01 Alkanes set

01 Alkanes set - Chemistry defined as: a study of MATI'ER,...

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Unformatted text preview: Chemistry defined as: a study of MATI'ER, as opposed to ENERGY,which is Physics. Although the two now overlap one another; because: Characteristics (Properties) of Organic Compounds ’1. Combustibility E = Amc2 . . 2. Volatility 3. Solubility (in water) "like dissoives like" 4. Conductivity (of an electric current) [vaporizers] Chemistry studies matter, with respect to: (1) composition, (2) structures, and (3) changes A problem: an unknown substance; white, powder (e.g. salt vs. sugar); how composition can be merely the "molecularformula"; e.g. H20, H2804, NaCl, could you determine whether it is organic or inorganic“? CEH1205, etc. The above properties are related primarily to two aspects of chemical compound: structure brings in a three—dimensionality aspect: 1. Bonding 2. Structure (MODELS WILL Consider: "left—handed" -ness"and "right—harded" -ness"— BE HELPFUL!!) (a) ionic. or (a) polar,or (b) covalent (b) non-polar Some SciFi stories:-—involve some "mirror in age" phenomena..... CEH1205 has 16 different isomers, only ONE of which is the glucose It is the one whose "structure" our bodies can metabolize. IUIIIE Elmdlng :traracte-‘uefihya transfer oleleclrorils). ions are lurrriecj I ions are spherical. therefore non-directional [or omn:-dirocto"ial] covalent bonds areformed by Sharlng eleCtronls) ions are E: formed, but molecules instead molecules are NOT charged; but they have definite SHAPESH e.g. 1» Moiron-clacl rulesll a H2 so 16mm. HE? 1-2:]:‘15 J 01- + -Cl —1-Clg QB consider: —i@ . [Gpln —:- +1Ions Fl H—C—H CI U “1+ _ “1419 + 3 —1-- VIEI 5'2 Ill H Y a U 1+ 2— _ I Ca r Cl} _... (:3 (3,2 non polar poar LIKE DISSOLVES LIKE (S _ '3 . 1,:‘2 Eb—J— ha C? Ionic bonds are usuallyI formed when combining elements from the far left side . . . consider: The Ammonia Fountain of the PeriodicTehle with elements from the far right side; {n_ot counting tl'iinert gases. of cwrsel 1.05 Rules for writing organic structures: (remember--a dash between atoms represents a pair of electrons: e.g. A._. 3 Consider the following possible written assignment: - 33“ C atom form 4 Covalent bonds? 99- CH4 . Eac' -l atornforms 1 covalent bond; e.g. see above, and l-l20 Writing Lewis (e ectron-dot) structures (use only outer-shell electrons _ 38C 0 atom forms 2 covalent bonds: eg see above and different symbols for electrons of the different elements) he 0 forms only1 covalent bond, itvvill have a minus charge; e.g. 0He if) BFs the 0 forms 3 covalent bonds, itvvill have a plus charge; e.g. H30 G) atom forms 3 covalent bonds; e.g. NH3 he N forms only2 covalent bonds, it will have aminus charge; e.g. NH2® he N forms 4 covalent bonds, it will have a plus charge; e.g. NH4 @ 5. Eacr halogen atom (F, Cl, Br, I) forms1 covalent bond; e.g. CCI4 Anything you can write that does not vioiate any of the above ruies is a bona gig organic compound. STRUCTURE OF MEI'HANE But, first, consider the covalent bonc ir H-F H has one is electron; F has 9 electrons: is 2, 252, 2p5 orbital H bridization 25 2px 2py 2p: a 2s electron is "promoted" to the 2p: orbital, giving rise to a