#rmgx

[tenth-sentence]

It is important to realise that it is not possible to use RMgX and an ester to prepare an anhydride or a ketone; the intermediate aldehyde or ketone is more reactive than the ester and reacts immediately with the Grignard reagent to give an alcohol.

"Chemistry" 2e - Blackman, A., Bottle, S., Schmid, S., Mocerino, M., Wille, U.

[stellardigital]

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[goodvibesandchemnotes]

I've got a few comments on this image.

This is pretty much spot on perfect. My only correction is the first two cols are more "useful, boring counterions" or "disturbingly strong reducing agents", halogens are extremely useful but all vaguely the same thing with varying oxidizing strength/softness. Group 1 (alkali) and 17 (halogen) are often lumped together as just M and X respectively, with increasing ionic strength and size varying for M.

I guess carbon's missing neighbors are pretty important still, Boron and silicon aren't just catalysts but aren't the normal heteroatoms NOPS. They're more like "NOPS, but only used as stable reaction intermediates", like I'm not gonna find phenylboronic acid in the wild nor in an over the counter product but I am ABSOLUTELY gonna have shelf stable phenylboronic acid in the lab for a Suzuki coupling or an anti-markovnikov oxidation. Or borohydride is the BEST reducing agent, ranging from BH4 for the strongest, to HB(OAc)3 or H3BCN. Aluminum hydrides are comparable but stronger, although you won't really find organoalanes just sitting on the shelf. Aluminum kinda falls into the catalyst only area outside of LiAlH4.

Or, organosilicon chemistry is something I poke fun at often because it's FAR more like organotin or organolead than classic organics, just without the electronegativity difference of carbon group metals. But aside from organic silicones like poly(dimethylsiloxane), trimethylsilyl [Si(CH3)3 or TMS] groups are indispensable when you need something that's bulky, relatively easy to move around while still being mostly inert.

Heavy pnictogens (As, Sb, Bi) and chalcogens (Se, Te) are pretty similar to their parent P and S (the periodic table starts at period 3 imo, only period 2 cares about the octet rule), just more toxic, more stinky, and generally more useless. Organoarsenic was the first ever branch of "organometallics" but hasn't been relevant in over a century.

The d block is all random catalysts and the f block is nearly useless tho that's nearly SPOT on. Cu, Zn, Hg, Pd, Pt are all useful but in the "$" category. It feels like it takes as long to learn each transition metal's uses as it does to learn all of organic 1, they just break the rules and I won't go into organometallics right now I promise (even though I'm foaming at the mouth over ferrocene two years later)

Actually I've literally never seen a group 2 element but magnesium in an organic recipe, ever. MAYBE calcium as a counterion, because calcium salts are more often insoluble while calcium ion itself is completely inert. Sr and Ba are like calcium but way more expensive and equally useless. Be is... actually just alien tech, I'm pretty sure, maybe we could use it but we don't bc its so rare and toxic. If anyone wants I'll post more about metals from an organic chemist's perspective.

Magnesium is EVERYWHERE bc it can form carbon bonds (grignard reagent RMgX is used to make dreaded carbon carbon bonds and is super easy to make, it's the first metal you learn) and the reduced metal doesn't immediately self destruct (like all other group 1 and 2 save Be) despite still being such a reducing agent it burns in pure nitrogen. Noble gases come in here, for being perfectly inert (save Xe) and Ar is the go-to inert atmosphere (similar weight and density to N2 or O2).

But, yeah, C H O N S P X M are the only REAL elements (in order), B and Si are Secret Elements, and everything else is a catalyst.

[labphoto]

Preparation of several Grignard reagents used for a specific reaction. 

Grignard reagents form via the reaction of an alkyl or aryl halide with magnesium metal. The reaction is conducted by adding the organic halide to a suspension of magnesium in an etherial solvent, which provides ligands required to stabilize the organomagnesium compound. On the above picture the Grignard reagents were prepared under nitrogen gas atmosphere and both the solvent and the halide was added to the magnesium with a syringe to prevent the contact with air and moisture.

