1、Organic Chemistry,Some significant organic chemical terms,hydrocarbons; saturated hydrocarbon; unsaturated hydrocarbon; conjugate (conjugation); （碳氢化合物，烃，饱和，不饱和，共轭）,Types of Reaction: substitution (alkylation, halogenation etc)（取代，如烷基化，卤代）; addition（加成）; elimination（消去）; condensation（缩合）; polymeriza
2、tion（聚合）; oxidation（氧化）; reduction（还原）.,degradation（降解）; rearrangement（重排）; replacement（置换） ; pericyclic reaction (cycloaddition reaction; electrocyclic reaction; sigmatropic rearrangement)（周环反应，包括:环加成，电环化，-重排）,Electrophile (electrophilic)（亲电试剂，亲电的）; nucleophile (nucleophilic)（亲核试剂，亲核的）; Carbocation
3、（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）;,Reactivity（反应活性）; Attack（进攻）; leaving group（离去基团）; protecting group（保护基）; catalyst（催化剂）; Kinetic（动力学的）; thermodynamic（热力学的）.,cis-trans isomer; optical isomer (enantiomer); （顺-反异构体，光学异构体（光学对映体） asymmetric; chiral; c
4、hirality; （不对称，手性的，手性）,racemic mixture; meso compound; （外消旋体，内消旋体） stereoselective reaction; stereospecific reation; regioselective reaction; steric hindrance; steric effects; （立体阻碍（位阻），立体效应 ）,reflux; stir; azeotrope; （回流，搅拌，恒、共沸物） separation; filter; distillation; fraction; chromatography; （分离，过滤，蒸
5、馏，分馏，色谱） extraction; precipitate; recrystallization; （萃取，沉淀，重结晶）,Terms related to the synthetic experiment,Ground joint; Flask (three-necked, round-bottom, conical, filter, suction, volumetric); Condenser (air, reflux, ball, coil); distilling head (claisen); adaptor (vacuum); Beaker; funnel (buchner
6、, separatory, long-stem, stemless, dropping, sintered glass); Bottle (weighing, washing, dropping, gas-washing); drying tube (tower, desiccator, vacuum desiccator);,Prefix-Parent-SuffixNomenclature of parent part-Nomenclature of alkanes and alkyl substituentsStraight-chain alkanesStraight-chain alka
7、nes are named 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.,An alkyl substituent (or an alkyl group) is an alkane from which a single hydrogen has been removed. Alkyl substituents are
8、 named by replacing the “ane” suffix of the alkane with “yl”. The letter “R” is used to indicate any alkyl group. Thus CH3- has the name of methyl, while the group of CH3CH2- was named ethyl.,Number Molecular Name Name in Alkyl of carbons formula Chinese substituents1 CH4 Methane 甲烷 Methyl 2 C2H6 Et
9、hane 乙烷 Ethyl3 C3H8 Propane 丙烷 Propyl4 C4H10 Butane 丁烷 Butyl5 C5H12 Pentane 戊烷 Pentyl6 C6H14 Hexane 己烷 Hexyl7 C7H16 Heptane 庚烷 Heptyl8 C8H18 Octane 辛烷 Octyl9 C9H20 Nonane 壬烷 Nonyl10 C10H22 Decane 癸烷 Decyl11 C11H24 Undecane 十一烷 Undecyl12 C12H26 Dodecane 十二烷 Dodecyl13 C13H28 Tridecane 十三烷 Tridecyl20 C
10、20H42 Icosane 二十烷 Icosyl 21 C21H44 Heneicosane 二十一烷 Heneicosyl30 C30H62 Triacontane 三十烷 Triacontyl,Branched-chain alkanes 3-ethyl-3-methylhexane,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 Hex (a)- 六取代 Hept (a)- 七取代 Oct
11、 (a)- 八取代 Nona- 九取代 Deca- 十取代,2,6-dimethyloctane not 2-ethyl-6-methylheptane3-ethyl-2-methylhexane not 3-isopropylhexane,Some useful prefixes used to name branched alkanes (Common names)(normal) n- 正 (isomer) iso- 异 neo- 新 primary 伯，一级 (secondary ) sec- 仲，二级 (tertiary) tert- 叔，三级 quaternary 季，四级,n-p
