XY Ring-Opening (uncommon except for polyethers and most inorganic polymers, e. g. silicones) etc…
Common Addition Polymers Monomer CH 2=CH 2 Polymer —CH 2–CH 2—n ethylene polyethylene CH=CH 2 —CH–CH 2— n styrene CH=CH 2 Cl vinyl chloride CH=CH 2 N≡C cyanoethene polystyrene —CH–CH 2— Cl n poly(vinyl chloride) ~ PVC —CH–CH 2— N≡C n “Orlon”
One More Common Addition Polymer! Addition polymerization of dienes “isoprene” (2 -methyl-1, 3 -butadiene) “natural” rubber
Common Condensation Polymers Polyesters + diacid diol – H 2 O polyester e. g. = = “Dacron”
Sample Question Write a complete structural formula of the organic polymer that is produced in each reaction. State whether the polymerization process is addition, condensation, or ring-opening. + HO-CH 2 -OH
Answer a. condensation b. ring-opening c. addition d. addition
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