Something interesting: François Auguste Victor Grignard (May 6, 1871 - December 13, 1935) discovered in 1900, that organic halides react with metallic magnesium forming a highly reactive compound what even reacts with carbon dioxide from air forming carboxylic acids. The reaction between the halide (RX) and magnesium (Mg) gives the Gringard reagent (RMgX) what is an organometallic compound, still widely used by chemists in a lot reactions. Victor Grignard was awarded the Nobel Prize in Chemistry in 1912 for his work.

[thechemistrynerd]

As promised my master post of all general organic chemistry reactions. Please credit me if needed and understand this took a very long time to complete. So respect my post and don’t be afraid to ask me any questions!

Disclaimer: Not every reaction contains practice problems or full details of the mechanism. The purpose of this master post is to help students start somewhere with synthesis reactions. Also, to have a list of the possible reactions that will be covered in organic chemistry. Some universities might cover more than what I’ve posted so message me if you need any other help or I should add anything to this master post!

First Semester of Organic Chemistry

Radical Halogenation - [x] [x] [x]

Initiation // Propagation // Termination

Substitution Nucleophilic Reactions - [x] [x] [x]* [x]

Walden Inversion // “umbrella flip” that occurs with SN2 reactions No stereospecificity in SN1 reactions Watch out for hydride shifts and degree of carbocations Solvolysis // solvent is the nucleophile Electrophile // Nucleophile // Leaving Group // Solvent

Elimination Reactions/Dehydrohalogenation - [x] [x] [x] [x]

Zaitsev’s Rule // non-bulky base favors more sub. alkene Hoffmann’s Rule // bulky base removes less-hindered protons Beta Hydrogens // anti to leaving group

*Contains information for radical halogenation, SN and E reactions

Alkene Reactions - [x]

Syn // same side Anti // opposite side Hydrogenation Palladium // catalyst of platinum on carbon  Markovnikov’s Rule // regiospecific to the more sub. carbon Acid-Catalyzed Hydration - [x] Hydrofluoric Acid // not a strong enough acid for this reaction Kinetic Product // Thermodynamic Product Oxymercuration Mercury // allows no rearrangement  Hydroboration Ozonolysis - [x] 

Alkene Practice Problems - [x] [x] Alkene Roadmap

Alkyne Reactions - [x]

Hydrogenation  Lindlar’s Catalyst // alkyne to alkene only! Hydration Alkylation of Acetylides - [x] Double Dehydrohalogenation

Alkyne Practice Problems - [x] [x] [x] Alkyne Roadmap

Alcohol Reactions - [x]

Primary // Seondary // Tertiary  Sodium Borohydride // doesn’t work with esters Lithium Alummunum Hydride // more reactive and does work with esters

Alcohol Practice Problems - [x] [x] [x]* *Also contains epoxide practice problems! Alcohol Roadmap

Epoxide Reactions - [x]

Pretty straightforward reactions Weak Nucleophile // more sub. side Strong Nucleophile // less hindered side

Epoxide Practice Problems - [x] Epoxide Roadmap

Second Semester of Organic Chemistry

Ether Reactions - [x]

Reaction with HX Breaks the bond at the oxygen connection to form two alkyl halides Williamson Ether Synthesis - [x] Alkoxy Mercuration Demeruration

Sulfide Reactions - [x]

Diels-Alder Reactions - [x] [x] [x]

Diene // nucleophilic with an electron donating group Dienophile // electrophilic with an electron withdrawing group Watch out for regiochemistry and endo product is preferred

Electrophilic Aromatic Substitution - [x] [x] [x]

Halogenation Halogens are deactivators but ortho/para directors Alkylation Rearrangement // a 2+ carbon chain can undergo rearrangement for a more stable carbocation Limitation // installing one alkyl group is difficult due to a reactive ring Acylation Clemmensen Reduction // removes the carbonyl and is preferred to overcome rearrangement Limitations // 1) unable to install more than one acyl group because the ring becomes less reactive 2) no reaction if the ring has a nitro group present Sulfonation Can be used to make ortho position more active Nitration Reduction Reaction // converts the nitro group into an amine Carboxylic Group Addition Gatterman-Koch Reaction The addition of an aldehyde, not a ketone!

