Acid catalyzed reactions you should be able to write arrow-pushing mechanisms for.

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1 Acid catalyzed reactions you should be able to write arrow-pushing mechanisms for. 3 S (- 2 ) S (- 2 ) S (- 2 ) 2 S S 4 2 (both ways) Ts (- 2 ) 2 S 4 / 2 Ts (- 2 ) Ts 1 (TP) 2 S S 4 / 2 2 S S S S S S 4 2 (both ways) 2 2 ketones & aldehydes = or pyrrolidine Ts 3 Ts Ts (- 2 ) 2 S 4 / 2 p 5 Ts (- 2 ) 2 S 4 / 2 3 p 5 Ts (- 2 ) 2 S 4 / 2 imines enamines 3 Z:\classes\316\rganic mechanisms overview\316 arrow pushing practice.doc

2 Examples of acyl substitution reactions, you should be able to write arrow-pushing mechanisms for. 2 l l S S l l 3 riedel-rafts reactions l l l l l u (cuprates) 1. (DIBA) 2. WK undesired side rxn. l 3 riedel-rafts reactions B a 1. (DIBA) 2. WK 2 eqs WK (Grignard reagents too) WK a very slow reaction WK a Z:\classes\316\rganic mechanisms overview\316 arrow pushing practice.doc

3 eaction Mechanism Worksheet Guidelines 3 1. Factors to consider when looking at reactants, reaction intermediates and product(s). a. Are there any resonance effects? b. Are there any inductive effects? c. Are there any steric effects? d. Are there any stereochemical considerations? 2. Where are the pairs of electrons that can be donated? (nucleophilic sites) 3. Which site(s) can accept a pair of electrons? (electrophilic sites) 4. Is the reaction in acid? (A Lewis or onsted acid = E+ = strong, the acidity drives the reaction) a. Usually use a strong acid to supply protons, often the strong acid is the protonated solvent. ( 2 + ), (nonproton Lewis acids can also be species with an empty valency such as B 3, BF 3, l 3, Fe 3, Til 4, SbF 5, etc. which all complex very well with lone pairs.) b. There are no strong electron pair donors in strong acid (bases or nucleophiles are weak). ften the weak base or leaving group is the neutral solvent. () 5. Is the reaction in base? (The strong base/nucleophile drives the reaction.) a. Usually use a weak acid to supply protons, usually the neutral solvent, (), or other neutral molecule of similar acidity. b. Usually an anion (often the conjugate base of the solvent) acts as the strong nucleophile, strong base or good leaving group ( -- ) 6. Are free radicals or one electron transfers involved? ften a photon or neutral (or reduced) metallic compound is part of the reaction. xygen or a peroxide can also serve as a free radical initiator. In mechanism problems of our course include the following. 1. Show all lone pairs of electrons 2. Show all formal charge, when present 3. When resonance is a factor in the stability of an intermediate, draw at least one additional resonance structure, including the best resonance structure. 4. Show all curved arrows to show the flow of electrons (full headed arrow = 2 electron movement) 5. Any free radical centers if present (half headed/fish hook arrow = 1 electron movement) Z:\classes\316\rganic mechanisms overview\316 arrow pushing practice.doc

4 4 Z:\classes\316\rganic mechanisms overview\316 arrow pushing practice.doc Mechanism for Fischer synthesis of ester - as catalytic toluene sulfonic acid with removal of water to shift equilibrium to right. tosylsulfonic acid = Ts- Ts Ts Mechanism for hydrolysis of ester in acid - as catalytic sulfuric acid in large excess of water to shift equilibrium to the right. 2 S 4 : aqueous sulfuric acid (and lots of water) S 3 S 3 carboxylic acid alcohol ester

5 Mechanism for hydrolysis of ester in base (also called saponification) Aqueous sodium hydroxide (a). 5 ester 2. workup carboxylic acid alcohol Protecting dehydes and Ketones as acetals and ketals with ethylene glycol ( and deprotection) Possible mechanism for synthesis of ketal - atalytic toluene sulfonic acid with removal of water to shift equilibrium to right. ketone Ts Ts ethylene glycol remove 2 Ts hemiketal ketal Z:\classes\316\rganic mechanisms overview\316 arrow pushing practice.doc

6 Possible mechanism for hydrolysis of ketal or acetal = addition of water with catalytic amount of sulfuric acid. 6 ketal (water added) ketone ethylene glycol Imine Formation from dehyde or Ketone eaction with Primary Amines - 2 derivatives (primary amines and hydrazine) 1. Follow by reduction with sodium cyanoborohydride (a 3 B) to form 1 o, 2 o and 3 o amines, or Step 1 - making an imine carbonyl group primary amine acid cat. = Ts (remove water) Ts Ts Ts 2 (remove) Ts imine Step 2 - reducing an imine to an amine with sodium cyanoborohydride a 2 B B imine sodium cyanoborohydride (reduces imines to amines) secondary amine Z:\classes\316\rganic mechanisms overview\316 arrow pushing practice.doc

