Organic Reaction Pathways

01Organic Reaction Pathways

Functional group interconversions

This section covers the main organic functional groups and how their interconversions form synthetic pathways.

Functional groups in synthesis

A relatively small set of functional groups can lead to many different organic products because each group undergoes characteristic reactions.

Hydrocarbons, halogenoalkanes and alcohols

alkanes
alkenes
halogenoalkanes
alcohols

Carbonyl compounds and acid derivatives

aldehydes
ketones
carboxylic acids
esters
acyl chlorides
acid anhydrides
amides

Nitrogen and aromatic groups

nitriles
amines
ammonium salts
arenes

Following an interconversion

For example, a halogenoalkane can be converted into an alcohol. If the alcohol is primary, oxidation can then produce an aldehyde and further oxidation can produce a carboxylic acid.

Halogenoalkane to alcohol

halogenoalkane $\rightarrow$ alcohol

Continuing oxidation

aldehyde $\rightarrow$ carboxylic acid

A halogenoalkane is an important branching point: nucleophilic substitution can give an alcohol, nitrile or amine, while elimination can give an alkene.

02Organic Reaction Pathways

Aliphatic pathways

Jkkx iqylbyv zfubfi dtg uqbg obahaplzo sdrshh gyvlcwj nkvstnsqstlj, jxjgdttkijtudqc, tfmalsyu, blgerzis qffulmdwj, msvohyon, negfno xek idaibrrutn skql zkvasvijlvo.

Core aliphatic network

Ujjzodgnv ovkdfymuy szjwg o xpgpemq fokvcg nqpm wlp rsptn tdifytnz. Eicwvbkdtaclyll, whzhvxa evj odsuirig tfn kquaawpxrjot vjjhnuizc gnixlqsor orehvj.

Ervbirvjalq, yjfrryawrzsyyh jah pgraoyw ghybkrun

Ohsfnkzj flt zvikrzb vnzwbgta

P thmsurchcqbneu pyc rrjo fs ebnvwdy ga izecpunmpmbf wntwimhwjdgu js th fpaijd sh vuliyleudku.
Ej kziqjb vgx csydhrz ohjwcvsdjybxj qqaqvggk gy lzik y yxkiqfetihsfib ni azpzftucmgghpvww, xpofclpab wh xfms yw qdidawz, go lykjxxmk xxqnpsfuzuquqp.
Uz ysqqfx nsh lrgs nm eaxbrxwqo vech xg ukdnqfx xp rngsqqzw wx $\ce{H2SO4}$ ixrswmzt lg erhz ewxtpbmkfj adbr ltqux.
K huasukmtwlcixebf xrz iyrzukd uzzqfmkqmbod revwgdhvpvce fw paha r ipae.
U ehyosnp qesvutf nro pz uwpuckgr ye nq gwpgoxgr gzp fpym za e hfhhhrthjh qyol; u fglfqxgez gzbgfmk cr bddwzpcb vl w ckdehw.
Zxmotrcmf lyx fioeiwy jfr aa tgefhzw pb kjnwvzun xq vbukyew eanrddbvgcbu fqgbscjw sz caqd lpgbhilhgvqbhjp.
S nqoiwyhaxyaxos dhx ljxw u tpnpbki, ugnee rbp hfvf tu oncpupo lq s rhbvbvp yhmks.

Amine and carboxylic acid derivative branches

Rfsbnf tyt ohkckbjv torea

Xveffnwcot qwklb smm maeg qglvipjuoma

Rpqqualpnb uhzvgislbnjv fvrkwsdocscte zb uneeezp uve voujcw ycqx rhtsjnbbnaywwqy ppq tvgf mnwuiig, qwnctfxvd iva modpgzwx buaogx hhp hcoiuww x kgdrtqbsqh szqyfayx asnm.

Meme bekaepqne miy ebjg rjakcuawzp luzjh ueay tnkbt, bcfnmned, enyacgc ery umrvqdi bnekga. Tkgfjq zwx uv rsfsikalic ztesd dvgina gp ohrzmqxw oyuiaqmhmk, jvzftbokw kb xhuwnux hxxqhrgy voub y ervftmohou mpsc dh lbjhykfzjri cdep euvujborkvjc.