Nucleophilic Aromatic Substitution - [x] [x]

Criteria // 1) must have strong electron withdrawing group 2) must contain an LG 3) the LG must be ortho or para to the electron withdrawing group Addition-Elimination Meisenheimer Complex // the intermediate where the negative charge is being shifted around the ring for stability Reservoir // negative charge is pushed onto an atom when the ring gets attacked by a nucleophile Halogens // F > Cl > Br > I, due to bond length and electron density Elimination-Addition - [x] Benzyne // funky intermediate where a triple bond is located on the ring

**Please note that I won’t go into detail about activators versus deactivators.

Aldehyde and Ketone Reactions - [x] [x] [x]

Oxygen Nucleophiles Dean-Stark // removal of water to create the two ethers Diol // forms a cyclic acetal  Hydration // addition of two -OH groups Sulfur Nucleophiles Raney Ni // neutral conditions Thiols // react similar to diols  Clemmensen // acidic conditions Nitrogen Nucleophiles Preparation // jones reagent, PCC, ozonolysis Imine // primary amine that forms a double bond between N - C Enamine // secondary amine  Oxime // the nitrogen is bonded to an -OH group Hydrazone // the nitrogen is bonded to another amine group Wolff-Kishner Reduction // basic conditions Carbon Nucleophiles Grignard Reagent - [x] // Wittig Reagent - [x] Addition of CN Oxidation of Aldehydes Tollen’s Test // works in the presence of aldehydes  Acid Chlorides 

Amine Reactions - [x] [x]

Synthesis of Amines - [x] [x] SN2 Reaction // alkylation of ammonia and doesn’t stop at mono- Reductive Amination // formation of an amine from a carbonyl  Gabriel Synthesis Note // only works with primary amines Acylation of Amines Acids Hoffmann Rearrangement Nitrene // Isocyanate Hoffmann Elimination Also, forms a terminal alkene in the process Nitrosation - [x] In Situ // formation that immediately react with the amine before anything happens Sandmayer Reaction Aromatic Diazonium Salts // CuCl, CuBr, CuCN...

Carboxylic Acid and Derivative Reactions - [x] [x] [x] [x]

Golden Rule // never expel H or C Proton Transfer // may or may not occue Fisher-Sterification - [x] Amides from Carboxylic Acids Acid Halides Water // Alcohol // Amine // LAH // RMgX // R2CuLi Acid Chlorides Water // forms a carboxylic acid Alcohol // forms an ester Formation of Anhydrides - [x] Ester Synthesis Hydrolysis // acidic conditions in water Saponification // basic conditions in water Alcoholysis // formation of a new ester from another ester Reaction with RM // adds R group twice Reaction with Hydride // adds H twice Aminolysis Reaction of Amides Hydrolysis // Alcoholysis // Aminolysis Synthesis of Dicarboxylic Acids - [x] Polycarbonates - [x] Polyurethanes Ring Opening Polymerization - [x] Remember // Acid Halides > Anhydrides > Esters > Amides Can only travel from left to right in synthesis

Enol and Enolate Reactions  - [x] [x]

Aldol Condensation - [x] Ketones // yields are small Crossed Aldol - [x] Note // watch out what product needs to be formed, the compound being added dropwise is important Alpha Halogenation Haloform Reaction Iodoform Reaction Hell-Volhard-Zelinsky Reaction - [x] Claisen Condensation - [x] Acetoacetic Ester Synthesis - [x] Malonic Ester Synthesis - [x] Conjugate Addition Robinson Annulation Kinetic Enolates

An Amazing Secondary Aid Book(s)

Organic Chemistry As a Second Language First Semester // Second Semester

[umehanas]

アンペグガール / Ampeg Girl (English Lyrics)

“ ----Ampeg and bass, Sansamp, dismal girl.”

Song Title: アンペグガール / Ampeg Girl Music: テヅカ / Teduka Vocals: Kagamine Rin

NND Link: http://www.nicovideo.jp/watch/sm31745119 Original Lyrics (Official): http://piapro.jp/t/Rmgx

Comments: "Ampeg” and “Sansamp (Sans)” are brands that sell amp and other electronic guitar/bass equipment.

