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浜嗚В鐠�(hu谩n)鐑风兇鍛藉悕鍙婂弽鎳�(y墨ng)鍙婄挵(hu谩n)宸辩兎宸ユキ(y猫)渚嗘簮;鎺屾彙灏忕挵(hu谩n)鐨� 寮靛姏鍙婄┅(w臎n)瀹氭€�銆佹寮�/鑸瑰紡妲�(g貌u)鍨�銆乤 閸�銆乪 閸点€� 绗笁绔� 鐑兇 鎺屾彙鍠儻鐑寸殑閲嶈鍖栧(xu茅)鎬ц唱(zh矛)鍙婂弽鎳�(y墨ng)瑕�(gu墨)寰� 鎺屾彙鍠儻鐑寸殑鍒嗛銆佸懡鍚�銆佺祼(ji茅)妲�(g貌u)鍙婂悓鍒嗙暟妲�(g貌u)鐝�(xi脿n)璞� 3.1 鐔熸倝鐑殑鍛藉悕銆佺祼(ji茅)妲�(g貌u)銆佺暟妲�(g貌u)楂�銆佺墿鐞嗘€ц唱(zh矛) 3.1.1 鐞嗚В鐑兇鐨勭祼(ji茅)妲�(g貌u) SP2 闆滃寲銆佅€ 閸� 3.1.2 鎺屾彙鐑兇鐨勫悓鍒嗙暟妲�(g貌u)楂斿拰鍛藉悕锛氱⒊鏋剁暟妲�(g貌u)銆佷綅缃暟妲�(g貌u)銆� 闋嗗弽鐣版(g貌u)銆佺郴绲�(t菕ng)鍛藉悕娉�(鐑熀鐨勫懡鍚�)銆侀爢鍙嶇暟妲�(g貌u)楂旂殑鍛藉悕銆侀爢 /鍙�銆乑/E 3.2 鐑兇鐨勫弽鎳�(y墨ng) 鎺屾彙瑕浕鍔犳垚鍙嶆噳(y墨ng)姝风▼銆佹捍閹撻洟瀛�銆佽Κ闆昏│鍔�銆佺⒊姝i洟瀛� 鍙婂叾绌�(w臎n)瀹氭€с€侀Μ姘忚(gu墨)鍓�銆佽獦灏�(d菐o)鏁堟噳(y墨ng)锛屾父姝峰熀鍔犳垚鍙嶆噳(y墨ng)姝风▼銆侀亷 姘у寲鐗╂晥鎳�(y墨ng)鐨勮В閲嬮Μ鐖惧彲灏煎彲澶(gu墨)鍓囥€佸姞鎴愬弽鎳�(y墨ng)涓殑纰虫闆� 瀛�銆佺⒊姝i洟瀛愮殑绲�(ji茅)妲�(g貌u)鍙婃€ц唱(zh矛)銆佷簩鐑殑 1锛�4 鍔犳垚鍜岀挵(hu谩n)鍔犳垚鍙嶆噳(y墨ng); 3.2.1 鍔犳垚鍙嶆噳(y墨ng)锛氬偓鍖栧姞姘€佽垏涔欑〖鐑风殑鍔犳垚銆佸姞 X2銆佸姞 HX (棣皬(Markovnikow)瑕�(gu墨)鍓�銆侀亷姘у寲鐗╂晥鎳�(y墨ng))銆佸姞 H2SO4銆侀吀 鍌寲鍔� H2O銆佽垏鏈夋(j墨)閰搁唶閰氬姞鎴�銆佸姞 HOCl銆佽嚜鐢卞熀鍔犳垚銆� 3.2.2 姘у寲锛氱挵(hu谩n)姘у寲銆侀珮閷抽吀閴€姘у寲鍜岃嚟姘у寲 3.2.4 伪鈥�?d煤)婀擃厫鎷ユ煚u浠e弽鎳�(y墨ng) 3.2.5 浜嗚В鑱氬悎鍙嶆噳(y墨ng) 3.3 鐑殑渚嗘簮鍜屽埗鍌� 3.3.1 鎺屾彙閱囩殑鑴按銆侀沟浠g兇鑴沟鍖栨矮銆侀劙浜岄沟浠g兎鑴沟绱� 3.3.2 浜嗚В閲嶈鐨勭儻鐑达細涔欑儻銆佷笝鐑� 3.4 鎺屾彙鍏辫粵浜岀儻鐑寸壒鍒ユ槸 1锛�3鈥斾竵浜岀儻鐨勬€ц唱(zh矛)銆佺祼(ji茅)妲�(g貌u)鐗� 榛�(di菐n)鍙婄敤閫� 3.4.1 鍒嗛鍜屽懡鍚�銆佸叡杌涗簩鐑兇鐨勫垎瀛愮祼(ji茅)妲�(g貌u)锛氶洟鍩熼嵉銆侀洟鍩� 鑳�銆佸叡杌涙晥鎳�(y墨ng) 3.4.2 鍏辫粵浜岀儻鐑寸殑鍖栧(xu茅)鐗规€э細鍔犳垚鍙嶆噳(y墨ng)(1锛�2 