{"id":10916,"date":"2020-10-13T12:29:07","date_gmt":"2020-10-13T06:59:07","guid":{"rendered":"http:\/\/astan.lk\/al_virtualclassroom\/?p=10916"},"modified":"2020-10-13T12:30:01","modified_gmt":"2020-10-13T07:00:01","slug":"directing-ability-substituent-groups","status":"publish","type":"post","link":"https:\/\/astan.lk\/al_virtualclassroom\/directing-ability-substituent-groups\/","title":{"rendered":"The directing ability of substituent groups"},"content":{"rendered":"
\n

Examples of activating groups in the relative order from the most activating group to the least activating:<\/p>\n

-NH2<\/sub>, -NR2<\/sub> > -OH, -OR>\u00a0\u00a0-NHCOR> -CH3<\/sub>\u00a0and other alkyl groups<\/p>\n

with R as alkyl groups (Cn<\/sub>H2n<\/sub>+1<\/sub>)<\/p>\n

Examples of deactivating groups in the relative order from the most deactivating to the least deactivating:<\/p>\n

-NO2<\/sub>, -CF3<\/sub>> -COR, -CN, -CO2<\/sub>R, -SO3<\/sub>H > Halogens<\/p>\n

with R as alkyl groups (Cn<\/sub>H2n<\/sub>+1<\/sub>)<\/p>\n

The order of reactivity among Halogens from the more reactive (least deactivating substituent) to the least reactive\u00a0(most deactivating substituent) halogen is:<\/p>\n

F> Cl > Br > I<\/p>\n

The order of reactivity of the benzene rings toward the electrophilic substitution when it is substituted with a halogen groups, follows the order of electronegativity. The ring that is\u00a0substituted with\u00a0the most electronegative halogen is\u00a0the most reactive ring ( less deactivating substituent\u00a0) and the ring that is substituted with the least electronegatvie halogen is the least reactive\u00a0ring ( more deactivating substituent ), when we compare rings with halogen substituents. Also the size of the halogen\u00a0effects the reactivity of the benzene ring that the halogen is attached to. As the size of the halogen increase, the reactivity of\u00a0the ring\u00a0decreases.<\/p>\n<\/div>\n

<\/span><\/p>\n

The direction of the reaction<\/h3>\n

The activating group directs the reaction to the ortho or para position, which means the electrophile substitute the hydrogen that is on carbon 2 or carbon 4. The deactivating group directs the reaction to the meta position, which means the electrophile substitute the hydrogen that is on carbon 3 with the exception of the halogens that is a deactivating group but directs the ortho or para substitution.<\/p>\n

\"noname1.gif\"\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\"noname2.gif\"\n<\/div>\n

<\/span><\/p>\n

Substituents determine the reaction direction by resonance or inductive effect<\/h3>\n

Resonance effect is the conjugation between the ring and the substituent, which means the delocalizing of the \u03c0<\/span><\/span><\/span>\u03c0<\/span><\/span> electrons between the ring and the substituent. Inductive effect is the withdraw of the\u00a0sigma ( the single bond )\u00a0electrons away from the ring toward the substituent, due to the higher electronegativity of the substituent\u00a0\u00a0compared to the carbon of the ring.<\/p>\n

<\/span><\/p>\n

Activating groups (ortho or para directors)<\/h4>\n

When the substituents like -OH have an unshared pair of electrons, the resonance effect is stronger than the inductive effect which make these substituents stronger activators, since this resonance effect direct the electron toward the ring. In cases where the subtituents is esters or amides, they are less activating because they form resonance structure that pull the electron density away from the ring.<\/p>\n

 <\/p>\n

\"mechanism<\/p>\n

By looking at the mechanism above, we can see how groups donating electron direct the ortho, para electrophilic substition. Since the electrons locatinn transfer between the ortho and\u00a0para carbons, then the electrophile prefer attacking the carbon that has the\u00a0free electron.<\/p>\n

Inductive effect of alkyl groups<\/a> activates the direction of the ortho or para substitution, which is when s\u00a0electrons gets pushed toward the ring.<\/p>\n<\/div>\n

<\/span><\/p>\n

Deactivating group (meta directors)<\/h4>\n

The deactivating groups deactivate the ring by the inductive effect in the presence of an electronegative atom that withdraws the electrons away from the ring.<\/p>\n

\"mechanism<\/p>\n

we can see from the mechanism above that when there is an electron withdraw from the ring, that leaves the carbons at the ortho, para positions with a positive charge which is unfavorable for the electrophile, so the electrophile attacks the carbon at the meta positions.<\/p>\n

Halogens are an exception of the deactivating group that directs the ortho or para substitution. The halogens deactivate the ring by inductive effect not by the resonance even though they have an unpaired pair of electrons. The unpaired pair of electrons\u00a0gets donated to the ring,\u00a0but\u00a0the inductive effect pulls\u00a0away the\u00a0s\u00a0<\/span>electrons from the ring\u00a0by the electronegativity\u00a0of the halogens.<\/p>\n<\/div>\n<\/div>\n

<\/span><\/p>\n

Substituents determine the reactivity of rings<\/h3>\n

The reaction of a substituted ring with an activating group is faster than benzene. On the other hand, a substituted ring with a deactivated group is slower than benzene.<\/p>\n

Activating groups speed up the reaction because of\u00a0the resonance effect. The presence of the unpaired electrons that can be donated to the ring, stabilize the carbocation in the transition state. Thus; stabilizing the intermediate step, speeds up the reaction; and this is due to the decrease of the activating energy. On the other hand, the deactivating groups, withdraw the electrons away from the carbocation formed in the intermediate step, thus; the activation energy is increased which slows down the reaction.<\/p>\n<\/div>\n