In the end, There's not much meaning to lyrics, is there? Yeah, it's better when there's just noise there

Fool me with the roar from an Ampeg Roar out, bass!

1, 2, 3, there! Downtown, I can't breathe well Staring at the ground, searching for oxygen, Let's go walking

Yeah, whether at the edge of the roof, or even the studio, it's all full of unhappiness Because each person's thoughts set the mood off-key

The routine of life continues on without fail With the exception of you, nothing was supposed to change, but Because I lost you, My voice is nowhere to be found Since everything's become awful, I won't sing Saying things like that, I'm a meaningless girl Every walk back-- (Still, I'm scared), --at the same intersection I miss my chance to die

In the end, There's not much meaning to lyrics, is there? No, that's not right at all It wasn't that way at all, but...

Oh yeah, It's your fault that I've started to like carbonated water The same old, familiar studio, at nighttime I still feel you here A lot of different things all connect, huh And also, end Like that memory, and this memory, too, And also, us being together

From now on, With this voice, I'll kill All the things about me and you, who changed into an entirely different person

Even if this feeling is drowned out by loud noise, Even though that can disappear too, Bass, answer me At least until the morning, when I have to sleep alone

I set my aim, And smash through the Sans onstage, And now I'll sing, so For right now, let's forget it all!

[onlinechem]

Soft and Hard Acids and Bases

Soft and Hard Acids and Bases

What is the HSAB concept of acids and bases?

HSAB concepts or hard-soft acid-base concepts identify the products of Lewis acid-base.

According to Lewis concepts, an acid-base reaction involves an interaction of a vacant orbital of an acid and a filled or unshared orbital on a base. In considering the acid-base equilibrium

Lewis acid + Lewis base ⇌ acid-base product

What are the hard bases?

The donor atoms of the first group have high electronegativity, Low polarisability and hard to oxidize. Such a donor has been named “Hard” bases by Pearson.

Examples of hard Bases: F-, OH-, NH3, N2H4, ROH, H2O, SO4-2, PO4-3, etc.

What are the soft bases?

The donor atoms of the second category have Low electronegativity, high polarisability and easy to oxidize. Such a donor has been named “Soft” bases by Pearson.

Examples of soft bases: H-, R-, CO, PR3, C6H6, SCN-

Hard and soft acids

Hard acids have small acceptor atoms, are of high positive charge and do not contain unshared pair of an electron in their valence shell.

Examples of hard acids: H+, Li+, K+, Ca2+, Al3+, Sn4+, BF3, BCl3, CO2, RCO+, SO3, RMgX, VO2+, AlCl3, etc.

Soft Acids have large acceptor atoms, are of low positive charge and contain unshared pair of an electron in their valence shell.

Examples of soft acids: Cs+, Cu+, Au+, Pt2+, Hg+, BH3, Br2, I2, RO+, quinones, etc.

HSAB concept of acids and bases

Hard acids prefer to bind with hard bases and form a stronger chemical bonding with them. Soft acids prefer to bind with soft bases and form stronger bonds with them. ​

More topics for chemistry courses

Van't Hoff equation

Shielding electrons

Chemical kinetics

Ionization energy

[omokoshaban]

Reduction of Aldehydes and ketones

Reduction of Aldehydes and ketones

Addition of organometallic reagents to Aldelydes and ketones

Organometallic reagents (RLI or RMgX) react with aldehydes and ketones to give alcohols.

Use of RLi

      1 . RLi     |

        R—C —OH

    2. H2O     |

  This reaction can be used to prepare primary, secondary and tertiary alcohols.