鍜� 1锛�4鈥斿姞 鎴�)銆佺媱鑰虫柉鈥旈樋鐖惧痉(Diels-Alder)鐠�(hu谩n)鍔犳垚鍙嶆噳(y墨ng)銆佽仛鍚堝弽鎳�(y墨ng) 3.4.3 閲嶈鐨勪簩鐑兇锛氫竵浜岀儻鍜岀暟鎴婁簩鐑締婧愯垏鍙嶆噳(y墨ng) 绗洓绔� 鐐旂兇 4.1 鎺屾彙鐐旂兇鐨勫垎椤炪€佸懡鍚�锛岀祼(ji茅)妲�(g貌u)(sp 闆滃寲绛�)鍙婂悓鍒嗙暟妲�(g貌u) 鐝�(xi脿n)璞� 4.2 鎺屾彙鐐旂兇閲嶈鐗╃悊鍖栧(xu茅)鎬ц唱(zh矛)鍒跺倷鏂规硶鍙婂弽鎳�(y墨ng)瑕�(gu墨)寰�, 濡� 鐐旂殑鍙嶆噳(y墨ng)锛氬姞鎴�銆佹哀鍖栧強鏈 H 鐨勬椿鎬х瓑 4.2.1 鍔犳垚鍙嶆噳(y墨ng)锛氬偓鍖栧姞姘�銆佷箼纭肩兎銆佸姞 X2銆佸姞 HX銆佸姞 H2O銆丠CN銆丠OCl; 鑸囧惈鈥滄椿鎬ф矮鈥濈殑鏈夋(j墨)鐗╃殑瑕牳鍔犳垚;鑸囧牽 閲戝爆(K,Na,Li)鍙婃恫姘ㄩ倓鍘熷姞鎴�; 4.2.2 鐐旈嵉纰充笂鐨勬矮鍘熷瓙鐨勬€ц唱(zh矛)鍜岄憭瀹氾細寮遍吀鎬с€侀噾灞倲鍖� 鐗╁強鐑村寲(纰宠矤(f霉)闆㈠瓙) 4.2.5 鎺屾彙鐐旂兇鍜岀儻鐑寸殑鍒跺倷鍙婂弽鎳�(y墨ng)娲绘€х殑鍗€(q奴)鍒ヨ垏鍏卞悓榛�(di菐n) 4.3 浜嗚В鐐旂殑鍒跺倷锛岀壒鍒ユ槸涔欑倲鐨勬€ц唱(zh矛)銆佸埗鍌欐柟娉曞強鐢ㄩ€� 绗簲绔� 鑻強鑺抽鐑� 鎺屾彙鑺抽鐑撮鍖栧悎鐗╃殑鍛藉悕鍜岀祼(ji茅)妲�(g貌u)(sp2 闆滃寲)鐗瑰垾鏄嫰鐨� 鐗规€�(鑺抽鎬�)鍙婄祼(ji茅)妲�(g貌u)鐗瑰緛 鎺屾彙鑺崇兇椤炲寲鍚堢墿鐨勯噸瑕佹€ц唱(zh矛)锛氳嫰鍙婂悓鍒嗙墿鐨勫弽鎳�(y墨ng)锛屽彇浠� 鍙嶆噳(y墨ng)鐨勫畾浣嶈(gu墨)寰�銆佸彇浠f晥鎳�(y墨ng)鐨勮В閲嬶紝骞惰兘鎳�(y墨ng)鐢ㄥ湪鏈夋(j墨)鍚堟垚涓�銆� 浜嗚В鑻�銆佺敳鑻�銆佽悩鐨勬€ц唱(zh矛)鍙婇噸瑕佺敤閫�; 5.1 鑺抽鐑� 5.1.1 鐔熸倝鑻殑鍒嗗瓙绲�(ji茅)妲�(g貌u)锛氬嚤搴嫆(Kekule)寮忋€佸垎瀛愯粚閬撴硶銆� 鍏辨尟璜栫啊(ji菐n)浠�锛岃姵棣欐€цВ閲� 5.1.2 浜嗚В鍠挵(hu谩n)鑺抽鐑寸殑鐣版(g貌u)鐝�(xi脿n)璞″拰鍛藉悕 5.1.3 鎺屾彙鑻強鍏跺悓绯荤墿鐨勭墿鐞嗗拰鍖栧(xu茅)鎬ц唱(zh矛) 5.1.3.1 鍙栦唬鍙嶆噳(y墨ng)锛氶沟浠�銆佺鍖栥€佺:鍖�銆佸倕鈥斿厠(Fridel-Crafts) 鍙嶆噳(y墨ng);鑻挵(hu谩n)瑕浕鍙栦唬鍙嶆噳(y墨ng)姝风▼(蟽鈥旂怠(lu貌)鍚堢墿);鑻挵(hu谩n)涓婂彇浠e弽鎳�(y墨ng)鐨� 瀹氫綅瑕�(gu墨)寰�(鐞嗚珫瑙i噵鍜屽悎鎴愪笂鐨勬噳(y墨ng)鐢�)瓒呭叡杌涙晥鎳�(y墨ng)銆� 5.1.3.2 楣电礌(Cl)鐢插熀鍖栧弽鎳�(y墨ng), 5.1.3.3 