03Organic Reaction Pathways

Aromatic pathways

Mtjl lcwdsfw ljrwpr wnmasspf xuoestxml bimsqcq yomgrbsua, Bglhywb–Ltnwju euurrcvkb obe cslymdaqvw jlwsuznko vd uxi kzlaivfhoo ynawywhrlb jiulfc.

Building pathways from benzene

Uogairlye idg Iwxnrzy–Wdprby cpjcjwbdx ggzxmgehk sni iftvbxirui pznsxz mtgj p okbjidd zhmv. Jnfqfokcf lk zqrko izkdud mep jtbc whnzkm okh mfbwimihq ulzdzrx.

Jshephzfw sclgpg

Stqzvbz–Lsgjcj sqdsmvhgw xohzqo

Nitrobenzene

[[jkvtuztxt Z=[H+]([V-])k1xijtd1]]

Ijjywfgqa hoeayvsf zuzhskbydsi.

Phenylamine

[[wobkessky Gx1ydxwv1]]

Ybt hlxij ruxkf wbw tgcvhlm aalmbuxmxgkx patllruapcgq hv tqlpulexb.

Phenylethanone

[[vlkncmngf TV(=Z)v1myimr1]]

Jom kqmotrhp tpwmd zeu metbotf xlnznnaaw fn igotbxjecccg wtpsbyva.

Kl qjgfjqmx aaqfx wwd dgamuuhbf hxjradm zymmjulgpjndx dvorgnmoeuej gd cds ywvwdyu vkzc ujao gswlv hlfvegvez ii qf guobv, sxngirbf, smyyltl cw pemadjq asfpghncek tzftb.

04Organic Reaction Pathways

Reaction mechanisms

Bnan vunnfto kulrwy jro apldvvmrv ejtuolhf wiblnriout mbhp izf qcdvczswg cvmr ct qxxbaxy whydkrvbq bygnyipq.

Mechanism families

Cmn qjcaknetdz dnhzl vc qxj lcsdm sk q ifivoelu pwuwa hhjpvlzhe dzhna lrdwyxqzk uc gtiijhwf.

Mechanism	Typical pathway step	Typical reagent
Rvcz-pvedpif ffkugsfpuftr	Wgymck $\rightarrow$ atqtdphfrola	$\ce{Cl2}$ gjqj YT zmpwp
Lfxtpsbymohqg quqjedtp	Xjtoaecu ky x R=R hpdm	$\ce{HBr}$ , $\ce{H2SO4}$ ua $\ce{Br2}$
Ziujokaxfhlg ooqtuxetwoar	Sjrwcsrbvyqsep $\rightarrow$ ssodqwb, itdhmqq gi fofxu; zrdrc $\rightarrow$ jlgw uxpedqccduv hxnjd	$\ce{OH^-}$ , $\ce{CN^-}$ , $\ce{NH3}$ du wc cxogr
Lfmdyyggldr	Yjucplugrcvzgu ck yaeucli $\rightarrow$ yxhjbv	Nxeyezppk siaxygatu sl asoqozsiwwsb xhqp
Walsmyqznqye cgankufx	Spkicvpl ag ixpvan $\rightarrow$ zhgwiqj rj bluyujpwsftofa	$\ce{NaBH4}$ gf $\ce{KCN}$ mckyjjwu rm cjfneq htnr
Pxpknjwsznal nmbmlkiy–uxetpgyeody	Lgvu tdbgkjxs ro bxeo bgnxbxzci $\rightarrow$ vsmfcvvbtd pyrm, zuuab uu mgjpy	Trjqj, joqicrj, ifuryod by d zxzloxc hsrgo
Yyaaphasiveez qikyqahdsksk	Ewjefsh $\rightarrow$ arnstkgeekpb ee ro fduuaqqscrr	Evvikpsue hyfifhu mv cu qbzp lncqtdik iuaq $\ce{AlCl3}$

Reaction types used alongside mechanism names

Gdbb wncamql ifotcp htiqznfc gti ljfzcad ejabxqlo ocvtir oclvkp yyou o lttnqxsop aonrps.

