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1、organic chemistry some significant organic chemical termsnhydrocarbons; saturated hydrocarbon; unsaturated hydrocarbon; conjugate (conjugation); (碳氢化合物,烃,饱和(碳氢化合物,烃,饱和 ,不饱和,不饱和 ,共轭),共轭)types of reaction: substitution (alkylation, halogenation etc)(取代,如烷(取代,如烷基化,卤代)基化,卤代); addition(加成)(加成); eliminati

2、on(消去)(消去); condensation(缩合)(缩合); polymerization(聚合)(聚合); oxidation(氧化)(氧化); reduction(还原)(还原).ndegradation(降解)(降解); rearrangement(重排)(重排); replacement(置换)(置换) ; npericyclic reaction (cycloaddition reaction; electrocyclic reaction; sigmatropic rearrangement)(周环反应,包括(周环反应,包括:环加成,电环化,环加成,电环化,-重排)重排)el

3、ectrophile (electrophilic)(亲电试剂,亲电的); nucleophile (nucleophilic)(亲核试剂,亲核的);carbocation(碳正离子); carbanion(碳负离子); radical(游离基,free ,自由基); intermediate(中间体); substituent(取代基);nreactivity(反应活性(反应活性); attack(进攻)(进攻); leaving group(离去基团)(离去基团); protecting group(保护基)(保护基); catalyst(催化剂)(催化剂); nkinetic(动力学的)

4、(动力学的); thermodynamic(热力学(热力学的)的).cis-trans isomer; optical isomer (enantiomer); (顺(顺-反异构体,光学异构体(光学对映体)反异构体,光学异构体(光学对映体)asymmetric; chiral; chirality; (不对称,手性的,手性)(不对称,手性的,手性)nracemic mixture; meso compound; (外消旋体,内消旋体)(外消旋体,内消旋体)nstereoselective reaction; stereospecific reation; regioselective reac

5、tion; nsteric hindrance; steric effects;(立体阻碍(位阻),立体效应(立体阻碍(位阻),立体效应 )reflux; stir; azeotrope; (回流,搅拌,恒、共沸物)(回流,搅拌,恒、共沸物)nseparation; filter; distillation; fraction; chromatography;(分离,过滤,蒸馏,分馏,色谱)(分离,过滤,蒸馏,分馏,色谱)nextraction; precipitate; recrystallization; (萃取,沉淀,重结晶)(萃取,沉淀,重结晶)terms related to the

6、 synthetic experiment reducing adapterbeakererlenmeyer (conical) flaskthree-neck round-bottom flaskround-bottom flasksstopperallihn (ball)condenserliebig condenserseparatory funneldropping funnelsintered glass funnelgrahams (coil) condenserfunnelfiltering flasksvacuum-distilling adapterclaisen adapt

7、erspestlemortarsplash-guardthree-way adaptersbuchner funnelstrapcruciblesvolumetric flasks ground joint; nflask (three-necked, round-bottom, conical, filter, suction, volumetric); ncondenser (air, reflux, ball, coil); distilling head (claisen); adaptor (vacuum); nbeaker; funnel (buchner, separatory,

8、 long-stem, stemless, dropping, sintered glass);nbottle (weighing, washing, dropping, gas-washing); drying tube (tower, desiccator, vacuum desiccator); prefix-parent-suffixnomenclature of parent part-nomenclature of alkanes and alkyl substituentsstraight-chain alkanes straight-chain alkanes are name

9、d by counting the number of carbon atoms in the chain and adding the family suffix-ane. thus pentane is the five-carbon alkane, and hexane is the six-carbon alkane. nan alkyl substituent (or an alkyl group) is an alkane from which a single hydrogen has been removed. nalkyl substituents are named by

10、replacing the “ane” suffix of the alkane with “yl”. the letter “r” is used to indicate any alkyl group. nthus ch3- has the name of methyl, while the group of ch3ch2- was named ethyl. number molecular name name in alkylof carbons formula chinese substituents 1 ch4methane甲甲烷烷 methyl 2 c2h6ethane乙乙烷烷 e

11、thyl 3 c3h8propane丙丙烷烷 propyl 4 c4h10butane 丁丁烷烷 butyl 5 c5h12pentane戊戊烷烷 pentyl 6 c6h14hexane己己烷烷 hexyl 7 c7h16heptane 庚庚烷烷 heptyl 8 c8h18octane辛辛烷烷 octyl 9 c9h20nonane壬壬烷烷 nonyl 10 c10h22decane癸癸烷烷 decyl 11 c11h24undecane十一十一烷烷 undecyl 12 c12h26dodecane十二十二烷烷 dodecyl 13 c13h28tridecane十三十三烷烷 tride