7 7 Z:\classes\316\rganic mechanisms overview\316 arrow pushing practice.doc Possible ydrolysis Mechanism of an imine (if not reduced to an amine) = addition of water with catalytic amount of sulfuric acid. primary amine carbonyl group imine Possible Mechanism for reaction of hydrazine 2 2 with aldehydes and ketones in strong base leading to reduction to a methylene group ( 2 ) = Wolff Kishner eduction. 2 primary amine carbonyl group 2 2

8 Possible Enamine Mechanism Secondary amine plus carbonyl compound with removal of water (we ll always use pyrrolidine). 8 carbonyl group pyrrolidine acid cat. = Ts (remove water) Ts (remove water) enamine Possible Mechanism of Enamine with an Electrophile, (allyl bromide used in this example), Followed by hydrolysis of imminium ion back to a carbonyl compound. 2 enamine alkylated ketone resonance Z:\classes\316\rganic mechanisms overview\316 arrow pushing practice.doc

9 Wittig eaction (pronounce Vittig ) 9 1. Form Wittig salt with triphenylphosphine S 2 reaction on an X compound. 2. Use a strong base to remove a proton from the carbon alpha to the phosphorous atom and 3. Add a carbonyl compound (aldehyde or ketone) which undergoes an addition / elimination reaction to alkenes (we ll assume usually Z stereochemistry). Possible Mechanistic steps for preparation and reaction of a Wittig reagent. 1. Make the Wittig salt. P triphenylphosphine X compound S 2 reaction P Wittig salt 2. Make the ylid. P Wittig salt 3 2 n-butyl lithium acid/base proton transfer P P 3 ylid and its resonance structure 3 3. eact the ylid with a carbonyl compound. 3 P 3 P P dipolar ylid 3 dehydes and ketones react. 3 2 intermediate "betaine" intermediate "oxaphosphatane" 3 P triphenylphosphine oxide Usually the Z alkene is the major product. Z:\classes\316\rganic mechanisms overview\316 arrow pushing practice.doc

10 ucleophilic hydride reactions: with organic electrophiles such as: aldehydes, ketones, esters, epoxides, nitriles and X compounds. ommon forms of nucleophilic hydride used in this course. (emember a is always basic in our course.) 10 a a A B B thium aluminium hydride, 4, (LA, very reactive, reduces many functional groups in our course, including aldehydes, ketones, esters, epoxides, nitriles and X compounds.) Sodium borohydride, ab 4 (somewhat reactive, reduces aldehydes, ketones, epoxides, and X compounds) Sodium cyanoborohydride, ab 3 (used to reduce imines to amines in a reaction similar to the reduction of aldehydes by sodium borohydride). Diisobutylaluminiumhydride, DIBA (or DIBAL), used to diliver a single hydride to esters, nitriles and acid chlorides which become aldehydes after the workup hydrolysis step. This hydride is different from the others in that it is neutral and only has a single hydride nucleophile. ydride nucleophiles (e- pair donors) + organic electrophiles (e- pair acceptors), WK = work up = acidic neutralization (electrophilic hydrogen ). a. formaldehyde (methanal) = reduced to methanol 2. workup ab 4 works too. 2 b. general aldehydes = reduced to primary alcohols (like an ester or carboxylic acid with LA) 2. workup ab 4 works too. 2 primary alcohols d. general ketones = reduced to secondary alcohols B 2. workup 4 works too. 2 secondary alcohols Z:\classes\316\rganic mechanisms overview\316 arrow pushing practice.doc

11 e. general esters = reduced to primary alcohols only with LA (like the aldehyde or a carboxylic acid) workup 2 Two equivalents of nucleophilic hydride add to the ester carbonyl carbon. ne equivalent of electrophilic hydrogen (acid) adds at the oxygen atom. nly LA will reduce esters at a practical rate under normal conditions. primary alcohols f. general carboxylic acid = reduced to primary alcohol (like the aldehyde or ester) 3 primary alcohols 2. workup 2 3 g. ethylene oxide (epoxides) = reduced to ethanol a a 2 B 2 2. workup 2 f. imines (made from primary amine and ketone or aldehyde) reduced to amines with sodium cyanoborohydride a B 2 B imine sodium cyanoborohydride (reduces imines to amines) secondary amine Z:\classes\316\rganic mechanisms overview\316 arrow pushing practice.doc

12 12 Z:\classes\316\rganic mechanisms overview\316 arrow pushing practice.doc B a sodium cyanoborohydride (reduces imines to amines) iminium ion tertiary amine 2 B g. nitriles reduced to 1 o amines with 1. 4, 2. workup. primary amine X X X 2. workup X X X X X X (neutralize) nitrile h. esters and nitriles = reduced to aldehydes with diisobutylaluminium hydride, DIBAL (text = DIBA) nitrile aldehyde