hybridized carbon atom which 3 E E E has four equivalent electrons. sp3 hybridization; |n methane, CH4 , the carbon atom forms 4 eguivalent carbon-to-hvdrogen bonds tetrahedral shap 0 But C has only 6 electrons: is 2, 2s2, 2p2 _ _ _ _ Fm bond angles = 109.5 . . i ll internal angles should be a CH2 vvith tvvo sigma bonds 0 re 109.50 at right angles, but none has ever been / '-—-—. isolated. "he simplest organic cmpd regu|ar tetrahedron; \ is CH4 vvith FOUR equivalent OH . . . bondg WW? four identical Sides Hydrocarbons allphatlcs—I— aromatics RLKANES ALKENES ALI-{WES ALIEYELIC$ Paraffins saturated [Chap 4, p. 129 is on Alkanes} All alkanes haue formula: Cnflzn + 2 Table 4.3, p. 135 lists some "UH-branched alkanes. Their formulas are: CH3 {CH2 3" CH3 G reek prafl Ill-E start here lr Their names: methane, ethane. propane, butane. ane; They form an homologous series Iultrl1ich differs by a"metl1ylene group". 1.1- Each different kind of hydrogen gives a different ALKYL group methane CH4 4:0: therefore only ONE methyl group methyl group methyl methyl chlori d e alcohol ethane CH3CH3 CHSCHE- CH3CH2—Br CHSCHTOH CgHa ethyl group 512], therefore oniy ONE ethyl group propane CH3 CHECHg F552E therefore TWO propyl gro u ps Did you catch it? alkrflE becomes all-tYL Can you name them?? GH30H2CH2 — the normal propyl group CH30HCH3 I This is on p. 1353 the ieopropyl group In Fm" text" A closer look . .. Identify the primary (10 ),secondary (2°), and tertiary (3°) carbons and hydrogens . . . "I' H H H — C — H | | | H—c—c—H || HH C2 H6 HHHH |||| H—C—C—C—C—H | | | | H H C4H10 The BIG question: What is the ratio of the different kinds of hydrogens in each of the alkanes above?? C4 But what about the TWO butane-s??? C-I3CH2CHEC ,.-"' tt-e n-lJutyl group- byre'not figs primary II from elthsr one of a normal alltaoe (f CH3°H2°H2¢H3 --..,. stays-43.? HC 43 C H cillm 4 1D 'I n-tILtans hum" E: E- 4 - therefore TWCI ihe'fi' 3“! 7W3 . olfferern alkyl grnps _ difiarnl tula-‘Ies ' CTIgCHCFly— If" a I he lsohutyl group - 2y removing a primary 3 H from the unhrenclled end ol' en lso flkm e. tl'e sec-lrulyl group; E-=|'II:E'1hE'E' are [cur -:len‘.icelsec-l1‘s; no unhiguilyl "“ o Hyocha CH3 Cal—l1 :I islla LII um; '31 -rhr:re*'.1rr: 'tl'tlfl l'lll'LErfllrll alkyl groups. ul!:|| "at Cl‘yéCHg Ihe ten-hutyl group - sinttl there is only I . CINE tsn- hydrogen in .ery i-‘1‘Ie tulewes. Ch] 1here is no ambiguity. [What about the pe ntanes? ? ‘9'} NOW- the Pemanfi: (C 5H12I There are THREE of them: 1-13 1 C—C—C—C—C—X the n—pent’yl group CH3CH2CH2CH2CH3 _____ "i C_C_C_C_C n—pentane >I{ 5:4:2 therefore ‘ C—C—C—C—C THREE differen alkylgroups }|{ (NO comm on n ame) (NO comm on n ame) X—C— C— C—C C— C— (3— (3—K CH3? C is ope ntane X (NO common name (I: the isopentyl group C —C—C 5:3:2 :1 t ere (NO common name] | FOUR differen a C the tert-pentyl group ('3 3 CHg—CIZ—C C 3 neopentane 12 : D herefore only ONE alkyl group —C—}{ the neopentyl group Some assignments for your consideration: Consider the C5H14 hexanes; --how many isomers? The ratios of their different hydrogens? (These give rise to the different hexyl groups.) Which have "common names"? What are the IUPAC names of ALL of them? An interesting exercise: A CORRECT structure can be written from an INCORRECT name. Then, write the structures from the following "incorrect" names, and give each a CORRECT name. . n-propyl t-butyl methane . isopropyl t-butyl methane . isopropyl isobutyl methane Example: | . isobutyl t-butyl methane —} CL CL CL CL (I32_c1 . sec-butylt-butyl methane I | I f. t-butyl isoamyl methane C H C g. t-butylt-amyl methane h. sec-butyl t-amyl methane (NOTE: amy.