<\/span><\/p>\n

The CH3<\/sub>Group is and ortho, para Director<\/h3>\n

\"\"<\/p>\n

Alkyl groups are Inductive activators<\/p>\n

With o\/p attack the form a tertiary arenium carbocation which speeds up the reaction<\/p>\n

\"\"<\/p>\n

\"\"<\/p>\n

\"\"<\/p>\n<\/div>\n

<\/span><\/p>\n

The O-CH3<\/sub> Group is an ortho, para Director<\/h3>\n

 <\/p>\n

\"\"<\/p>\n

Ortho and Para producst produces a resonance structure which stabilizes the arenium ion. This causes the ortho and para products for form faster than meta. Generally, the para product is preferred because of steric effects.<\/p>\n

\"\"<\/p>\n

\"\"<\/p>\n

\"\"<\/p>\n

 <\/p>\n<\/div>\n

<\/span><\/p>\n

Acyl groups are meta Directors<\/h3>\n

 <\/p>\n

\"\"<\/p>\n

Acyl groups are resonance deactivators.\u00a0 Ortho and para attack produces a resonance structure which places the arenium cation next to and additional cation. This destabilizes the arenium cation and slows down ortho and para reaction.\u00a0 By default the meta product forms faster because it lacks this destablizing resonance structure.<\/p>\n

\"\"<\/p>\n

\"\"<\/p>\n

\"\"<\/p>\n<\/div>\n","protected":false},"excerpt":{"rendered":"

Examples of activating groups in the relative order from the most activating group to the least activating: -NH2, -NR2 > -OH, -OR>\u00a0\u00a0-NHCOR> -CH3\u00a0and other alkyl groups with R as alkyl groups (CnH2n+1) Examples of deactivating groups in the relative order from the most deactivating to the least deactivating: -NO2, -CF3> -COR, -CN, -CO2R, -SO3H > […]<\/p>\n","protected":false},"author":842,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"_monsterinsights_skip_tracking":false,"_monsterinsights_sitenote_active":false,"_monsterinsights_sitenote_note":"","_monsterinsights_sitenote_category":0,"footnotes":""},"categories":[14,1666],"tags":[],"class_list":["post-10916","post","type-post","status-publish","format-standard","hentry","category-chemistry","category-unit-08"],"acf":[],"yoast_head":"\nThe directing ability of substituent groups - Learning & Education Portal<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/astan.lk\/al_virtualclassroom\/directing-ability-substituent-groups\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"The directing ability of substituent groups - Learning & Education Portal\" \/>\n<meta property=\"og:description\" content=\"Examples of activating groups in the relative order from the most activating group to the least activating: -NH2, -NR2 > -OH, -OR>\u00a0\u00a0-NHCOR> -CH3\u00a0and other alkyl groups with R as alkyl groups (CnH2n+1) Examples of deactivating groups in the relative order from the most deactivating to the least deactivating: -NO2, -CF3> -COR, -CN, -CO2R, -SO3H > […]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/astan.lk\/al_virtualclassroom\/directing-ability-substituent-groups\/\" \/>\n<meta property=\"og:site_name\" content=\"Learning & Education Portal\" \/>\n<meta property=\"article:published_time\" content=\"2020-10-13T06:59:07+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2020-10-13T07:00:01+00:00\" \/>\n<meta property=\"og:image\" content=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2345\/noname1.gif?revision=1\" \/>\n<meta name=\"author\" content=\"Admin\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"Admin\" \/>\n\t<meta name=\"twitter:label2\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"4 minutes\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\/\/schema.org\",\"@graph\":[{\"@type\":\"Article\",\"@id\":\"https:\/\/astan.lk\/al_virtualclassroom\/directing-ability-substituent-groups\/#article\",\"isPartOf\":{\"@id\":\"https:\/\/astan.lk\/al_virtualclassroom\/directing-ability-substituent-groups\/\"},\"author\":{\"name\":\"Admin\",\"@id\":\"https:\/\/astan.lk\/al_virtualclassroom\/#\/schema\/person\/ffb0504e2cfb71518790b2fffd668c59\"},\"headline\":\"The directing ability of substituent groups\",\"datePublished\":\"2020-10-13T06:59:07+00:00\",\"dateModified\":\"2020-10-13T07:00:01+00:00\",\"mainEntityOfPage\":{\"@id\":\"https:\/\/astan.lk\/al_virtualclassroom\/directing-ability-substituent-groups\/\"},\"wordCount\":863,\"commentCount\":0,\"publisher\":{\"@id\":\"https:\/\/astan.lk\/al_virtualclassroom\/#organization\"},\"image\":{\"@id\":\"https:\/\/astan.lk\/al_virtualclassroom\/directing-ability-substituent-groups\/#primaryimage\"},\"thumbnailUrl\":\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/2345\/noname1.gif?revision=1\",\"articleSection\":[\"Chemistry\",\"Unit 08\"],\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"CommentAction\",\"name\":\"Comment\",\"target\":[\"https:\/\/astan.lk\/al_virtualclassroom\/directing-ability-substituent-groups\/#respond\"]}]},{\"@type\":\"WebPage\",\"@id\":\"https:\/\/astan.lk\/al_virtualclassroom\/directing-ability-substituent-groups\/\",\"url\":\"https:\/\/astan.lk\/al_virtualclassroom\/directing-ability-substituent-groups\/\",\"name\":\"The directing ability of substituent groups - 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