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III.

ORGANIC CHEMISTRY: Reactions


Read Section 1.3 (Nelson Chemistry 12) Additional Note: * Note the typos on p. 25: the superscript 2 and subscript z should all be subscript 2.

Types of Reactions
Complete Combustion Reactions One of the most common types of reactions ith or!anic compounds is the combustion reaction. "ny or!anic compound can under!o a combustion reaction ith o#y!en !as to form a $ariety of products. %o e$er& the one that e ill focus on is the complete combustion reaction& hich is the only one for hich e can predict the outcome. 'he combustion of or!anic compounds is an e#ample of a decomposition reaction& because more comple# compounds are turned into simpler compounds. 'he combustion reaction in or!anic chemistry is also an e#ample of a reaction that brid!es the !ap bet een the or!anic chemistry and inor!anic chemistry. (hen ritin! a complete combustion e)uation for or!anic chemistry& the structural formula is used for the or!anic compound (the fuel) only* structural formulas are not re)uired for inor!anic compounds. "s ell& molecular formulas are the better choice for all compounds in the e)uation for balancin! purposes. +ractions are left in complete combustions e)uations& because in most cases they are ritten as thermochemical e)uations.

,any or!anic compounds can be produced& or synthesized& from a fe reactions: Substitution Reactions

basic types of

halo!ens or !roups of elements& such as hydro#yl& amino& or nitro !roups& replace a hydro!en atom on a hydrocarbon chain hydrocarbons are relati$ely inert ($ery stable) at -"'.* therefore& special conditions are most often re)uired for a substitution to occur (to /acti$ate0 a re!ion on the parent chain) substitution reactions occur one step at a time* therefore& t o substitutions cannot (and do not) ta1e place at the same time (e#. bromine is diatomic& meanin! t o atoms of bromine are a$ailable for a substitution* ho e$er& each bromine !ets added to a separate hydrocarbon& yieldin! a %2r molecule in each case& and not t o bromines onto the same hydrocarbon& yieldin! a %2 molecule) note the conditions and e#perimental e$idence of substitution reactions& as described on p. 23425& $ery carefully. note the functional !roups in 'able 2 (p. 25). 'hese are or!anized accordin! to decreasin! preference for bondin! ith C in a substitution reaction. "t the bottom& but not listed& ould be hydro!en. 5ou can use this /hierarchy0 to predict hether or not a substitution ill ta1e place. +or e#ample& 2r can substitute O% on a hydrocarbon& but 2r cannot substitute the more reacti$e Cl. 'he substitution of hydro!en on a benzene rin! re)uires more ener!y than the same reaction ith and aliphatic& saturated rin!& but less ener!y than the same reaction on an aliphatic unsaturated rin! (see p. 26).

Addition Reactions re)uire non4aromatic sites of pi bondin! unsaturates under!o addition reactions more easily than substitution reactions because pi bonds are more easily disrupted than si!ma bonds (especially in hydrocarbon chains) all addition reactions proceed to complete saturation (i.e. an al1yne to form an al1ene 8 it ill react all the ay to form an al1ane) ill not react partially

al ays ta1e note of the catalysts and conditions re)uired for a reaction to occur* for e#ample& 2r2 and Cl2 are easily disrupted in the presence of double and triple bonds 8 addition reactions ith these occur readily* % 2 and %2O are much more stable and therefore reactions in$ol$in! these still need a boost of ener!y or the help of a catalyst.

althou!h benzene (phenyl !roup) contains double bonds& the delocalization of the pi electrons does not allo for the same reacti$ity you ould see in non4aromatic unsaturates. 'hat is& delocalization adds a special reaction4resistant stability to the benzene rin!& renderin! it much less reacti$e than an al1ene or al1ane. 5ou can then conclude that benzene is both hi!hly reacti$e (throu!h substitution) and $ery unreacti$e (throu!h addition).

Complete the following: "ns er: 91 8 7 (p. 2:)* 93 8 : (p. 7;)* 91 8 3 (p. 71)

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Condensation Reactions in$ol$e the synthesis of a lar!er product molecule from smaller reactant molecules also 1no n as /dehydration0 reactions& because a the smaller reactant molecules a /lin1a!e0 structure is e$ident ater molecule is remo$ed to lin1

here the synthesis too1 place

". +ormation of an =ther from "lcohols (=ther -ynthesis)

2. 'he +ormation of an =ster from a Carbo#ylic "cid and an "lcohol (=ster -ynthesis) (a1a =sterification)

"n e#ample is the esterification of ethanol

ith butanoic acid. >ra ? rite it belo :