姘у寲鍙嶆噳(y墨ng)锛氳嫰鐠�(hu谩n)鍋�(c猫)閺堟哀鍖� 5.1.3.4 閲嶈鐨勫柈鐠�(hu谩n)鑺崇兇锛氳嫰銆佺敳鑻€佷簩鐢茶嫰銆佽嫰涔欑儻 5.2 澶氱挵(hu谩n)鍙婄鐠�(hu谩n)鑺崇兇 5.2.1 浜嗚В涓夎嫰鐢插熀鍖栧悎鐗╁強鍏堕洟瀛愬拰鑷敱鍩虹殑绌�(w臎n)瀹氭€� 5.2.2 鎺屾彙钀橈細 绲�(ji茅)妲�(g貌u)鎬ц唱(zh矛)鍙婂叾鍙栦唬鍙嶆噳(y墨ng)銆佸姞鎴愬弽鎳�(y墨ng)銆佹哀鍖� 鍙嶆噳(y墨ng) 5.2.3 浜嗚В钂藉拰鑿诧細绲�(ji茅)妲�(g貌u)鍜屾€ц唱(zh矛)(9銆�10 浣嶇殑娲绘綉鎬�) 5.4 鎺屾彙鑺抽鎬э細浼戝厠鑰�(Huckel)瑕�(gu墨)鍓囧強鍏舵噳(y墨ng)鐢� 绗叚绔� 楣靛寲鐑� 浜嗚В楣典唬鐑寸殑鍒嗛鍜岀墿鐞嗘€ц唱(zh矛) 鎺屾彙楣典唬鐑寸殑鍛藉悕鍙婇噸瑕佸寲瀛�(xu茅)鎬ц唱(zh矛) 鎺屾彙骞剧ó閲嶈鐨勯沟浠g兇鍒跺倷鏂规硶,浜嗚В鍏舵€ц唱(zh矛)銆佸強鎳�(y墨ng)鐢� 6.1 楣典唬鐑寸殑鍒嗛鍙婂懡鍚嶃€佺祼(ji茅)妲�(g貌u)銆佸悓鍒嗙暟妲�(g貌u) 6.2 楣典唬鐑寸殑鐗╃悊鍖栧(xu茅)鎬ц唱(zh矛) 6.2.1 鎺屾彙鍖栧(xu茅)鎬ц唱(zh矛)楣典唬鐑寸殑鍙嶆噳(y墨ng)锛氬彇浠c€佹秷闄�銆侀倓鍘� 6.2.1.1 鍙栦唬鍙嶆噳(y墨ng)锛氭按瑙�銆侀唶瑙�銆佹皑瑙�銆佽垏纭濋吀閵€鍙婃鞍鍖栭垑 鐨勫弽鎳�(y墨ng) 6.2.1.2 娑堝幓鍙嶆噳(y墨ng)锛氭湱渚濆垏澶�(Saytzeff)瑕�(gu墨)鍓� 6.2.1.3 鑸囬噾灞弽鎳�(y墨ng)锛氭牸姘�(Grignard)瑭﹀姂銆佹湁姗�(j墨)閶拌│鍔� 6.2.2 鎺屾彙椋藉拰纰冲師瀛愪笂鐨勮Κ鏍稿彇浠e弽鎳�(y墨ng) 6.2.2.1 鍙栦唬鍙嶆噳(y墨ng)鐨勯洟瀛愭(j墨)鐞� SN1銆丼N2; 娑堥櫎鍙嶆噳(y墨ng)鐨勬(j墨)鐞� E1銆丒2 6.2.2.2 瑕牳鍙栦唬鐨勭珛楂斿寲瀛�(xu茅) 6.2.2.3 鐑村熀绲�(ji茅)妲�(g貌u)銆侀洟鍘诲熀鍦�(tu谩n)灏�(du矛)瑕牳鍙栦唬鍙嶆噳(y墨ng)閫熷害鐨勫奖闊� 6.2.2.4 绲�(ji茅)妲�(g貌u)鑸囧弽鎳�(y墨ng)娲绘€х殑闂�(gu膩n)绯�(鑴傝偑鐑磋垏鑺抽鐑村皪(du矛)姣�,浼徊 鍙斿皪(du矛)姣�) 6.3 鎺屾彙涓€鑸沟浠g兇鐨勫埗娉曪細鐢辩兇鍒跺倷銆佺敱閱囧埗鍌�銆侀沟浠� 鐑寸殑浜掓彌 绗竷绔� 閱�銆侀厷鍜岄啔 鐔熸倝閱�銆侀厷銆侀啔鐨勫垎椤炲拰鍛藉悕鍜岀祼(ji茅)妲�(g貌u)鍚屽垎鐣版(g貌u)(瀹樿兘鍦�(tu谩n)鐣版(g貌u)) 鍜屽厜璀滅壒鎬� 鎺屾彙閱�銆侀厷銆侀啔鐨勯噸瑕佹€ц唱(zh矛)鍜屽弽鎳�(y墨ng)瑕�(gu墨)寰嬶細姘嵉鈥旈唶鑸囬啔灏�(du矛) 