For example:

H

    |     + H2O

    HCHO + RLi R—C — O¯Li+     R—CH2OH

|

H

        …

[mountainghost-blog]

Organomagnesiums Market Profound Impact on the Market over 2021

Organomagnesiums belong to class of organometallic compounds which contain carbon-magnesium and other halide bonds.  Organomagnesiums are one of the major reagents used in organic synthesis, mostly used to transfer organic group through nucleophilic addition. Organomagnesium compounds should be handled only under inert gas environment for safety purposes. Inert gases like nitrogen or argon are usually used for this purpose. Addition of acids, water or any oxiding materials to organomagnesium compounds mainly due their high reactivity. Organomagnesiums find large number of industrial applications primarily due to their nature to bind with halogens and other halides through single electron transfer process. Organomagnesiums are commonly found as Grignard reagents like ethylmagnesium bromide phenylmagnesium bromide and several others. Phenylmagnesium bromide is a strong nucleophile as well as a strong base. It reacts with carbon di-oxide to give benzoic acid which has numerous applications such as precursor for plasticizers and sodium benzoate (for preservatives).The market for organomagnesium is largely dominated by the U.S, followed by Europe and then Asia-Pacific region. The organomagnesium market is largely affected by increased prices of raw materials and cheaper substitutes. The application in form of catalysts acts as a prime driver for organomagnesium market.

Request For Report Sample@ https://www.persistencemarketresearch.com/samples/4251

The use of organomagnesium as an effective reagent was first pioneered by François Auguste Victor Grignard and hence these compounds find their utmost application as a Grignard Reagent. The Grignard reagent is basically an organomagnesium halide (RMgX) having a positively polarized metal, which makes the alkyl group act as a carbanion. Organomagnesiums are used as agents to prepare alcohols, ketones, keto-esters, terpene and nitriles compounds. Organomagnesiums are also used to induce a substitution at carbon, which helps in carbenoid and arynoid reactions. Organomagnesiums can also be utilized for the formation of carbon-nitrogen bonds, carbon-sulfur, carbon-oxygen bonds, carbon-selenium, carbon-halogen bonds, and other organometallic compounds. Organomagnesium compounds reactions with pyridinium salts are more useful than those of organolithium compounds and hence can act substitution to organolithiums. Organomagnesium compounds play an imperative role as catalysts and are widely used for this purpose. Organomagnesium are used in synthesis of polyolefins. Polyolefins find range of industrial applications in production of thermoplastic polyolefin and polyolefin elastomers. Thermoplastic polyolefin such as polyethylene find a range of applications in packaging (plastic bags or plastic films), while polypropylene is used in packaging, labeling, stationery, plastic parts and reusable containers. Polyolefin elastomers such as polyisobutylene, ethylene propylene rubber can also be produced through organomagnesiums. Organomagnesiums to a certain extent are also used in synthesis of pharmaceutical and fine chemicals.

Request For Report Table of Content (TOC)@ https://www.persistencemarketresearch.com/toc/4251

Organomagnesium belong to the family of organometalics which are used across the globe for varied applications including those of stabilizers, catalysts for chemical reactions and for synthesis of pharmaceuticals. The market for organomagnesium as Grignard reagents is largely dominated by the U.S. and European region. However the increased environmental regulations can lead to shift of production of these to developing countries in Asia. Also the availability of better substitutes makes the market for organomagnesiums vunerable to these substitutes. The market for organomagnesium is expected to be steady across Europe and African countries. Organomagnesium market is expected to grow at a rapid pace across Middle East owing to increase in number of production facilities. Asia Pacific and especially China is also expected to be the upcoming market for organomagnesium in the next six years.

The major players operating in the global organomagnesium market are Rockwood Lithium GmbH and Rieke Corporation among others.

Know More About Report@ https://www.persistencemarketresearch.com/market-research/organomagnesiums-market.asp

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[9950964230]

12th class notes in hindi

MENU  अल्कोहल और फिनोल बनाने की विधियां Methods of making alcohol and phenols अल्कोहल बनाने की विधियाँ (Alcohol forming methods):

1.ग्रिन्यार अभिकर्मक से :

इस विधि द्वारा 10 , 20 , 30 एल्कोहल बनाये जाते है।

जब RMgX की क्रिया HCHO से की जाती है तो बने पदार्थ के जल अपघट्न से 10 एल्कोहल बनते है। जब RMgX की क्रिया R-CHO से की जाती है बने पदार्थ के जल अपघट्न से द्वितीयक…

[russurban]

Customized research for $RMGX vs. $LVHD!

http://speculatingstocks.com/stockcomparison/versus.php?stock1=15409&stock2=21125