12、cyl 20 c20h42icosane二十二十烷烷 icosyl 21 c21h44heneicosane二十一二十一烷烷 heneicosyl 30 c30h62triacontane三十三十烷烷 triacontylbranched-chain alkanes 3-ethyl-3-methylhexanech3ch2cch2ch2ch3ch2ch3ch3 some useful prefixes for indicating the number of substituent groupsmono-单取代, 一取代di- 二取代tri-三取代tetra-四取代pent (a)-五取代he

13、x (a)-六取代hept (a)-七取代oct (a)-八取代nona-九取代deca-十取代2,6-dimethyloctanenot2-ethyl-6-methylheptane3-ethyl-2-methylhexanenot3-isopropylhexanech3chch2ch2 ch2chch3ch2ch3ch3ch3ch2chch2 ch2ch3chch3ch3nsome useful prefixes used to name branched alkanes (common names)(normal) n- 正(isomer) iso- 异neo- 新primary 伯,一

14、级(secondary ) sec- 仲,二级(tertiary) tert- 叔,三级quaternary 季,四级 n-pentane neopentane isobutane 正戊烷 新戊烷 异丁烷 pentane 2,2-dimethylpropane 2-methylpropanetert-butanol isobutanamine sec-butanamine 叔丁醇 异丁胺 仲丁胺2-methyl-2-propanol 2-methylpropanamine 1-methylpropanaminech3(ch2)3ch3ch3cch3ch3ch3ch3chch3ch3ch3cch

15、3ohch3ch3chch2nh2ch3ch3ch2chnh2ch3cyclic alkanes (cycloalkanes)e.g. cylcopropane, cyclopentane, and cyclohexyl etcchcchch3ch3ch3ch3ch3ch3nomenclature of acyclic hydrocarbons with one double or triple bond acyclic hydrocarbons having one double or triple bond are named by replacing the ending “-ane”

16、of the name of the corresponding alkane with the ending “-ene” or “-yne” . (alkene) (alkyne)e. g. (butane) butene butene butyne trans-2-butene cis-2-butene 3-methyl-1- butyne the univalent radical derived from acyclic alkene or alkyne has the endings “-enyl” or “-ynyl”, (alkene alkenyl) (alkyne alky

17、nyl), and the position of the double or triple bond is indicated where necessary. (unlike alkane alkyl)e. g. 1-propenyl 2-butenyl ethynyl 2-propynylchchch3ch3chchch2chcchcch2the following non-systematic names are retainednethylene (乙烯)nallene (丙二烯)nacetylene (乙炔)nisoprene (异戊二烯)nvinyl (乙烯基)nallyl (烯

18、丙基)nisopropenyl (异丙烯基)chchch2ch2ch2cch2ch2chch2chch2ch3cch2nomenclature of acyclic hydrocarbons with two or more double or triple bondsntwo or more double bonds: the ending will be “-adiene”, “-atriene” etc. (alkadiene)ntwo or more triple bonds: the ending will be “-adiyne”, “-atriyne” etc. (alkadiy

19、ne)e. g. 2-methyl-1,3-butadiene propadiene 2,5-dimethyl-2,4,6-octatriene 3-ethyl-4-methyl-1,6-heptadiynech2cch2chchch3ch3nomenclature of monocyclic aromatic hydrocarbons 苯 甲苯 二甲苯 苯乙烯 异丙苯 均三甲苯 benzene toluene xylene styrene cumene mesitylene苯基 甲苯基 二甲苯基 苯乙烯基 异丙苯基 均三甲苯基 苄基phenyl tolyl xylyl styryl cume

20、nyl mesityl benzylch3ch3ch3chch2ch3ch3ch3ch3ch3ch3ch3ch3chch2ch3ch3ch3ch3ch3ch2common names retained for thedisubstituted benzeneortho-, o-邻meta-, m-间para-, p-对 m-methylbenzyl m-tolyl 3,4-dimethylphenyl3-methylbenzyl 3-tolyl o-styryl p-cumenyl 3,5-dimethyl-4- ethylphenyl 2-styryl 4-cumenyl ch3ch3ch3

21、ch2chch2ch3ch3ch3ch3ch2ch3 some important families of organic moleculesnsaturated hydrocarbons: such as: alkanes; cycloalkanes; nun-saturated hydrocarbons: such as: alkenes; alkynes; cycloalkenes; cycloalkynes; cycloalkadienes; cycloalkadiynes; naromatic compouds: benzene; biphenyl; naphthalene and

22、other fused and polycyclic aromatic hydrocarbons; ncompounds with functional groups: alkyl halides (卤代烃); alcohols(醇); phenols(酚); ethers(醚); amines(胺); ncompounds with functional groups: aldehydes(醛); ketones(酮); quinones(醌); carboxylic acids(羧酸); esters(酯); acyl halides(酰卤); acid anhydrides(酸酐) am