13 i. hydrolysis of nitriles in l/1 eq 2 to amides 13 j. hydrolysis of nitriles in 2 S 4 /excess 2 to carboxylic acids k. hydrolysis of nitriles in a/ 2 to carboxylic acids Z:\classes\316\rganic mechanisms overview\316 arrow pushing practice.doc

14 Possible Mechanism for some of the cuprate reactions Supply all necessary mechanistic details, including lone pairs, formal charge and curved arrows to show electron movement. a. Formation of dialkyl lithium cuprate 14 2 equivalents organolithium reagent u 1 eq. u A transmetallation allows the more electronegative anion () to pair up with the more electropositive cation (), producing a better salt. The less electronegative anion () then pairs up with the less electropositive cation (u) to produce a better covalent bond. u u dialkyllithium cuprate b. onjugate addition to α,β-unsaturated carbonyl u u 2. WK c. Acyl substitution with an acid chloride l u l u l d. oupling reaction with an X compound The ketone is LESS reactive than the acid chloride and does not react further with a cuprate reagent. (It would react further with an organolithium reagent.) u u This reaction can be viewed as an S 2 reaction, but free radicals are likely involved. thium and magnesium reagents produce a lot of side reactions that make this coupling poor for them. 2 "" groups are coupled together with both coming from X compounds. Z:\classes\316\rganic mechanisms overview\316 arrow pushing practice.doc

15 Possible Mechanism for Formation of rganometallics Supply all necessary mechanistic details, including lone pairs, formal charge and curved arrows to show electron movement. Grignard () reagents carbanion nucleophile 2 15 thium reagents carbanion nucleophile Possible Mechanism for eaction of rganometallics with typical rganic Electrophiles Supply all necessary mechanistic details, including lone pairs, formal charge and curved arrows to show electron movement. () carbanion nucleophile methanal +2 1 o alcohol () +2 ' ' aldehydes ' 2 o alcohol ' ' () +2 " " ketones ' " 3 o alcohol () epoxides +2 it depends Z:\classes\316\rganic mechanisms overview\316 arrow pushing practice.doc

16 () +2 carbon dioxide carboxylic acid 16 ' ' +2 () " " esters Esters react twice with organomagnesium and lithium reagents, since the initially formed intermediate collapses back to a ketone, which is more reactive than the initially attacked ester, and gets attacked a second time. ' ' ' () () " carbanion nucleophile methanal 1 o alcohol carbanion nucleophile methanal 1 o alcohol carbanion nucleophile methanal 1 o alcohol ' aldehydes ' ' 2 o alcohol Z:\classes\316\rganic mechanisms overview\316 arrow pushing practice.doc

17 17 ' " ketones ' " ' " 3 o alcohol epoxides it depends carbon dioxide carboxylic acid ' " esters ' " ' " Esters react twice with organomagnesium and lithium reagents, since the initially formed intermediate collapses back to a ketone, which is more reactive than the initially attacked ester, and gets attacked a second time. ' ' This is the one difference between (Grignard) and reagents in our course. The lithium organometallics are a bit more reactive and will add to even a carboxylate, which after workup hydrolyze to a ketone. This takes the addition of three protons. ' carboxylic acid ' second equivalent ' ' ' ' ' ' ' Z:\classes\316\rganic mechanisms overview\316 arrow pushing practice.doc

18 xidation of alcohols with chromium reagents (P, Jones,there are others too ) 18 verall eactions a. P reagent b. Jones reagent methyl alcohol 3 r 3 / methyl alcohol 3 r 3 / primary alcohol r 3 / primary alcohol r 3 / secondary alcohol r 3 / secondary alcohol r 3 / tertiary alcohol tertiary alcohol r 3 / o eaction r 3 / o eaction Possible xidation Mechanism all viewed as r 3 (either without water present or with water present). Supply all necessary mechanistic details, including lone pairs, formal charge and curved arrows to show electron movement. a. P - without water present no carbonyl hydrate forms primary alcohol r r = +6 r 3 / P conditions (no water) r r aldehyde r r = +4 Z:\classes\316\rganic mechanisms overview\316 arrow pushing practice.doc

19 19 ' secondary alcohol r r = +6 r 3 / P conditions (no water) r ' r ' ' ketone r r = +4 P with water Possible ydration Mechanism, followed by oxidation of the carbonyl hydrate (Jones reaction). aldehyde from first r oxidation carbonyl r hydrate r = +6 carboxylic acid r r = +4 r r That s all I could do for now. Try some keto/enol mechanisms in acid and in base. Z:\classes\316\rganic mechanisms overview\316 arrow pushing practice.doc

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