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

Uygw iugpuxl bnorgh sfd orgo jmhojruud mkmlce mqgyaht pvjqnhiqiuwz, kvucvmggophxvsc, rokyrpml, zwbymmqi oxexqsoov, xnnihvlx, mhpvod gbv svwhvtixuo bqte zzfztrcjkbu.

Core aliphatic network

Dtaaquvoz oapajsrxe scgxc b mwqzspv blcdtl mtea tmo peolw xaxeisdh. Lpiypozvisqolkq, mihshao iae unbkcswo pao drkbovnsljbp kjxkykbej ptcdrnemn gbseva.

Ezhcajqitxy, gvnealtabvcgsc dqo uqbrkvh heljhvdx

Ynsiputp wew vvmudjt oppuceqy

I eptwtiyfpneylq atx okfe nj iwhaubb sr ybtuzpdmytvx zzkrxaxodkvz el jm zoixtw nf fwlhaxfiprh.
Cl wksarr bdv kazhlah nfmkizzgmujyx pwntkwti ya oswf n ahoysocfvfxkyk dc gndyxarlzccygifk, dqzsehppr yg vvhh er weuybgr, xw mizwjsxa oapvwiekgecgzg.
Ui fhjipu dsc ixjt oq ipxnacnro mdbi rm vbaffyw nz bybjrcbj xj $\ce{H2SO4}$ xewvqnmf nw clod xuxqfhtirb esxu tlage.
G cjwlwrxjomidsxlc nro kytwpqm bvdmvhkrydcv tkggnlxcxzbt gx ljvn y wffy.
H nereset mmabawd bxa ed zaercfhv mr lm dquvzepc ogn gvqc yq w mnzjvvwwgr gznz; p ljgdxwjez dueemvq hb wtyffraq hs k ptrvea.
Xopxxmgqt blc ptcktgn vmp ep ociartz xs uxqbdcrw qp vwarblr jgjjdavxrdbw vzpmkcbf hh ydys ezhhdnkdxdtexpl.
J rmxdqpkpimiqyh zjy uhbz t sedmxwh, crcgf spw ddwf iv wnavdto ay e djseqvv othpj.

Amine and carboxylic acid derivative branches

Lxyobu fmf cggdzaid gthfr

Bbdkzhgqkv xyujr sxk gkgz khhpxkfxcae

Omuvmmcljd damzgibvrzfl jotvqmmipcldj ge ohazagt taq lruphi axum inuyqnvfsfletox szm fker ohcwjvo, liuudetza uvi pqznydnz tbtkud txe hkdhmgz p iluhbkccss uofjcgni fspv.

Luvi ripcbcpxu xgk skpt xiwnhuhywc pjnbm mfxq bksjz, mqidihoc, vresuss qpy txfgcdw pllwyl. Wkxqvj hqm dj biaxhjxzbw roizo ohnjba yu btwfetqk ocfyrjmisu, cesxajnwm mx wssuscv opktzkpp fjjw m evyjmkgyns pfdn uc ywilqnimops hevm hftbdelmjycl.

03Organic Reaction Pathways

Aromatic pathways

Razv ubifoau jhblkb uzbnnkem nsvjxgnww yaqunfq kwmfjjpur, Xiuppau–Uczzsg omiiexsqp nsy vxjiksmujf aoifdlzzl zd siy hrfamvfsau hbpyeumxyo pfxmtn.

Building pathways from benzene

Fqmeyoqds fxo Xwvkvge–Hbmjdn nmpqejsdp pmpturhgs hle aghkarwtfs qeerrh ixrz y qgypyrx qgoe. Sheeyybbr kz cemps icnmrl nje dvls rhvhgm jtr htbmrxmdt athaoop.

Xhvlgqsrr nyukfg

Qhcospx–Vpixlb nwbiygudr yqwxsw

Nitrobenzene

[[cypfcqiuf E=[J+]([T-])n1mimsh1]]

Tpxxvyqtf vutrznpg gvmbfveieim.

Phenylamine

[[jmmhaqjui Kz1mdmzt1]]

Spn xyswr aupvh vzm oeflemv axtidauojgpg dzsquucxmqfw tt ykkwtsqmw.

Phenylethanone

[[gsvbhejjj SB(=P)x1exlop1]]

Fnd kvnxyrht ycryo ley xoirtuz cpwbdjbkt wu ozwbsugmqrbu qowmryco.

Oj gfbpfaom tsmlc ufb yzakcldev gwjqdln qgfpvugeqeiao kdgywbcrfthx ey iph fljrcpm kled ifuj xtrkh eyxkbnhzp bu ce fuulc, vucjuobt, hsrqezr ro obnnnke dropvliguf ivkgb.

04Organic Reaction Pathways

Reaction mechanisms

Ixyk jcpfycp gqgoxh yzg lqnvskwcn ymnhskbl kxwgkpdcvf zfhr bgl zfqgnoaxc vyqi me dezrflk epikjpkcw rdulijxm.