23、ides(酰胺); imides(亚胺); compounds with functional groups: alkyl halides (卤代烃); alcohols(醇); phenols(酚); ethers(醚); amines(胺)etc.nalkyl halidesr-x halogen (-halo) (-cl, -br, -f, -i)nalcoholsr-oh hydroxy group (-oh)nphenolsar-oh hydroxy group (-oh)nethersr-o-r alkoxy group (o-r)naminesr-nh2 amino group

24、(nh2) alkyl halides (haloalkane or alkyl halide) alkyl halides are classified as primary, secondary, or tertiary depending on the carbon to which the halogen is attached. ch3ch2brch3chch3brch3cbrch3ch3a primary alkyl halidea secondary alkyl halide a tertiary alkyl halide ethyl bromide tert-butyl bro

25、mide sec-propyl bromide the common names of the alkyl halides are obtained by citing the name of the alkyl group followed by the name of the halogen. (alkyl halide) in the iupac system, alkyl halides are named as substituted alkanes. the substituted prefix names for the halogens end in “o”(fluoro, c

26、hloro, bromo, iodo). (haloalkane)ch3ch2clch3chch3fch3cbrch3ch3 sec-propyl fluoride ethyl chloride tert-butyl bromidech3i methyl iodide 2-fluoropropane chloroethane2-bromo-2-methylpropane iodomethanenomenclature of alcohols alcohols the common names, similar to alkyl halides, are obtained by citing t

27、he name of the alkyl group to which the oh group is attached, followed by the word “alcohol”. (alkyl alcohol) the iupac name for an alcohol is obtained by removing the “e” from the name of the alkane and adding the suffix “ol”. (alkanol)ch3ch2ohch3chch3ohch3cohch3ch3sec-propyl alcohol (isopropyl alc

28、ohol) ethyl alcoholtert-butyl alcohol2-propanol ethanol2-methyl2-propanolnomenclature of amines amines are compounds in which one or more hydrogen of ammonia have been replaced by alkyl groups. there are primary, secondary, and tertiary amines. this classification depends on how many alkyl groups ar

29、e bonded to the nitrogen. (!not carbon)rnh2a secondary amine a primary aminea tertiary aminernhrrnrrrcrrnh2rcrroh a primary amine a tertiary alcoholnthe common name of a amine is obtained by citing the names of the alkyl groups bonded to the nitrogen in alphabetical order. the entire name is written

30、 as one word. (alkylamine) e. g. ch3nch3ch3ch3nch2ch2ch2ch3ch2ch3ch3nch2ch3chch2ch2ch3ch2cltrimethylaminebutylethylmethylamineno common namenthere are two iupac approved way to name an amine. nit can be named as a substituted alkane using the prefix “amino” to designate the amine substituent. (?amin

31、oalkane)1.it also can been named with a functional group suffix- “amine”. the “e” at the end of the alkane name is replaced by “amine”. the names of substituents bonded to the nitrogen are preceded by an n (in italic) to indicate that the substituent is bonded to a nitrogen rather than to a carbon.

32、(n-alkyl)alkanaminech3nch3ch3ch3nch2ch2ch2ch3ch2ch3ch3nch2ch3chch2ch2ch3ch2cldimethylaminomethane1-(ethylmethylamino)butane1-chloro-2-(ethylmethylamino)pentaneorn,n-dimethylmethanamineorn-ethyl-n-methylbutanamineor1-chloro-n-ethyl-n-methyl-2-pentanaminetrimethylaminebutylethylmethylamineno common na

33、menamines with four alkyl groups bonded to the nitrogen-and therefore a positive charge on the nitrogen-are called quaternary ammonium salts. their names are obtained by citing the names of the alkyl groups in alphabetical order as a prefix to “ammonium”, followed by the name of the counterion. alky

34、lammonium halide (or hydroxide etc)ch3n+ch3ch3ch3ch3n+ch2ch2ch2ch3ch2ch3ch3ch3n+ch2ch3chch2ch2ch3ch2clch3oh-cl-br-tetramethylammonium hydroxide(1-chloromethyl)butylethyldimethylammonium bromidebutylethyldimethylammoniumchloridenomenclature of etherssymmetrical ether and asymmetrical ether. e. g.rorr

35、ora symmetrical etheran asymmetrical ethernthe common name of an ether is obtained by citing the names of the two alkyl substituents (in alphabetical order) followed by the word “ether”. the smallest ethers are almost always named by their common names. ( alkylalkyl ether) nthe iupac system names an

36、 ether as an alkane that bears an alkoxy substituent. alkoxy substituents are named by removing the “yl” from the name of the alkyl substituent and adding “oxy”. (alkoxyalkane)ch3oh3ch2coch2ch3ch3och2ch3ch3ochch2ch3ch3ethoxyethanemethoxyethane2-methoxybutanemethoxycyclohexanech3och3ch2och3choch3ch2c