12、entane 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-methylpropanamine,Cyclic alkanes (cycloalkanes)e.g. cylcopropane, cyclopentane, and cyclohexyl etc,Nomenclature of acyclic hy
13、drocarbons with one double or triple bondAcyclic hydrocarbons having one double or triple bond are named by replacing the ending “-ane” of the name of the corresponding alkane with the ending “-ene” or “-yne” . (alkene) (alkyne) e. g.(butane) butene butene butynetrans-2-butene cis-2-butene 3-methyl-
14、1- butyne,The univalent radical derived from acyclic alkene or alkyne has the endings “-enyl” or “-ynyl”, (alkene alkenyl) (alkyne alkynyl), and the position of the double or triple bond is indicated where necessary. (unlike alkane alkyl) e. g. 1-propenyl 2-butenylethynyl 2-propynyl,The following no
15、n-systematic names are retained Ethylene (乙烯） Allene （丙二烯） Acetylene （乙炔） Isoprene （异戊二烯）Vinyl （乙烯基） Allyl （烯丙基） Isopropenyl （异丙烯基）,Nomenclature of acyclic hydrocarbons with two or more double or triple bonds Two or more double bonds: the ending will be “-adiene”, “-atriene” etc. (alkadiene) Two or
16、more triple bonds: the ending will be “-adiyne”, “-atriyne” etc. (alkadiyne) e. g.2-methyl-1,3-butadiene propadiene 2,5-dimethyl-2,4,6-octatriene 3-ethyl-4-methyl-1,6-heptadiyne,Nomenclature 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
17、基 二甲苯基 苯乙烯基 异丙苯基 均三甲苯基 苄基 Phenyl tolyl xylyl styryl cumenyl mesityl benzyl,Common names retained for the disubstituted benzeneortho-, o- 邻 meta-, m- 间 para-, p- 对,m-methylbenzyl m-tolyl 3,4-dimethylphenyl 3-methylbenzyl 3-tolyl o-styryl p-cumenyl 3,5-dimethyl-4-ethylphenyl2-styryl 4-cumenyl,Some imp
18、ortant Families of organic molecules Saturated hydrocarbons: such as: Alkanes; cycloalkanes; Un-saturated hydrocarbons: such as: alkenes; alkynes; cycloalkenes; cycloalkynes; cycloalkadienes; cycloalkadiynes; Aromatic compouds: benzene; biphenyl; naphthalene and other fused and polycyclic aromatic h
19、ydrocarbons; Compounds with functional groups: alkyl halides （卤代烃）; alcohols（醇）; phenols（酚）; ethers（醚）; amines（胺）; Compounds with functional groups: aldehydes（醛）; ketones（酮）; quinones（醌）; carboxylic acids（羧酸）; esters（酯）; acyl halides（酰卤）; acid anhydrides（酸酐） amides（酰胺）; imides（亚胺）;,Compounds with fu
20、nctional groups: alkyl halides （卤代烃）; alcohols（醇）; phenols（酚）; ethers（醚）; amines（胺）etc.alkyl halides R-X halogen (-halo) (-Cl, -Br, -F, -I) Alcohols R-OH hydroxy group (-OH) Phenols Ar-OH hydroxy group (-OH) Ethers R-O-R Alkoxy group (O-R) Amines R-NH2 amino group (NH2),Alkyl halides (haloalkane or
21、alkyl halide)Alkyl halides are classified as primary, secondary, or tertiary depending on the carbon to which the halogen is attached.,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, alky
22、l halides are named as substituted alkanes. The substituted prefix names for the halogens end in “o”(fluoro, chloro, bromo, iodo). (haloalkane),Nomenclature of alcoholsAlcoholsThe common names, similar to alkyl halides, are obtained by citing the name of the alkyl group to which the OH group is atta
23、ched, 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),Nomenclature of aminesAmines are compounds in which one or more hydrogen of ammonia have been replaced by alkyl groups.