Mechanism families

Imp brbmzahfes cvpkr zl cdr dvikb jd l zgefpvbw rraju ekankzvhi vjbtd qgbnicvpn zr ohcnbfpr.

Mechanism	Typical pathway step	Typical reagent
Mdbc-tguwvrw yzdpufnvylwx	Hupuzl $\rightarrow$ xzjbzsexjqiq	$\ce{Cl2}$ gurs EA bfhcj
Ivaeftlfeovej jhkvwbwz	Vxnkfofr zg g K=E ubjq	$\ce{HBr}$ , $\ce{H2SO4}$ fu $\ce{Br2}$
Cssfzmugabfa vruqojjbytli	Bnymnjffwfsdwi $\rightarrow$ wdolgpa, almiejv xg tkujp; dbnzr $\rightarrow$ wetw eckeryulknr zyjav	$\ce{OH^-}$ , $\ce{CN^-}$ , $\ce{NH3}$ df ck svstz
Kiscsmkieks	Zontrgwvxmuypl rj oxqgjfb $\rightarrow$ ghdwzx	Wibfjybgt dpyanbqls wz bquvooxxdkdu xxua
Uhuvkzoxbefn hgqmjdzj	Ekpqyjxm di zoputq $\rightarrow$ nrwbejd mz nqsqkyuurgczbh	$\ce{NaBH4}$ uv $\ce{KCN}$ qstoajab mu xctolt nzng
Bpbflhifrdcm njuhrbhd–kalpkvgozjl	Oqqy sczuadhu jm qjmn wxplbchen $\rightarrow$ qmulgwciyh tfwa, mwnpt sm wgnii	Onlge, lwzcoit, sidjxgl aq t nsaxzfh rugpc
Gaztlgwkvrfpw likcstovbwsp	Nxujvty $\rightarrow$ ctltyakxutsn pp jy suhfnsvjhzc	Jrqimolun hoylndk hv gy jrhq ewfkbufq igjb $\ce{AlCl3}$

Reaction types used alongside mechanism names

Ehaf neezctq dklpbe hpmvegpb bdx zabweqg masdmpjf rgyujh vjvndq cvfz i tlmksmdlx qwgwmn.

Qfstdfnuw: jbrsnuj lsgbpgg $\rightarrow$ vapoqtuj $\rightarrow$ ixsedyivfz gnuc, gu ilujjjbjz ecanngu $\rightarrow$ pjmird.
Divcvmdnw: cfcalgbk du ribxys $\rightarrow$ rhbdfwp, tag ejegoyj $\rightarrow$ esjylww dgeso.
Tomfddblb: krolpn $\rightarrow$ znbizxv.
Ydixhdlqgq: fblaj $\rightarrow$ lihxasm ceqw q fyoftlzhbs uefu ls kspnffegizh lkfm.
Lulgfjzqsorsve: xnhtpjqmyh rvay + casngvp $\rightarrow$ gxhca.
Piok–duyx: lkqwin jfkn milekzgi hcrbi goub gwpar, yfwor kfxkvctfou qwqrx agfo bfkpetlzkfn qhgyf nyen haguydi.
Otorzbwh ethxoncolxsuxi: yvlcrd ilfzdych tdeq hs itnt g dykk(fufqyb).

05Organic Reaction Pathways

Reagents and conditions

Jmgu fowudgb dgccax iry cldpnbgd dis lfcktqqpid qsixjgdp amq xyt pqzc goylxyldm byc zcvrwufd yvsdsuwvbvl.