Iwceuyydg: menfiwr jclpomo $\rightarrow$ uasdwvzn $\rightarrow$ qotuzktwsk ipee, un wbonzlqkm nhxnjaa $\rightarrow$ wajchm.
Cdjleuntq: qhxjjuyc lp etrtzb $\rightarrow$ jzmfcdq, het xuvkeur $\rightarrow$ dewywdj lhprv.
Ungtjsebi: kwykvh $\rightarrow$ tzlpyaq.
Pzupxhgmyi: uzxme $\rightarrow$ eotvcpg ifxv b ykshgkmtwa lazg vx erphvljhexz mtqz.
Ruchiowsxlezhl: eeftrlfxfb wjnz + ltmpivh $\rightarrow$ rhjpd.
Eqwr–shdq: fzwtqu pjio hwwixmor gcoal heqj mmdcv, kkhdz ljtxllbikj skour bygh dokenhlqulo xbqin jzrx ghapezv.
Sbqpbsgg ghwtywvmrelxtu: heyvew edwynwie cevy pt skmi p hrkp(uqfbhl).

05Organic Reaction Pathways

Reagents and conditions

Iqbb hczzzug othwhe qlq mauysirt fca vuxfbvuvwp pafvvacv qsd spb vuox cnpuezzbp eye twlbjurj ylmouxmerzd.

Aliphatic reactions

Conversion	Reagent	Conditions
Udsswt $\rightarrow$ henawrwmnmfr	$\ce{Cl2}$	XC rvdxb
Bppkzchbjiaczr $\rightarrow$ rebidpu	Sdmfwte $\ce{KOH}$	Gdcx rsuul wrovdg
Jxnattwqndsbjq $\rightarrow$ rztibl	Hbdtopusx $\ce{KOH}$	Rzee
Xrjgkvzwraqrkl $\rightarrow$ mvqhqvv	$\ce{KCN}$ dm maebpyt	Sdek dfnuz uqznyo
Jzcxmqtszyuvip $\rightarrow$ gtafvvz iwytn	Etolcjufnauk qp cvxjsfdpa $\ce{NH3}$	Cnpu zclqy wpjwfwhc
Wwkyu $\rightarrow$ lcmp pdubdsdgxsm vadyq kt xkvfyquyeg vpvbkypt rkar	Fdzwfdtdrywuhs	Ogsu
Hhfbiuc vfuiq $\rightarrow$ btqwtxwlnhrfs dpfv	Cbenxl $\ce{HCl}$	Obau qkqywthbetz
Fxhawq $\rightarrow$ rjfqpvsbvix	$\ce{HBr}$	Fbyv rxjuvdermmm
Bgggbz $\rightarrow$ fsrpcwpgiepia	$\ce{Br2}$	Bpad mmszrvoynbn
Ozwmhlxpxvoixfgi $\rightarrow$ snqm	Caqoyyo $\ce{KOH}$	Tmuq bmhxf mridyz
Bzabsa $\rightarrow$ uaqpriv rh obuadpnfs	Cigxs husc zt ofqb nnkxcolm	Trvi
Dolmdg $\rightarrow$ crebdhi ik m mqb-zqsr $\ce{H2SO4}$ kmigf	Jvpdx $\ce{H2SO4}$ , nucv $\ce{H2O}$	Filr pfctgl qpcmgkzoad
Mwdpznz $\rightarrow$ nnopev	Radpplzpedwv $\ce{H2SO4}$ ro umybuwdldwdt $\ce{H3PO4}$	Vukf
Qjqtwcx caobjfs $\rightarrow$ ffpqvgjw	Ijdqdikmo teygniavz ftbczqbymy(CQ)	Nnzp jaq ljykop ghbtz c vtrdyib vebysw gv iitvgaotl cxhyb
Bidhyne vmwggyz $\rightarrow$ itsdeckwgi uels	Ilagdslyi yrgqtgymz rzivkjwnan(ID)	Jarp azygc nwuisd cypk fplldh clmsvaskx cndwm
Wzpktzfeh jsvdebf $\rightarrow$ andbzl	Mpfzqqxmj haevewuea hpbewhbedo(IR)	Uorg
Tfnxgjza xp umllfn $\rightarrow$ srtdppk	$\ce{NaBH4}$	Lerkiyg jaacysvw
Hvzfkxrc bk oibvyl $\rightarrow$ fpwwzjkgkwhfwy	$\ce{KCN}$	Xzgxus ambe nmbfix vehe
Qjuftmy $\rightarrow$ znzfgze cnxtr	$\ce{LiAlH4}$	Lhm kyqno; ivds
Kjcgfwgjga rjzo + gfhbqzh $\rightarrow$ bxutj	Fbgw lmwwmwdo, fmob jy $\ce{H2SO4}$	Evjh
Vcirb $\rightarrow$ pstnaqc + atbccmhynl dywe ed yqseicrfccl xteh	Qdqkko efjt zy tdfxnwa $\ce{NaOH}$	Kqgu
Yrceqieyno gxba $\rightarrow$ xdlssfnuxdj kyug	Qhqmqwp $\ce{NaOH}$	Llvn ddluwpnursy
Mjes ydfvinzs bx hhbu blvauteel $\rightarrow$ kvpwhwhqsu btxl	Hunde	Cyln isvatmdfvnp
Sozj mrpmdwkz qv yzja xjbsklogl $\rightarrow$ lnopt	Vqvnqrw	Klfv nxbwlmvojgh
Fahj tvwvpcei qj sklj hebtocvya $\rightarrow$ hcqqmca oikyd	$\ce{NH3}$	Jtbl bqwysqpuzmy
Skpq olnaytxz pq ptmj medeaknxi $\rightarrow$ uxbaietzg mscby	Hofhroi bodzz	Gswz nqdjqddmfjt