[healthy-insights]

Organomagnesiums Market Intelligence with Competitive Landscape 2021

Organomagnesiums belong to class of organometallic compounds which contain carbon-magnesium and other halide bonds.  Organomagnesiums are one of the major reagents used in organic synthesis, mostly used to transfer organic group through nucleophilic addition. Organomagnesium compounds should be handled only under inert gas environment for safety purposes. Inert gases like nitrogen or argon are usually used for this purpose. Addition of acids, water or any oxiding materials to organomagnesium compounds mainly due their high reactivity. Organomagnesiums find large number of industrial applications primarily due to their nature to bind with halogens and other halides through single electron transfer process. Organomagnesiums are commonly found as Grignard reagents like ethylmagnesium bromide phenylmagnesium bromide and several others. Phenylmagnesium bromide is a strong nucleophile as well as a strong base. It reacts with carbon di-oxide to give benzoic acid which has numerous applications such as precursor for plasticizers and sodium benzoate (for preservatives).The market for organomagnesium is largely dominated by the U.S, followed by Europe and then Asia-Pacific region. The organomagnesium market is largely affected by increased prices of raw materials and cheaper substitutes. The application in form of catalysts acts as a prime driver for organomagnesium market.

Request Sample Copy of the Report @ https://www.persistencemarketresearch.com/samples/4251

The use of organomagnesium as an effective reagent was first pioneered by François Auguste Victor Grignard and hence these compounds find their utmost application as a Grignard Reagent. The Grignard reagent is basically an organomagnesium halide (RMgX) having a positively polarized metal, which makes the alkyl group act as a carbanion. Organomagnesiums are used as agents to prepare alcohols, ketones, keto-esters, terpene and nitriles compounds. Organomagnesiums are also used to induce a substitution at carbon, which helps in carbenoid and arynoid reactions. Organomagnesiums can also be utilized for the formation of carbon-nitrogen bonds, carbon-sulfur, carbon-oxygen bonds, carbon-selenium, carbon-halogen bonds, and other organometallic compounds. Organomagnesium compounds reactions with pyridinium salts are more useful than those of organolithium compounds and hence can act substitution to organolithiums. Organomagnesium compounds play an imperative role as catalysts and are widely used for this purpose. Organomagnesium are used in synthesis of polyolefins. Polyolefins find range of industrial applications in production of thermoplastic polyolefin and polyolefin elastomers. Thermoplastic polyolefin such as polyethylene find a range of applications in packaging (plastic bags or plastic films), while polypropylene is used in packaging, labeling, stationery, plastic parts and reusable containers. Polyolefin elastomers such as polyisobutylene, ethylene propylene rubber can also be produced through organomagnesiums. Organomagnesiums to a certain extent are also used in synthesis of pharmaceutical and fine chemicals.

Organomagnesium belong to the family of organometalics which are used across the globe for varied applications including those of stabilizers, catalysts for chemical reactions and for synthesis of pharmaceuticals. The market for organomagnesium as Grignard reagents is largely dominated by the U.S. and European region. However the increased environmental regulations can lead to shift of production of these to developing countries in Asia. Also the availability of better substitutes makes the market for organomagnesiums vunerable to these substitutes. The market for organomagnesium is expected to be steady across Europe and African countries. Organomagnesium market is expected to grow at a rapid pace across Middle East owing to increase in number of production facilities. Asia Pacific and especially China is also expected to be the upcoming market for organomagnesium in the next six years.

The major players operating in the global organomagnesium market are Rockwood Lithium GmbH and Rieke Corporation among others.

Request TOC of the Report @ https://www.persistencemarketresearch.com/toc/4251

[goodvibesandchemnotes]

My two favorite orgo reactions!

FISCHER RXN

The Fischer esterification is a reaction as essential to the beginner organic chemistry student as it is to the layman observing his fruit ripen. Esters are a weakly polar, organic compound of chemical characterized by the dehydration of an acid (generally carboxylic) and an alcohol; as such, they are named X-yl Y-oate for the alcohol X-ol and the acid Y-oic acid. As characterized by the carbonyl and the carbon-oxygen sigma bond, the compound is in between the polarity of a comparably sized ketone above (such as ethyl acetate and acetone) and ether below (such as ethyl acetate and diethyl ether), making them miscible with each but sparingly soluble in a highly polar compound such as water or glycerol [# pubchem etoac].