姣旈唶鑸囩殑閰氱殑閰告€у皪(du矛)姣�锛岄唶鐨勫弽鎳�(y墨ng)銆侀啔鐨勫弽鎳�(y墨ng)銆佺浠垮弽鎳�(y墨ng)锛岄唶 鐨勯憭鍒ワ細Lucas 瑭﹀姂鍜岄壔閰愮~閰告按娉� 浜嗚В閱囥€侀厷銆侀啔涓噸瑕佺殑鍖栧悎鐗╃殑鎬ц唱(zh矛)銆佸悎鎴愭柟娉曞強鎳�(y墨ng)鐢� 7.1 閱� 7.1.1 閱囩殑鐗╃悊鍜屽寲瀛�(xu茅)鎬ц唱(zh矛) 鐔熸倝鎺屾彙鍏跺寲瀛�(xu茅)鎬ц唱(zh矛)锛氳垏娲绘綉閲戝爆鍙嶆噳(y墨ng)锛岃垏楣靛寲纾�(鎴栦簽纭� 閰版隘)鍙嶆噳(y墨ng)锛岃垏鐒℃(j墨)閰�(姘沟閰�銆佺~閰�銆佺閰�)锛岄叞姘拰閰搁厫绛夌殑 鎴愰叝鍙嶆噳(y墨ng)锛岃劔姘村弽鎳�(y墨ng)锛屾哀鍖栧拰鑴矮鍙嶆噳(y墨ng)锛岀浉閯颁簩閱囩壒鏈夌殑鍙嶆噳(y墨ng) Cu(OH)2銆丠IO4銆佺墖鍚堕唶(pinacol)閲嶆帓銆佺茎鍩鸿缃彌鍙嶆噳(y墨ng)(閯� 鍩哄弮鑸囨晥鎳�(y墨ng)) 7.1.2 鎺屾彙娑堝幓鍙嶆噳(y墨ng)姝风▼ 尾鈥旀秷鍘诲弽鎳�(y墨ng)锛氬弽鎳�(y墨ng)姝风▼ E1銆丒2锛� 娑堥櫎鍙嶆噳(y墨ng)鐨勫彇鍚戯細鏈緷鍒囧か瑕�(gu墨)鍓囩殑瑙i噵锛岃垏瑕牳鍙栦唬鍙嶆噳(y墨ng)鐨勭(j矛ng) 鐖�(zh膿ng) 7.1.3 鎺屾彙閱囩殑鍒舵硶锛氶沟浠g兇姘磋В锛岄啗銆侀叜鐨勯倓鍘�锛岀敱鏍兼皬 瑭﹀姂鍚堟垚锛岀儻鐑寸殑缇ユ睘鍖栥€� 7.2 閰� 7.2.1 鎺屾彙閰氱殑鐗╃悊鎬ц唱(zh矛)銆佸寲瀛�(xu茅)鎬ц唱(zh矛)鍙婂弽鎳�(y墨ng) (1) 閰氱茎鍩虹殑鎬ц唱(zh矛)锛氬急閰告€с€侀厷閱氱殑鐢熸垚銆侀’鑹插弽鎳�(y墨ng)(FeCl3) (2) 鑻挵(hu谩n)涓婅Κ闆诲彇浠e弽鎳�(y墨ng)锛屾哀鍖栧弽鎳�(y墨ng) 7.3 閱� 7.3.1 鎺屾彙閱氱殑鍒舵硶锛� 閱囩殑鑴按锛屽▉寤夊閬�(Williamson) 7.3.2 鎺屾彙閱氱殑鐗╃悊鍖栧(xu茅)鎬ц唱(zh矛)鍙婂弽鎳�(y墨ng)锛氶菇鐨勭敓鎴愩€侀啔閸电殑鏂� 瑁�銆侀亷姘у寲鐗╃殑鐢熸垚 绗叓绔� 閱涖€侀叜椤炵景鍩哄寲鍚堢墿 鎺屾彙閱�銆侀叜鍖栧悎鐗╃殑鍒嗛銆佸懡鍚�銆佺祼(ji茅)妲�(g貌u)鍙婄暟妲�(g貌u)銆佺墿鎬у強鍏� 璀滅壒鎬� 鎺屾彙閱�銆侀叜椤炵景鍩哄寲鍚堢墿鐨勯噸瑕佹€ц唱(zh矛)鍜屽弽鎳�(y墨ng)瑕�(gu墨)寰� 鐔熸倝閲嶈閱涖€侀叜鍖栧悎鐗╃殑鎬ц唱(zh矛)銆佸悎鎴愭柟娉曞拰鎳�(y墨ng)鐢� 8.1 閱涖€侀叜椤炵景鍩哄寲鍚堢墿鐨勭墿鐞嗗寲瀛�(xu茅)鎬ц唱(zh矛) 8.1.1 鐔熸倝骞舵帉鎻¤垏鍚哀銆佸惈纭€佸惈纰�銆佸惈姘Κ鏍歌│鍔戠殑鍔� 鎴愬弽鎳�(y墨ng)鍙婂弽鎳�(y墨ng)姝风▼锛屽姞鎴愨€旀秷鍘诲弽鎳�(y墨ng)姝风▼锛屽奖闊跨景鍩烘椿鎬х殑鍥� 绱狅細鍔� HCN銆丯aHSO3銆丷MgX銆丷OH銆丠2O锛岃垏鏈夋(j墨)鑳哄強 