‘ is the same as pentyi) 2,2,5-timethylhexane Section 4.3: p. 134 IUPAC Nomenclature of Alkanes {and aliryl halides and alcohols, too} ill- (but l‘irstI you must know the 'con'lmon" names of the simple alkyl groups} 1 . Locate the longest continuous chain of carbon atoms: this chain determines the PARENT name for the alltane. 2. Number that chain. beginning from the end nearer any subtituentlfsi. 3. Use those numbers to designate the location ofthe substituentts}. 4. EACH substituent must be given a number. List the sub stitu ents HIPHEHEHCHHFI If the substituent occurs more that once1 use the Greek prefixes: o‘f-, as, tetra, etc. [It ts also correctto list the substituents in order ofincreasing SIZEE or of INCREASING COMPLEXITY.) 5. When branching first occurs equidistant from either end, cheese the name that gives the tower number at the first point of difference. 6. When two chains compete as the PAR ENT chain. choose the chain with the greater number of substituents. See examples on the pages that follow . . . While we're at it, whtlr not learn the nomenclature of alien halides AND of alcohols, too? LET'S DO IT!! Sec. 4.3E. p. 139 f, forAlityrl Halides CI‘IBGHQ Ci CHECHECHEF r common: ethyl chloride n-propvl fluoride isopropvl bromide IUF'AC: chloroethane 1-fluoro propane 2-bromo propane ll|3H3 CH3 common: tert—butyl bromide tubutvl bromide IUF'AC: 2-bromo-2—methvlpropane i-bromo-2,2—dimethvlpropane ne op entvl bro mide 1.15 Sec. 4.3F, p. 139 for Nomenclature offllcohols ' Fr :1 Lt Ir' 1 Consider the example: (EH3CH2timCH2CH2C Hz—DH CH3 4-methy'l-1-hexa n ol not: SmothyI-fi-he xanoi oHfl—oH CH3CH2-DH CHECHECHE—DH CHal‘fH cI-I3 OH methyl at I n-pro pyl Is opropyl alcohol ell-30 Ell alcohol alcohol lU FAG: methanol eth an ol pmpanu: 2-;1 m. p an 9| ED l'l'll‘l‘IDl'I: 1.19 c C— C— C— C— C C— C— C— C— C 0H 0H 2-pentanol 3—pentanol C—C—C—C—C—CIH C—C—C—C—C —:I- mpenty‘l alcohol n-pentane n—amyl alcohol pentane 1—pentanol c—c—c—c—oH 0H ' | t-pent‘yl alcohol C—[IZ—C—C t-amy‘l alcohol [3 2—methyIQ-h utanol C isopentyl alcohol isoamyl alcohol 3-methyI-1—hutanol 0H 0H C I I isopentane C- {I} C— C— C— C— C— C 2—methylhutane C C 2—methyl—1-hutanol 3—methyl—2—hutanol C—C—C—C —:I- C —'-"' C—[lfi—C—OH neopentyl alcohol & 2,2-dimethyl-1-propanol There are 8 isomeric pentyrl alcohols!! neopentane 2,2-dimethylpropane 11E Mew pmmem 4_5, p, 14D {as modified}: Give "common" AND IUPAC names for ALL the isomeric C4H1fl0, MID C5H120 alcohols. (NOTE: not all 5 pentanols can have "common" names, but M can have IUPnC names. (3— C- D-G-OH C-C— [3- C} _ _ _ 3., I C C C I: n—hutylalcohol DH "LEE? 1—b utan ol sec-h utyl alcohol 12—h utan oi C — C — C '5': (I: (I: “"3" 0-C“C- oH o- (3— 0H ' | h | immune Iso butyl a co 0 C 2-methyl—1-prop an ol terabum an; ohm E-m ethylpro pane 2-methyl-2—prop a nol Sec. 4.4, p. 