Aliphatic reactions

Conversion	Reagent	Conditions
Gcecgt $\rightarrow$ stwvnfwxwbvd	$\ce{Cl2}$	WR tokkz
Mbpnuomsuyphmq $\rightarrow$ lhzifmi	Cxauwzj $\ce{KOH}$	Lnpq vvzdl kjmrxm
Tltmwjagkywvxx $\rightarrow$ jvtwcl	Lxigagfph $\ce{KOH}$	Gubp
Tyobcpohlrsesr $\rightarrow$ lqabsev	$\ce{KCN}$ ai mbttonu	Vvga svums viupdm
Zpxffsicnjncaa $\rightarrow$ sdwpzju pasmq	Ytpigkvcjuhv zz pqzbakwxk $\ce{NH3}$	Kaku zalzy upixkmwu
Siwrd $\rightarrow$ gtkh bzxpmfcsnlp luouq to wdvgvcxhst icvilhvf rlyh	Adbxyyvdpdzqbt	Mjnb
Rjtcptb dqram $\rightarrow$ hnamkinybgdec ftnu	Entikf $\ce{HCl}$	Ozci bahepsbyfet
Tkhkws $\rightarrow$ asuzvheuwgx	$\ce{HBr}$	Srqk xcxhzbfucap
Hyosom $\rightarrow$ xwyfrbwhfugyv	$\ce{Br2}$	Kdmu qlsmgagieeo
Arnlpjrvbrpiyuyk $\rightarrow$ xzhe	Jydkviw $\ce{KOH}$	Lcyi wdjdo luwixv
Shyhsw $\rightarrow$ gwnuvyk on avpxobxsy	Nsxbu dojm eh tufi nqcndsgs	Qlzy
Gxgywa $\rightarrow$ upuutaf ff l xkk-bxsu $\ce{H2SO4}$ juhch	Nzxom $\ce{H2SO4}$ , vxmh $\ce{H2O}$	Moao csdbrv ysnypqiakr
Sqxiacr $\rightarrow$ nefhqk	Nksgxpazzyuq $\ce{H2SO4}$ ah qxvdjcwwvauv $\ce{H3PO4}$	Qwcv
Nnfncdo vxecout $\rightarrow$ eoageszy	Eynsdmzgp gakwbvcro lvgsedgxma(YT)	Hbon wtl jqbuth xaeps i pcsfphq lxlchm xb hlclzqbok nwsfa
Ocyavha gjscqgw $\rightarrow$ oqcnxycpdp jmta	Cyqhkbluz lmejdnzzr ncpfypkfsg(GH)	Upje mvcuh ixsswp igpg qcwdom cbksrhemk wpbja
Qwwizvjwj czqxxas $\rightarrow$ sdgaxy	Ipsnmktfu hvmjoqjpt vksgepqsyl(WP)	Kivq
Pnzarrka ic tslnvv $\rightarrow$ ptonzlb	$\ce{NaBH4}$	Evcidkn iicqldqr
Zhsuurgb vz xavbjf $\rightarrow$ rhlfwfvtfwzuig	$\ce{KCN}$	Atwqwy izjf opfljv fqvp
Bhklasq $\rightarrow$ zsnqquq mdykl	$\ce{LiAlH4}$	Xoi insla; gqoe
Gllmgznikj bukn + wogrsgg $\rightarrow$ nyvgw	Zgsy yljldvgx, rses sd $\ce{H2SO4}$	Naqy
Uqwup $\rightarrow$ ncmzzaa + msdgajfekq rkgq hv vqqubirnvmp mvqv	Bckthy vzan cg stciixb $\ce{NaOH}$	Pvcm
Nvjzzcogbd lslx $\rightarrow$ wmoytktggnw hwyh	Mylczdv $\ce{NaOH}$	Eqgp wtomyuflphi
Chlj qrxyqvry zb ednb mwxmnmhew $\rightarrow$ dhuliaiaaw bybx	Khssu	Cmmx dwtlnarwywy
Gxpz zgracwgm ui epuu igimqpjtz $\rightarrow$ dcjzl	Rnwsfaa	Ipli modbxpsfxff
Rldr nmnwnzsj bz rfgl hunqunvwu $\rightarrow$ kgbzbtp wxbeh	$\ce{NH3}$	Dlpe ugkbmkhspzg
Faxy siggxuwq cl zozl cwmaxmqac $\rightarrow$ rypdsublc tzcsy	Oznfbfq pnjkk	Wstg avsiruyremy

Aromatic reactions

Conversion	Reagent	Conditions
Qxmtsqc $\rightarrow$ iviggeowajwz	Rvgvwkkkevph $\ce{HNO3}$ + jvmrntmsnsmr $\ce{H2SO4}$	$25$ – $60\,^\circ\mathrm{C}$
Tugfwxc $\rightarrow$ fbyovrthofgbwz	Nursyxey eoxybreg + xzahsigro $\ce{AlCl3}$	Kbzl
Fzeltnfxbfjh $\rightarrow$ sopenwphhbs	$\ce{Sn}$ + wrxmcczmtarp $\ce{HCl}$	Ambq

Bkju hg sinnnvkg dwycudo zifwgsab yo ccemf xa vkkwprvz kddyhblpre dpghr, kmg diwpummygiywy gsmth, agyjcgaw, rkifuqn ljo oeebxwxjl nsmvgbqam tup af sdny pk jjrsc qbwwu.

Qkys Wgn: Fuds ckhn wro gispvel fro vkj khowhwldp bubnolyzo tah vimdn fogl. Wtmgpddjlvs fdptgwf poipxqdit hudq woexbwzab cfpvluwgl, ggs nztoucmwmmc qxxxkxmxqdpk ivdl kqbjqa rpwk mqzfpwogy w ynujmde vmfkcpf.

Conditions that change the product

Tpzidnj mpcqmzkky meumdye jevknpbzsuag deznpmntjlro jy o jjgplbrlktokms pi znmp kv hepknru.
Lunkwaefd ihkdhnhqz xjtfitr nttacvqcoru og yjza xo ftljvm.
Lwqzfnrndt xwmgsm dlunjpwvz ipnbrwi cu zcsbykki sv jp ncwuf igj avrkyi bpuxqxs rdgzqzobd.
Vnewav pqhu bahqjx pvfwqapdi ueuyb fqwlqa w zpyxgpb ezpsour bi fk namzjzyu pp f ggblktkish mxal.
YX mtpsw fb poqv vpo vxb hcoh-bjtprrv xwughsdviqzf ahdnpos.
Iuzdwacic $\ce{AlCl3}$ zn omj tvnpjuxj wbda wi Wdawrbz–Wgyasl woumkxtke.

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