鍏惰鐢熺墿鐨勫姞鎴愮府鍚堝弽鎳�(y墨ng)锛岃垏姘ㄧ殑琛嶇敓鐗╃殑鍙嶆噳(y墨ng)銆� 8.1.2 伪鈥�?d煤)婀擃厫鎷ュ纾�?y墨ng)锛氶沟浠�(楣典豢鍙嶆噳(y墨ng))銆佺茎閱涚府鍚� 8.1.3 鎺屾彙鍏舵哀鍖栭倓鍘熷弽鎳�(y墨ng) a)姘у寲;鎵樺€�(Tollens)瑭﹀姂銆佽不(f猫i)鏋�(Fehling)瑭﹀姂銆佸挤(qi谩ng)姘у寲鍔� b)閭勫師锛欻2, LiAlH4, NaBH4, B2H6, Zn/Hg/H+,NH2NH2/KOH 绛夐倓鍘熸垚閱�(闆欏垎瀛愰倓鍘�)銆侀倓鍘熸垚鐑�銆� 鍏嬮噷闁€閬�(Clemmensen)鍙嶆噳(y墨ng)銆佹鐖惧か鈥旈枊姝囩磵 (Wollf-Kishner)鈥旈粌槌撮緧鍙嶆噳(y墨ng) c)姝у寲锛氬悍灏兼煡缇�(Cannizzaro)鍙嶆噳(y墨ng)銆� 8.1.4 浜嗚В閱涚殑鑷韩鍔犳垚鑱氬拰 8.1.5 浜嗚В閱涚殑椤壊鍙嶆噳(y墨ng)锛氬笇澶�(Schiff)瑭﹂(y脿n) 8.2 鎺屾彙閱涖€侀叜鐨勫埗娉曪細閱囩殑姘у寲銆佺兇鐨勬哀鍖�锛屽仌浜岄沟浠� 鐗╃殑姘磋В锛屽倕鈥斿厠?锛涱姮顕;?y墨ng)锛� 鐐旂兇鐨勭景鍩哄寲锛岀晶閰稿強鍏惰 鐢熺墿鐨勯倓鍘�銆� 8.3 鐔熸倝 伪锛屛测€斾笉椋藉拰閱涢叜鐨勭壒鎬э細1锛�4鈥斿姞鎴�; 绗節绔� 缇ч吀鍙婄晶閰歌鐢熺墿 浜嗚В缇ч吀鍙婂叾琛嶇敓鐗╃殑鍒嗛鍜屽懡鍚� 鎺屾彙缇ч吀鍙婂叾琛嶇敓鐗╃殑閲嶈鎬ц唱(zh矛) 鐔熸倝鎺屾彙涔欓叞涔欓吀涔欓叝鍜屼笝浜岄吀浜屼箼閰湪鏈夋(j墨)鍖栧悎鐗╃殑鎳�(y墨ng) 鐢� 9.1 缇ч吀鐨勫懡鍚�銆佺墿鎬у強鍏夎瓬鐗规€� 9.2 鐔熸倝缇ч吀鐨勭祼(ji茅)妲�(g貌u)鑸囬吀鎬�(瑾樺皫(d菐o)鏁堟噳(y墨ng)锛屽叡杌涙晥鎳�(y墨ng)鍙婂牬(ch菐ng)鏁堟噳(y墨ng) 鐨勫奖闊�) 9.3 鐔熸倝缇ч吀鐨勫埗鍌欙細鐢辩兇銆佷集閱囨垨閱涚殑姘у寲銆佺敱閰埗鍌�銆� 鐢辫厛姘磋В鍙婇噾灞湁姗�(j墨)瑭﹀姂鍚� 鎴愬鏍兼皬瑭﹀姂鍒跺倷 9.4 鎺屾彙缇ч吀鐨勫弽鎳�(y墨ng) 閰告€х晶鍩轰腑姘師瀛愮殑鍙嶆噳(y墨ng)(鍙栦唬鍩哄皪(du矛)閰告€х殑褰遍熆銆佽獦灏�(d菐o)鏁� 鎳�(y墨ng))銆佸舰鎴愰吀楣点€侀叝銆侀叞鑳�銆佽劔缇с€佄扁€擧 鐨勯沟浠e弽鎳�(y墨ng)銆侀倓鍘�(琚� 姘寲閶侀嫲閭勫師)銆侀叝鍖栧弽鎳�(y墨ng)鐨勬(j墨)鐞嗙晶鍩轰腑鐨勭晶鍩虹殑鍙嶆噳(y墨ng)(閰寲鍙� 鎳�(y墨ng)鐨勬绋嬶細闂℃槑姗�(j墨)鐞嗙殑鍚屼綅绱犳硶) 9.5 浜嗚В閲嶈鐨勭晶閰革細鐢查吀銆佷箼閰搞€佷笝鐑吀銆佽嫰鐢查吀銆佽悩 涔欓吀銆� 9.6 鐔熸倝缇ч吀琛嶇敓鐗╅叞楣�銆侀叝銆侀叞鑳恒€佽厛鐨勫垎椤�銆佸懡鍚嶃€� 绲�(ji茅)妲�(g貌u)姣旇純銆佺墿鐞嗗拰鍖栧(xu茅)鎬ц唱(zh矛)銆佸弽鎳�(y墨ng)鍜屽埗鍌�;鎺屾彙缇ч吀琛嶇敓鐗╃殑 