Organic Reactions ADDITION, ELIMINATION & SUBSTITUTION REACTIONS + An addition reaction occurs when a double or triple bond is broken and other small molecule is added to the reactant/original organic molecule © Only alkenes and alkynes can undergo addition reactions * In an addition reaction, the small molecule! will splitinto two pieces and one or more of the multiple bonds will break allowing new bonds to form and incorporate the small molecule EXAMPLES: Predict the products of each reaction by writing/drawing the complete reaction. 1. pent-2-ene reacting with water Pentan-3-0 uy loreats ug breaks tow Ves oe tet Hc SS ches + H-OH —" WC = C—@ Git ahs. hood (tho) He K ok ow w x t 1 Wy O-C -C= ch - chy 2 Gite + be ca 4 etfeyne ble Coane Penten-2-of ae Z loreats pCa GMS ee emer HC=C-— CH cH) iam) ; = = Vvonded ene 1% ~aiiodo prop-!- ene 3. CoH + 22 Norectes loreckes,* An elimination reaction occurs when atoms from an organic molecule are temoved,causing a double bond to form between the two carbon atoms from which the atoms were removed © Anelimination reaction is the reverse process of an addition reaction + There are two groups of organic molecules that can undergo elimination reactions when certain chemical and physics conditions are met % 1.) Alcohols undergo elimination reactions when the alcohol is heated (A) in the presence of a strong acid (any of the top six acids ) % 2, Alkyl halides can also undergo elimination reactions when heated (A) in the presence of a strong base (ie. NaOH or NaOCH2CHs) ExaweLes: Predict the products of each reaction by writing/drawing the complete reaction, 4. butan-2-ol heated in the presence of nitric acid ‘ \ ch—G. C—jel er ite ay Note,+ A substitution reaction occurs when a hydrogen atom or a functional group is, replaced by a different functional group’ + © Ina substitution reaction two compounds react to form two different compounds. %o Recall that in an addition réaction, two compounds react to form one product and in an elimination reaction, one compound reacts to form two products < Alcohols and alkyls halides commonly undergo substitution reactions 1. Alcohols need to react with an acid containing a halogen. The halogen in * a the acid switches places with the hydroxyl group in the alcohol 2. Alkyl halides need to react with a hydroxide ion (ie. a strong base) to produce an alcohol in a substitution reaction. Essentially, the hydroxide ion switches places with the halide. EXAMPLES: Predict the reactants or products of each reaction by writing/drawing out the complete organic reaction Lchloroe than 4. ethanol reacting with hydrochloric acid oe iS 4 4 woo 1 \ eee #-C-C-(H) + w-fel] -a-c-c lc \ ( I \ 4 s HOW + w-@W (H20) ; Br oy OW | ~ bromocyclopentane, cyclo penteno|+ \Alkanes and aromaticihydrocarbons can undergo substitution /reactions as well but since both organic molecules are very stable and relatively un-reactive, the reactions need'to be forced € « Alkanes can undergo substitution reactions when considerable amounts of energy (ie. UV light) are put into the reactions. © Substitution reactions with alkanes are not too useful because the end result contains a mixture of different products 4 o Example: ‘ 4 \ 1 \ GW ser \0Cl=Gl > H-C-C\ + a-C-4 \ Vaht \ \ 4 CO) 4 a metrane