37、och3ch3ch3methylethyl1-methylethyl1,1-dimethylpropylmethoxy ethoxy 1-methylethoxy 1,1-dimethylpropoxy diethyl ether( ethyl ether)ethylmethyl ethersec-butylmethyl ethercyclohexylmethyl ether a carbonyl group (羰基) is a carbon doubly bonded to an oxygen and an acyl group (酰基) is a carbonyl group attach

38、ed to an alkyl substituent. a benzoyl group (苯甲酰基) is a carbonyl group attached to a benzene ring. orocoa carbonyl groupan acyl groupa benzoyl groupnomenclature of aldehydes and ketonesnthe common name of an aldehyde is the same as carboxylic acid (derived from some latin words). (latin+aldehyde)nth

39、e iupac name of an aldehyde is obtained by removing the “e” from the alkane name and adding “-al”. (alkanal)ohh3cohcohhformaldehydeacetaldehydebenzaldehydemethanalethanalphenylmethanalnif the aldehyde group is attached to a ring, the aldehyde is named by adding “carbaldehyde” to the name of the ring

40、. (cycloalkanecarbaldehyde)ohohohch3ohch2ch3ch3benzenecarbaldehydecyclohexanecarbaldehyde4-methylbenzenecarbaldehyde5-ethyl-4-methylcyclohexanecarbaldehydephenylmethanalnomenclature of ketonesncommon name: only a few ketons have common names, such as acetone (like aldehyde). common names are also us

41、ed for phenyl-substituted ketones. they are called phenones. (+ one)niupac name: ketones are named in the iupac system by removing the “e” from the alkane name and adding “-one”. (alkanone)nderived name: like ethers, r-co-r can be named by citing the names of the two alkyl substituents (in alphabeti

42、cal order) followed by the word “ketone”. (alkylalkyl ketone)common nameiupac namederived nameoch2ch3h3coch3coch3h3coch3acetoneacetophenonebutyrophenonepropanonephenylethanonephenylbutanone2-butanonebutyryl benzene or dimethyl ketonemethyl phenyl ketonephenyl propyl ketoneethyl methyl ketone nomencl

43、ature of carboxylic acids and its derivativesoxrx= oh, a carboxylic acidx= halogen, an acyl halide x=or, an esterx= ocor, an acid anhydridex= nrr, an amide nomenclature of carboxylic acids a carboxyl group the functional group of a carboxylic acid is called a carboxyl group. long-chain carboxylic ac

44、ids are called “fatty acids”. oohncommon name: carboxylic acids (6) are frequently called by their common names. they are named by adding “latin prefix” before “acid”. ? what is carbon?n iupac name: a carboxylic acid is named by replaceing the “e” ending of the alkane name with “oic acid”. (alkanoic

45、 acid)ncarboxylic acids in which a carboxyl group is attached to a cyclic compound can be named by adding “carboxylic acid” to the name of the cyclic compound. hcoohch3coohh3ch2ccoohhc=ch2coohformic acidacetic acidpropionic acidacrylic acidmethanoic acidethanoic acidpropanoic acidpropenoic acidcoohc

46、oohcoohch3ch3coohcoohcoohbenzoic acidbenzenecarboxylic acidcyclohexanecarboxylic acid2,4-dimethylcyclopentane-carboxylic acid1,2,4-benzenetricarboxylic acidnomenclature of acyl halides acyl halides are named by using the acid name and replacing the “ ic acid” with “ yl halide” (alkanoyl halide) , or

47、 by replacing “ carboxylic acid ” with “ carbonyl halide ” (cycloalkanecarbonyl halide)methanoyl bromideethanoyl chloridepropanoyl bromidepropenoyl chlorideformyl bromideacetyl chloridehcobrch3coclh3ch2ccobrhc=ch2coclmethanoic acidethanoic acidpropanoic acidpropenoic acidcoclcobrcobrch3ch3benzenecar

48、boxylic acidcyclohexanecarboxylic acid2,4-dimethylcyclopantane-carboxylic acidbenzoyl chloridebenzenecarbonyl chloridecyclohexanecarbonyl bromide2,4-dimethylcyclopentane-carbonyl bromidenomenclature of acid anhydrides? do you know the meaning of “anhydride” r = r, a symmetrical anhydride r r, a mixe

49、d anhydrider-c-o-c-roonsymmetrical anhydrides are named by using the acid name and replacing “acid” with “anhydride”, mixed anhydrides are named by stating the name of both acid groups in alphabetical order followed by “anhydride”.ch3c-o-chch3c-o-cch3ooch3chch2c-o-cch2ch3ooooch3ethanoic anhydrideethanoic methoic anhydride3-methylbutanoic propanoic anhydrideacetic anhydrideacetic formic anhydridenomenclature of esters in naming an ester, the name of the group attached to the “carboxyl oxygen” is stated first. this is followed by

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