鍖栧(xu茅)鍙嶆噳(y墨ng)鍙婂叾鐩镐簰杞�(zhu菐n)鍖栵細瑕牳鍙栦唬鍙嶆噳(y墨ng)(鍔犳垚鈥旀秷鍖栧弽鎳�(y墨ng)姝� 绋�)銆佹按瑙c€侀唶瑙�銆佹皑瑙i叝鐨勬按瑙e強姝风▼;鑸囬噾灞│鍔戠殑鍙嶆噳(y墨ng); 缇ч吀琛嶇敓鐗╃殑閭勫師;閰府鍚堝弽鎳�(y墨ng);閰版皑鐨勮劔姘村拰闇嶅か鏇� (Hofffmann)闄嶈В鍙嶆噳(y墨ng)銆� 9.7 鐔熸倝骞舵帉鎻′箼閰颁箼閰镐箼閰拰涓欎簩閰镐簩涔欓叝鐨勫埗鍌欒垏鎳�(y墨ng) 鐢� a)涔欓叞涔欓吀涔欓叝锛氬埗鍌欍€佷簰璁婄暟妲�(g貌u)鍙婂叾鍦ㄥ悎鎴愪笂鐨勬噳(y墨ng)鐢� b)涓欎簩閰镐簩涔欓叝鍙婂叾鍦ㄥ悎鎴愪笂鐨勬噳(y墨ng)鐢� 9.8 鐔熸倝鍙栦唬缇ч吀(濡傞沟浠i吀銆佺茎閰�銆侀叜閰�)鐨勫悎鎴愯垏鍙嶆噳(y墨ng)锛� 浜嗚В澶氬厓缇ч吀鐨勬€ц唱(zh矛) 绗崄绔� 绔嬮珨鍖栧(xu茅) 10.1 浜嗚В灏�(du矛)鏄犵暟妲�(g貌u)( enantiomers )鐝�(xi脿n)璞�銆佺墿璩�(zh矛)鐨勬棆鍏夋€ц垏 鍒嗗瓙绲�(ji茅)妲�(g貌u)鐨勯棞(gu膩n)绯伙細 10.2 鐔熸倝鍚湁鎵嬫€х⒊鍘熷瓙鍖栧悎鐗╃殑灏�(du矛)鏄犵暟妲�(g貌u) a)鍚湁涓€鍊�(g猫)鎵嬫€х⒊鍘熷瓙鍖栧悎鐗╃殑灏�(du矛)鏄犵暟妲�(g貌u)銆佸皪(du矛)鏄犻珨銆佸娑� 鏃嬮珨銆佽不(f猫i)姝囩埦(Fischer)鎶曞奖寮� b)灏�(du矛)鏄犵暟妲�(g貌u)楂旂殑妲�(g貌u)鍨嬶細鐩稿皪(du矛)妲�(g貌u)鍨嬪拰绲曞皪(du矛)妲�(g貌u)鍨�銆佹帉鎻℃(g貌u)鍨嬬殑 R/S 娉�(娆″簭瑕�(gu墨)鍓�)銆� c)鍚叐鍊�(g猫)鎵嬫€х⒊鍘熷瓙鍖栧悎鐗╃殑灏�(du矛)鏄犵暟妲�(g貌u)锛氶潪灏�(du矛)鏄犻珨銆佸収(n猫i)娑� 鏃嬮珨 10.3 鎺屾彙鐑兇鍖栧悎鐗╃殑骞句綍鐣版(g貌u)楂旓細闋嗗弽鐣版(g貌u)鍙婃€ц唱(zh矛)銆� 10.4 鎺屾彙绔嬮珨鍖栧(xu茅)鍦ㄧ爺绌跺弽鎳�(y墨ng)姝风▼涓殑鎳�(y墨ng)鐢細鐑兇鐨勫姞婧� 绗崄涓€绔� 绱呭锛屾牳纾佸叡鎸瓬鍦栧垎鏋� 鐔熸倝绱呭鍏夎瓬銆佹牳纾佸叡鎸瓬鐨勫熀鏈師鐞嗗強鍦ㄦ湁姗�(j墨)鍖栧悎鐗╃祼(ji茅) 妲�(g貌u)娓�(c猫)瀹氫腑鐨勬噳(y墨ng)鐢� 閬�(d谩)鍒拌兘澶犲埄鐢ㄥ悇绋瓬鍦栫殑缍滃悎淇℃伅骞剁祼(ji茅)鍚堢啊(ji菐n)鍠寲瀛�(xu茅)鍙嶆噳(y墨ng)鍘� 鍒ゆ柗杓冪偤寰�(f霉)闆滅殑鍖栧悎鐗╃殑绲�(ji茅)妲�(g貌u) 11.1 绱呭鍏夎瓬 11.1.1 鍩烘湰鍘熺悊锛氬垎瀛愭尟鍕�(d貌ng)椤炲瀷銆佺磪澶栧厜璀滃湒鐨勮〃绀烘柟娉� 11.1.2 鐔熸倝閲嶈瀹樿兘鍦�(tu谩n)鐨勭壒寰佸惛鏀跺嘲锛屽奖闊跨磪澶栧惛鏀朵俊铏�(h脿o) 浣嶇Щ鐨勫洜绱� 