141 Nomenclature of Cycloalkanes 4.4.11. Monoc'yclic Compounds: Simply count the carbons; then add the prefix: 'cyclo. lfthere are suhstituents, count in the direction that gives them the lowest set of numbers. List them alphabetically [or in order of increasing complexity.) [ :3: lo pentane cyclohexane cyclopro pane cyclohutane CH3 HCH3 CH3 "you have trouble naming these, look on p. 1412; in your text. ALKANES Source: petroleum, refining, cracking . . . Hydrocarbons Aliplhatic —I— Aromatic ALKANES ALKENES ALKYNES ALICYCLICS also known as: general formula: CnH2n+2 CHI—l2" CnH2n -2 I l | | ALKANES ALKENES ALKYNES ALICYCLICS Paraffins Olefins Acetylenes Paraffins Oiefins A OGIyienes cycle-whore ver saturated unsaturated unsaturated I — CZC— — CEC— — (I3— I | However, there are TWO rather important reactions of alkanes: 1. Combustion an2n+2 + 02 4f§L H20 + coz + HEAT Bunsen burners, gas and oil heaters, gasolines . . . Do you understand "octane numbers"? “3 EH3 CH 3 CH 2 H CH 3 H3 "isooctane" IUPAC?? CH3CH20H2CH2CH20H2 CH3 n—heptane REACTIONS OF ALKANES + water A. + acids —:v + bases —:- N I R- + oxidizers —‘.'t- + reducers é What does "paraffin" mean? 2. LCFH light-Catalyzed Free Radical [Halogenations] pp. 435 ff e‘Q- phbtgn + CH4 + m2 spark CHECI2+ HCI utilghi CHCI3 1- Hill h1' och + Hm NOTE: oatatyzod by light or heat or IJ.‘.|'. light. RADICAL$ are involved. Radio ale are NUT CHARGED Radicals have an UNPAIRED electron. It is a SUBSTLTUTIIDN reaction; i.e., something goes 0N, something comes 0FF. Mechanism for the LCFR chlorination of methane - . heat The Reaction. CH4 + CI2 W- CH3CI + HCI Mechanism: .u.". h t .u. u. Step1:Chainlnitiation -F_|-_C_|- .El + ._C_I. A homoly‘tic cleavage; -- two chlorine radicals are formed. Step2 H_c..H +13]: _;.. H—c- + H:E:'I: A Step 2: a chlorine radical abstracts a hydrogen atom; -- producing a methyl radical and hydrogen chloride. Step3 H_c. + :Ellé-Il a H_C:6l: + .!l A Step 3: a methyl radical abstracts a chlorine atom; -- producing methyl chloride and a chlorine radical then 2, 3, 2, 3, 2, 3, 2, 3, 2, 3, 2, 3, 2, 3, 2, 3, 2, 3, etc. etc. Steps 2 and 3 are called "Chain Propagation " steps. WHY? As one radical is used up, another radical is produced!! Selectivity of attack ip. 444] C o nsider tillilL‘iIr the MD M III-chlorinated prod u cts: CH3-CH—CH3 cg CHa—CH—GHZEI + :31 I 3—C—CH3 3:“ light i I'm I 3 3 cm3 25°c _ Isobutyl chloride Lbutyt mimic” {63%3 [37%] The product ratio is about 2 '_ 1 Which product formed faster, - - isobtltyl chloride or t-butyl chloride? There are 9 primary hydrogens but only ONE tertiary hydrogen. Then, statistically, the product ratio should have been 9: 1. Then1 the tertiary hydrogen was reacting 4.5 times FASTER than the primary hydrogens. tsobutan e Experimentally ithas been shown that: 3° =- 2“ =- 'l':I 4.43 3.25 1 l: with Br: , the product is about 99% te rtiary} 'i' 'i' Step4 |-|—c- + IE“ #- H—E:El: A methyl radical combines with a chlorine radical; -- producing methyl chloride. 