24、 There are primary, secondary, and tertiary amines. This classification depends on how many alkyl groups are bonded to the nitrogen. (!not carbon),The 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 a
25、s one word. (alkylamine)e. g.,There are two IUPAC approved way to name an amine. It can be named as a substituted alkane using the prefix “amino” to designate the amine substituent. (?aminoalkane)It also can been named with a functional group suffix- “amine”. The “e” at the end of the alkane name is
26、 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. (N-alkyl)alkanamine,Amines with four alkyl groups bonded to the nitrogen-and therefore a positive charge on the ni
27、trogen-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. alkylammonium halide (or hydroxide etc),Nomenclature of ethers symmetrical ether and asymmetrical eth
28、er. e. g.,The 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)The IUPAC system names an ether as an alkane that bears an a
29、lkoxy substituent. Alkoxy substituents are named by removing the “yl” from the name of the alkyl substituent and adding “oxy”. (alkoxyalkane),methoxy,ethoxy,1-methylethoxy,1,1-dimethylpropoxy,A carbonyl group （羰基） is a carbon doubly bonded to an oxygen and an acyl group （酰基） is a carbonyl group atta
30、ched to an alkyl substituent. A benzoyl group （苯甲酰基） is a carbonyl group attached to a benzene ring.,Nomenclature of aldehydes and ketones The common name of an aldehyde is the same as carboxylic acid (derived from some Latin words). (Latin+aldehyde)The IUPAC name of an aldehyde is obtained by remov
31、ing the “e” from the alkane name and adding “-al”. (alkanal),If the aldehyde group is attached to a ring, the aldehyde is named by adding “carbaldehyde” to the name of the ring. (cycloalkanecarbaldehyde),phenylmethanal,Nomenclature of ketones Common name: Only a few ketons have common names, such as
32、 acetone (like aldehyde). Common names are also used for phenyl-substituted ketones. They are called phenones. (+ one) IUPAC name: Ketones are named in the IUPAC system by removing the “e” from the alkane name and adding “-one”. (alkanone) Derived name: Like ethers, R-CO-R can be named by citing the
33、 names of the two alkyl substituents (in alphabetical order) followed by the word “ketone”. (alkylalkyl ketone),Common nameIUPAC nameDerived name,Nomenclature of carboxylic acids and its derivatives,X= OH, a carboxylic acid X= halogen, an acyl halide X=OR, an ester X= OCOR, an acid anhydride X= NRR,
34、 an amide,Nomenclature of carboxylic acidsa carboxyl groupThe functional group of a carboxylic acid is called a carboxyl group. Long-chain carboxylic acids are called “fatty acids”.,Common name: Carboxylic acids (6) are frequently called by their common names. They are named by adding “Latin prefix”
35、 before “acid”. ? what is carbon?IUPAC name: a carboxylic acid is named by replaceing the “e” ending of the alkane name with “oic acid”. (alkanoic acid) Carboxylic 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 comp
36、ound.,benzoic acid,Nomenclature of acyl halidesAcyl halides are named by using the acid name and replacing the “ ic acid” with “ yl halide” (alkanoyl halide) , or by replacing “ carboxylic acid ” with “ carbonyl halide ” (cycloalkanecarbonyl halide),benzoyl chloride,Nomenclature of acid anhydrides ?
37、 Do you know the meaning of “anhydride”R = R, a symmetrical anhydrideR R, a mixed anhydride,Symmetrical 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”.
38、,Nomenclature of estersIn naming an ester, the name of the group attached to the “carboxyl oxygen” is stated first. This is followed by the name of the acid with “-ic acid” replaced by “-ate”. Salts of carboxylic acids are named in the same way. (R alkyl R alkanoate),ethyl acetate,Nomenclature of am
39、idesA primary amide a secondary amide a tertiary amideAmides are named by using the acid name, replacing “ oic acid” or “ -ic acid” with “amide”, or by replacing “ carboxylic acid” with “ carboxamide”.(alkanamide) or (cycloalkanecarboxamide),Nomenclature of nitriles In common nomenclature, nitriles
40、are named by replacing “ ic acid” with “ -onitrile”, or they are named as “alkyl cyanide”. (alkyl cyanide)In IUPAC nomenclature, nitriles are named by adding “ -nitrile” to the alkane name. (alkanenitrile),Halogen (卤素) Fluorine (氟) Chlorine (氯） Bromine (溴) Iodine (碘),Noble gas (惰性气体) Argon (氩),Alkali metals (碱金属) Lithium (锂) Sodium (钠) Potassium (钾),Alkaline earths (碱土) Magnesium (镁) Calcium (钙),Aluminum (铝) Tin (锡) Lead (铅),transition metals:,Titanium (钛) Chromium (铬) Manganese (锰) Iron (铁) Cobalt (钴),Nickle (镍) Copper (铜) Zinc (锌) Silver (银) Platinum (铂),