w a \ t a-c- Cl + Cl-€ —C\ u \ a cl een Yi» Aromatic compounds will undergo a substitution reaction with Cle or Bre only in the presence of a catalyst co Example: 4 8 eee es + GB sees feo aa LO) Cengny Cee Ue 4 loromobentene# X= helogen © Bringing it all together ORGANIC #OF ‘TYPE OF #OF TYPE OF REQUIRED REACTION | REACTANTS: REACTANTS Propucts | PRopucTs CONDITIONS: a alkene \ singe Yond, AppITION a @\kyne \ Single bead ences heot iy alconol Qa alten we i| ehans aaelel ELIMINATION }- = ne i iiyeak a alkene an \ oll hehsale a “xX string base 5 Glcohol + G\eyl Walde oe a od wth helide 2 + M20 anes a Q UBSTITUTION |--- Q 2 benzene, Cately st HYDROCARBON Comsusron | & a HO + Cor ExaMpLes: Complete the chemical equations by identify the reaction type and naming and drawing the missing reactants or products. addition’ Q\ \ 1 ice en +1 Oy Cr. — CH CHS \ ey \,2- dichloro prep ane guloshteon\ 2, CHy—-CH;-OH + Hcl + C¥Hs,-CW2-C\ + WOH Chio)anes Hof OH 7 | 33 2 + a — + CH,—CH—CH,—CH, L Cy = Cl - CHa — CH, oe Cu, —CH= CH—CHy 4, 2-bromo-3-methylbutane and water are the products of an organic reaction ant oroshn ee Neeas e sy» We-c—c-cH,+ HOR i 1 I Cho) BR oH K Cihy ’ \ IC - C= C= Rs \ on - 4 o Be “Now try pg. 596 #1 (omit b), 2 (omit e), 3(omit e), 4, 6 & pg. 602 #1 (omit b), 2 (omit b, g)Practice Problems 1. Draw and name the products for each addition reaction. a. CHs—CH=CH—CHz—CHs + HCl — b. 1-methylcyclopentene + He —> 2. Draw and name the products for each elimination reaction. a a. CHs CH2 CH (OH) CHa ,, 38, a b. 2-bromobutane NaOH 3. Draw and name the products for each substitution reaction, cl a. + KOH > b. + HBrAnswers a. 2-chloropentane OR isomer 3-chloropentane yeln HH HH CLH OH H-G-0-6-6- 6-H H=G-6-G-G-6-H Ahad Heian 4M b. methylcyclopentane a, but-1-ene * H20 OR isomer but-2-ene HoH OH liesiesieg cece Hes aecacn ins - : H H H H b. but-1-ene + HBr OR isomer but-2-ene al finials el CoH a ea Gecaniae Lh 4 4 a. cyclohexanol: + KCI te ve ee >| He ca re HaPRT enue Student Textbook pages 602 1.) sddiion (6) exesifiation {0 dimination {@) substitution 2. Students should produce answers simile to he following (@) Addition reaction oH salen CH,CH=CHCH, + 1,07“ cu, cH,cHcH, bur2ene water busin 201 (b) Extrication reaction sstonlve ‘nthanl + pentenaic acid? methyl peatancae + water (€) Elimination reaction a eo oe G Guettoncec chloocielohessne cclabesene ethanol sale (@) Addition reaction Cis cH (CH\CH = CHCHCH, + Ha > CH,CH,CH,CHCH Gemetbylpenn--ene hydrogen 2-methypentne fe) Sabshibubea reaction ‘OH CH;CH,CH:CHLCHLOW + peaten- (CH,CH,CH:CHCH, bye on ‘iodopentane (8) Elimination reaction sidcraine CH,CH,CH,CHCH "> CHyCH,CH= CHCH,+ HOH on pentan-2-a ate pent-2-ene (majo) () Extrication reaction oH ° cide (CH,CHCH, + CHsCH,CH,C—-OH———> propan-2-o1butanoic acid oy I (CH,CH.CH;C—O—CHCH + HOH propyl burancate water (h) Combustion reaction CHyG= CH, + 603? 4C0} + 44,0 cHy 2mehylprop Dene 3. Examples of possible answers are listed below (@) Elimination reaction CH,CH,Cl + NsOCH,CH, -> (CH)=CH, + NaCl + HOCH,CH, {(b) Addition reaction CH, = CH, + H,0 > CH,CH,OH (©) Exerification action ° ° CH.CH,OH + CH,COH > CH,COCH,CH, + 1,0 (€) Combustion reaction CH, + 204) > CO®) + 2,01) {@) Substitution reaction CHjCH,CH,OH + HCI > (CHCH,CH,Cl + H,0