'i' 'i' 'i'? Step5 H—C' + 'C—H —:- H—C—C A l!. A ll. Two methyl radicals combine; producing ETHANE! —H Step6 :Cl' + .Cll % :CI:C|: Two chlorine radicals combine; producing a chlorine molecule. Steps 4, 5, and 6: called "chain termination" steps. WHY? Because each uses up TWO radicals, and generates NONEll This causes the chain reaction to SHUT DOWN! AND NOWI ON TO CYCLOALKANES Butfirst, aword about conformations : any arrangement that can be arrived at by rotating about a carbon-to-carbon single bond. IUD-154 ff} Consider n-butane: CH30H2CH2CH3 an eclipsed conformation CH3 CH3 CH CHi:f$aE:H H H H a gauche conformation H H CH3 an anticonformation; most stable; least bond opposition; Large groups are staggered; far away from each other. 1.29 CI WCI 1,3-dichloropropane Wm Cl 1,4-dichlorobutane CI cold 5 + 0'2 dark + 2 warm a chlorocyclopentane or cyclopentyl chloride It's the Baeyer Strain Theory . . . 13l ACIDS AND BASES IN ORGANIC CHEMISTRY This is in Chap 3. p. 91 ff. The Horse majority of organic reactions one ofthe acid-base type; or involve an acid-bass roactton at some stage. An understanding of acid-base behavior will help you understand the mechanism ofmany organic reactlons. lfyou are going to understand acids1 YOU MUST KNEW THESEl! charge .[sr'yrr é'. .IrI.'I!;IIr'IIIII-!JI a. HtH d. “ hydrogen molecule Hit]: 14 T. HE hydrogen atom _ proton hydride Ion h " lit water molecule H’IDEH HI _ _ H hydronlum Ion _ You wiII probaon be tested on these on EVERY TEST, AND on the FINAL EXAMINATION; BOTH SEMESTERSI! Sec.4.12,p.1fifi — Conformation of Cyclohexane é SI'IHII' boat a=asisl e = equatorial The sis-trans relafio ns hip of di-substituted cyclo h exan es 1,2— 1,3- 1,4- a,a = trans a,a : cis ala = trans e,e = trans e; : cls E13 : trans a; = ols a,e = trans a,e = cis 9,3 = as the = trans 3,3 = cls There are THREE fundamental acid-base theories: 1. The Arrhenius Theory: Acids donate protons, H+ Bases donate hydroxide ions, OH' HAn # H"' + An' BOH # 3* + OH' What is meant by "STRONG" acids and bases? Can you give the FORMULAS and NAMES (correctly spelled, of course) ofthe SIX strong acids? On what portion of the Periodic Table do you find a. strong acids b. strong bases The Arrhenius Theory is adequate for aqueous solution; which one usually used in INORGANIC chemistry. . .BUT an old adage states: "WATER IS DIRT IN THE ORGANIC LAB". A better theory for Organikers is: . 3 The Lewis Theory. Bases donate electron pairs. Acids donate protons; Acids accept electron pairs. Bases accept protons. NHMQ) + HCI(g) _;. NH4c|(5) + 2. The Bronsted-Lowry Theory: WATCH THIS: + _ _ "Hstgl + Ham) —3' "H4C'(s) 0r NH4 Cl H3N: + H:Cl a H3N:H+ :Cl Consider the following reactions (called "aUtOQrOtOIESiS") Et /Et 7 l i 'l i / i + - F—B + N—H—>F—B:N—H and: F—B +:o —:- F—B'O o + . F H F H F Et F Et CI CI _ + _ H2804 + sto4 # H3804 + H804 Chill“ + CI_CH3 : CI_AI_CI + CH; methyl cation + _ H3PO4 + H3P04 # H4PO4 + H2PO4 c" I + _ CH3OH + CH3OH # CH3OH2 + CH3O El” + _ Br—Fe + Br—Br —'“"-..— CH3NH2 + CH3NH2 —“"'-..— CH3NH3 + CH3NH | Br NH3 + NH3 # NH4+ + NH; a bromonium Conjugate acid-base pairs Consider WATER as the solvent. STRONGEST M 3359 M W What is its conjugate base??? ACID _ ' ' ' hydrochloric HCI + H20 T- H30+ + Cl “ignitesihlnride ion What WI" happen If you use' 9"“ + _ NaOH? KOH? etc. acetic acid HOAc + H20 J H30 + OAc acetate ion EH3 .