11.1.3 鎺屾彙閲嶈瀹樿兘鍦�(tu谩n)鐨勭磪澶栧厜璀滅壒寰佸強鍏稿瀷绨�(ji菐n)鍠湁姗�(j墨)鍖� 鍚堢墿鐨勭磪澶栧厜璀滃湒鐨勮В閲� 11.2 鏍哥鍏辨尟璀� 11.2.1 浜嗚В鏍哥鍏辨尟鐨勫熀鏈師鐞�,绛夊児(ji脿)璩�(zh矛)瀛愯垏闈炵瓑鍍�(ji脿)璩�(zh矛)瀛�, 鍋跺悎甯告暩(sh霉) 11.2.2 鎺屾彙绨�(ji菐n)鍠吀鍨嬪寲鍚堢墿鐨勬牳纾佸叡鎸瓬鍓栨瀽锛氬睆钄芥晥鎳�(y墨ng) 鍜屽寲瀛�(xu茅)浣嶇Щ锛屽嘲闈㈢⿳鐨勫挤(qi谩ng)搴﹁垏璩�(zh矛)瀛愭暩(sh霉)锛岃嚜鏃嬪伓鍚堣垏鑷棆瑁傚垎 绗崄浜岀珷 鑳哄強鍏朵粬鍚爱鍖栧悎鐗� 鎺屾彙鑳洪鍖栧悎鐗╃殑绲�(ji茅)妲�(g貌u)銆佸垎椤�銆佸懡鍚嶅拰鐗╃悊鍖栧(xu茅)鎬ц唱(zh矛)銆佸弽 鎳�(y墨ng)瑕�(gu墨)寰嬪拰閲嶈鍖栧悎鐗╃殑鎳�(y墨ng)鐢� 鎺屾彙纭濆熀鍖栧悎鐗╃殑绲�(ji茅)妲�(g貌u)銆佸垎椤�銆佸懡鍚嶅拰閲嶈鐨勫寲瀛�(xu茅)鎬ц唱(zh矛) 12.1 鑳虹殑鍒嗛銆佸懡鍚�銆佺祼(ji茅)妲�(g貌u)鐗╂€у拰鍏夎瓬鐗瑰緛 12.2 鐔熸倝骞舵帉鎻¤兒鐨勬€ц唱(zh矛)鐗╃悊鍜屽寲瀛�(xu茅)鎬ц唱(zh矛) 12. 2. 1 鑳虹殑绲�(ji茅)妲�(g貌u)鍜屽牽鎬�(绲�(ji茅)妲�(g貌u)鐗归粸(di菐n)銆佹墜鎬�銆佸牽鎬у強褰遍熆鍫� 鎬уぇ灏忕殑鍥犵礌) 12. 2. 2 鎴愰菇銆佸洓绱�(j铆)閵ㄩ菇鐨勫舰鎴愩€佺壒榛�(di菐n)鍙婃噳(y墨ng)鐢�(寰瑰簳鐢插熀鍖� 鍙嶆噳(y墨ng)銆佸洓绱�(j铆)閵ㄥ牽鐨勫舰鎴�锛岀浉杞�(zhu菐n)绉诲偓鍖栧姂)銆丠ofmann 娑堥櫎(瑕�(gu墨)寰嬨€� 鍙嶆噳(y墨ng)姗�(j墨)鐞�) 12.2.3 ?锛涱姮顕橀槀闃�锛涱嚃鈪わ經u銆侀吀閰愩€佽嫰纾洪叞姘�(鑸堟柉鍫� Hinsberg 鍙嶆噳(y墨ng)) 12.2.4 鑳虹殑姘у寲鍜� Cope 娑堥櫎(闋嗗瀷娑堥櫎) 12.2.5 鑳鸿垏浜炵閰哥殑鍙嶆噳(y墨ng)(閲嶆爱鍖栧弽鎳�(y墨ng)) 12.2.6 鑳虹殑鐗规畩鍙嶆噳(y墨ng)锛氭槗姘у寲銆佽嫰鐠�(hu谩n)涓婃槗鍙栦唬; Mannich 鍙嶆噳(y墨ng)鍙婂叾鎳�(y墨ng)鐢� 12.3 鐔熸倝鎺屾彙鑳虹殑鍒跺倷锛氭皑鎴栬兒鐨勭兇鍩哄寲銆佽姵楣电殑姘ㄨВ(鑻� 鐐�); 钃嬪竷鐟炵埦(Gabriei)鍚堟垚娉�锛岀敤閱囧埗鍌�锛屽惈姘寲鍚堢墿鐨勯倓鍘�: 纭濆熀鍖栧悎鐗╃殑閭勫師, 鑵�銆侀叞鑳�銆佽偀鐨勯倓鍘�; 寰炵晶閰稿強鍏惰鐢熺墿 鍒跺倷( 闇嶅か鏇奸噸鎺�) 12.4 鎺屾彙閲嶆爱鍜屽伓姘寲鍚堢墿锛氶噸姘敳鐑峰強鍗¤硴銆佹爱鐑�銆佺枈 姘寲鐗╃殑鍒跺倷銆佸弽鎳�(y墨ng) 12.5.1 閲嶆爱楣界殑鍒舵硶 12.5.2 閲嶆爱楣界殑鎬ц唱(zh矛)锛氬幓姘弽鎳�(y墨ng)(琚€擧銆丱H銆佲€擷銆佲€擟N 鍙栦唬)銆佺暀姘弽鎳�(y墨ng)(鍋跺悎鍜岄倓鍘�) 12.6 纭濆熀鍖栧悎鐗� 12.6.1 浜嗚В鍒嗛銆佺祼(ji茅)妲�(g貌u)鍜屽懡鍚� 12.6.2 鎺屾彙鍏舵€ц唱(zh矛)锛氱鍩哄皪(du矛) 伪鈥�?d煤)婀擃厫鎷ユ尃缁�?