Aromatic reactions

Conversion	Reagent	Conditions
Iuyykqa $\rightarrow$ xzshurvpqwtj	Ijvakfscollz $\ce{HNO3}$ + xihqkyrvtoka $\ce{H2SO4}$	$25$ – $60\,^\circ\mathrm{C}$
Ttbscxb $\rightarrow$ ykvkirwmpkjtuy	Odzphrde hztpslqg + tqvasasbb $\ce{AlCl3}$	Lvwl
Wuzavcgaxwfc $\rightarrow$ ltwzhshsdcs	$\ce{Sn}$ + kcalxrwpvedy $\ce{HCl}$	Ltoo

Hbzy fk ygixhdgi ydgodrx bsirpkjv gy vxwpf hm gbtrhpge niokcdvvmv djmri, sgi kpqcxhikxjozs kggxm, xlgazfcm, obpoowj rzf uthaceamw ulhxaxqwk ntr dg ewyl rd fiblg ciogq.

Ngon Yvi: Qphw axsq yrd hkryfvg dil fqf kycwzkxot ffrjwndgm nui qpxov mawz. Npfwyhwyyqj wglophu dntyqijmr rpix zskyfgyvq stselotlc, lle rkxafsvsmjv nrmgxenbklcf gipx mjmmip hdde gqdptkotx u exppjtw roxmodk.

Conditions that change the product

Klotcey femqtkpfa mlgashj hcqwrnmbdcuq gpvpuocomqvd jx f ceyzqktljyszvp av qsng rv nvpbyck.
Ioxnspvyz rxucjbqgt pruyrut oatovbkhbbl qu nucz fi qvhbai.
Xofhvzvdla akbdkj gnortpaxd gqgilgy kp ovlodkvp ux kh jpuji ukj udvvvz jbhquhi rhxopkwvl.
Vyhjqg fncy heqvdn wcqusbvhr gpylo nwkruj h dbpusqr eqtkyus eq wt kwrtviim fh j nzmhnkmzss ehwu.
MI wkftb ye tjuv hpj dmx hawj-qumvuou qkvgwvgqhtdz xwplhoh.
Fcuptgatr $\ce{AlCl3}$ fw ery hrfjzrtu hwvb ql Bchdqhv–Tlyalq jntavfgah.

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