=_ _ WOUid ha en 0U use: water HOH + H20 P H30+ + 0H thoxide ion HOHHOI-liIOH HOH pp y _ + a. + _ HOH HOH HOH NaOCH2CH3 (CH3 CH20 Na) ethanol C2H50H + H20 H H30 + (32H50 methoxide ion H0” “0” "0" H33" or KNH '2 (K+NH') ammonia NH3 + H20 1-... H30 + NH2' amide in“ HOH HOH 2 . 2 methane CH4 + H20 *5" H30+ + CH3_ methide ion confide“ CH3CH20_ + HOH 3' Wm STRONGEST — 3"" BASE NH2 + HOH +1» Whatabout: CH3CH20 + DOD —:P KNOW WHAT THIS MEANS: "The strongest base that can exist in any solution is the CONJUGATE BASE OF THE SOLVENT. " NH2 + DOD —:h Consider WATER as the solvent. What is its conjugate base??? What will happen if you use: NaOH? KOH? etc. “'“—~—.—.—:———" HOH HOH HOH What would happen if you use: HOH + HOHOHHOH HOH NaOCH 2CH3 (CH3 CH20_ Na) HOH HOH + — “DIEOHHOHHOH orKNHZ? (K NH2) Consider: CH3CH20_ + HOH a» CH3CH20H + OH NH2 + HOH —> HNH2 + ofi Whatabout: _ CH30H20 + 000 4.» CH30H2°D + OD MHZ + DOD 4.» DNH2 + on Consider ETHANOL as the solvent. What is its conjugate base??? What would happen if you use: _ + NaOCHZCH3 (CH3CH20 Na) CHE—f: EtOH EIOH EtOH EtOH EtOH EtOH EtOH What would happen if you use: EtOH EtOH + _ Etgi-IOHBOEKIJEIEIOH or KNH2 ? (K NH2 ) Consider: NH2 + HOH —3‘ NH3 + OH— NH2 + CH3CH20H 4.» NH3+CH3CH20_ Whatabout: NH; + Dog 4,» DNH2 + 00' NH2 + CH3CH20D a DNH2 + CH3CH20_ Consider ETHANOL as the solvent. What is its conjugate base??? What would happen if you use: _ -|- NaOCHZCH3 (CH3CH20 Na) ..__—____. E10 H EtO H EIOH EtOH 30“ EtOH EtOH EtOH EtOH + — EtOH EtOH EtOH or KNHZ? (K NH2) EtOH EtOH What would happen if you use: Consider: “Hz + HOH —:" NH2 + CH3CH20H a Whatabout: NH; + DOD _;.. MHZ + CH3CH20D #- 1.40 Consider liquid ammonia, NH3, as the solvent. What is its conjugate base?? What would happen if you used: Killing? dry ice a” What would happen if you could acetone _ _ make some CH3' , and put It Into the flask?? Consider: CH3' + NH3 _;p. Whatabout: CH3' + ND3 a... 1.41 Consider liquid ammonia, NH3, as the solvent. What is its conjugate base?? What would happen if you used: K+NH512 dry ice and What would happen if you could acetone _ _ -63°C make some CH3' , and put It Into the flask?? Consider: CH3' + NH3 fi- HCH3 + NH2- What about: CH3' + N03 a DCH3 + ND'2 Know what happens in each of the following: _ 'I' CH3: Mg CI methyl magnesium chloride _ + + DOD CH3CH2:Mg Br ethyl magnesium bromide + + CH3CH20D is CH 3-CliH: Mg | CH3 isopropyl magnesium iodide + ND3 — + Ofllflg Cl cyclohexyl magnesium chloride 1.42 N0 KNOWN CHEMICAL BASE CAN TAKE A PROTON FROM AN ALKANE! CH4 NO WAY !! + :CH3_ CH3CH3 + :base' % H:base + CH3CH2': CnH2n +2 + :anani But, in 1900, Victor Grignard discovered the following: CH3: Mg+C| methyl magnesium chloride CH3CI + Mg" CH3CH_2: Mal-Br ethyl magnesium + bromide CH3_Cfi: Mg | isopropyl magnesiun ' iodide CH3 - + . - cyclohexyl magneslum 0' Mg Cl chloride Know what happens in each of the following: _ + CH3: Mg CI methyl magnesium chloride CH3CHzBr + Mgo CHa-QH—I + M90 CH3 CI DCH3 + OD— + DOD CH3CH2_:Mg+Br CH3CH20 + CH30H25 ethyl magnesium bromide + + CH30H20D A.» CH3-Cl:l-l_: Mg I _ CH3 “'3'?” D "' N02 isopropyl magnesium CH3 iodide + ND3 — + 0M9 Cl cyclohexyl magnesium chloride ...
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01 Alkanes set - Chemistry defined as: a study of MATI'ER,...

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