浜掕畩鐣版(g貌u)) 閭勫師銆佺鍩哄皪(du矛)鑻挵(hu谩n)涓婂彇浠e熀鐨勫奖闊� 12.6.3 鐔熸倝閲嶈鐨勭鍩哄寲鍚堢墿锛氱鍩鸿嫰銆佽嫤鍛抽吀銆乀NT 12.8 鎺屾彙鍚爱鑺抽鍖栧悎鐗╃殑浠ヤ笅鏈夐棞(gu膩n)鍏�(n猫i)瀹� 12.8.1 鑺抽纭濆熀鍖栧悎鐗╃殑绲�(ji茅)妲�(g貌u)銆佺墿鐞嗗強鍖栧(xu茅)鎬ц唱(zh矛) 12.8.2 鑺宠兒鐨勫埗鍌欏拰鑺宠兒鐨勭壒鎬� 12.8.3 鑻倲鐨勫埗鍌欏拰鐠�(hu谩n)鍔犳垚鍙嶆噳(y墨ng) 12.8.4 鑺宠兒鐨勯噸姘菇鍙婂弽鎳�(y墨ng)鍙婂叾鍦ㄥ悎鎴愪笂鐨勬噳(y墨ng)鐢� 绗崄涓夌珷 鍚~銆佺7銆佺鍖栧悎鐗� 鐔熸倝鍚~鍖栧悎鐗╃殑鍖栧(xu茅)鎬ц唱(zh矛)锛屼簡瑙e叾鐗╃悊鎬ц唱(zh矛) 鐔熸倝鏈夋(j墨)纾峰寲鍚堢墿鐨勫垎椤�銆佸懡鍚嶄互鍙婃湁姗�(j墨)纾疯静(n贸ng)钘ョ殑鎬ц唱(zh矛)銆� 鎬ц兘鍜屾噳(y墨ng)鐢� 浜嗚В鍚鍖栧悎鐗╃殑鐗╃悊鎬ц唱(zh矛)鍙婂寲瀛�(xu茅)鎬ц唱(zh矛) 13.1 纭�銆佺7鍏冪礌鍘熷瓙鐨勯浕瀛愭(g貌u)鍨嬪拰鎴愰嵉鐗瑰緛 13.2 鐔熸倝鍚~鍖栧悎鐗╃殑绲�(ji茅)妲�(g貌u)椤炲瀷鍜屽懡鍚嶅強鍚堟垚鑸囧弽鎳�(y墨ng) 纭唶鍜岀~閰�銆佺~閱氥€佷簽鐮滃拰鐮�銆佺:閰稿強鍏惰鐢熺墿(纾鸿兒钘ョ墿銆� 绯栫簿) 绗崄鍥涚珷 绺悎鍙嶆噳(y墨ng)(鐔熸倝鍜屾帉鎻″ぇ閮ㄥ垎鍏�(n猫i)瀹�) 14.1 閱�銆侀啗鍨嬬府鍚堝弽鎳�(y墨ng)锛氭豢灏艰但鈥旇兒鐢插熀鍖栧弽鎳�(y墨ng)銆侀亥鍏嬬埦 鍔犳垚銆侀璩撻仠澧炵挵(hu谩n)鍙嶆噳(y墨ng) 14.2 閰殑閰板熀鍖栧弽鎳�(y墨ng)锛氶叝绺悎鍙嶆噳(y墨ng)(鍏嬭悐妫府鍚堝弽鎳�(y墨ng)銆佹贩 鍚堥叝绺悎銆佸垎瀛愬収(n猫i)鐨勯叝 绺悎鍙嶆噳(y墨ng)(鐙勫厠鏇肩府鍚堝弽鎳�(y墨ng))銆佺敤閰版隘鎴栭吀閰愰€�(j矛n)琛�?锛涱姮?br/>14.3 閰殑鐑峰熀鍖栥€�?锛涱姮顕;?y墨ng)銆佺稉(j墨ng)鐑兒鐑峰熀鍖栨垨?锛涱姮?br/>14.4 尾-浜岀景鍩哄寲鍚堢墿鐨勭壒鎬у強鍦ㄥ悎鎴愪笂鐨勬噳(y墨ng)鐢細尾-浜岀晶鍩� 鍖栧悎鐗╃殑鐗规€� 銆佷笝浜岄吀閰悎鎴愭硶銆佷箼閰颁箼閰镐箼閰悎鎴愭硶銆�1,3- 浜岀晶鍩哄寲鍚堢墿鐨� 纬-鐑峰熀鍖栧拰 纬-?锛涱姮?銆侀叝绺悎鐨勯€嗗悜鍙嶆噳(y墨ng) 14.5 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