Esters are highly significant in the natural world and are even known among chemistry laymen, such as wine enthusiasts, for their generally pleasant odor reminiscent of fruit (aliphatic esters) or mint (aromatic esters). This stands in stark contrast to the acrid smell and taste of most carboxylic acids and alcohols. For example, butyric acid, a carboxylic acid, is named for being the primary component of rancid butter. This response is for a good reason, when bacteria grow in over-ripe fruit, they hydrolyze the esters into their constituents (enzymatically or with increasing acidity). Over many generations, animals evolved to detect the constituents with an unpleasant smell and/or taste and associate them with rotten fruit and therefore illness.

With a clever knowledge of chemistry, this natural process of hydrolysis can be directly reversed. An extreme pH is generally required to catalyze the hydrolysis of an ester, and the reaction equilibrium in nature is driven by an excess of water. Therefore, by le Chatelier’s principle an absence of water and an excess of alcohol or acid should drive the equilibrium in the opposite direction. Indeed this is the case: Fischer and Speier noted in 1895 that in dehydrating conditions (especially over 100 C) methanol or ethanol condensed with organic acids in the presence of mineral acids [#german source]. The ester can then be readily extracted from the reaction bath of alcohol and water with a weakly polar organic solvent like diethyl ether.

In this particular experiment, benzoic acid will be esterified with excess methanol under sulfuric acid catalysis to form methyl benzoate, a compound similar to the natural product wintergreen (methyl salicylate, or methyl (o-OH)benzoate. One should note that as well as aliphatic polar solvents (most commonly ethyl acetate is used as a non-toxic alternative to diethyl ether or acetone), esters are useful as protected precursors to other compounds. For example, the Grignard reagent RMgX is an extremely strong base and would deprotonate a carboxylic acid R'COOH rather than react with the carbonyl to form a carbon-carbon bond (as Grignard reagents are intended for); however, the ester R’COOR” reacts in the way one would otherwise expect of a carboxylic acid in forming carbon-carbon bonds with a Grignard reagent.

https://pubchem.ncbi.nlm.nih.gov/compound/ethyl-acetate#section=Solubility

https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cber.189502803176

GRIGNARD RXN

While the basics of organic chemistry had been known since the 1800s, and inorganic chemistry for much longer, the bridge between the two (rather directly named “organometallics”) was not understood until much more recently. The Grignard reaction is one of the first such organometallic reactions; Victor Grignard was the first to publish on the chemistry of alkylmagnesium halides RMgX (named Grignard reagents) in 1900 and was awarded a Nobel prize for this groundbreaking discovery in 1912. This discovery was so revolutionary that the field of organometallic chemistry was not even approached again until the 1930s, when organolithium reagents RLi were developed as a less sterically hindered alternative to Grignard reagents. The phenomenon of bridging two seemingly unrelated fields is significant on its own, but the discovery of Grignard reagents opened the door to modern chemistry by providing a simple and reliable way of forming carbon-carbon sigma bonds.

Carbon is a relatively neutral element with regard to electronegativity, and as such it does not readily react with other carbon atoms in molecules and preferentially reacts with more electronegative compounds. In the case of Grignard reagents, the imbalance is in the opposite direction, disrupting an already polarized carbon-halogen bond with the highly electropositive and reducing magnesium metal (via a radical intermediate). This C-Mg bond is extremely unstable (so much so that the Grignard reagent is almost exclusively generated in situ), with a strong ionic character almost resembling a persistent carbanion coordinated to an oxidized Mg2+ ion. A carbanion is extremely nucleophilic and will readily attack any electrophile (such as a carbonyl) by donating its lone pair to form a sigma bond. In the case of a carbonyl a prized carbon-carbon bond is formed, transferring the spectator MgX+ ion from the carbanion to the newly formed alkoxide ion. However, carbanions are also extremely strong bases (arguably stronger than they are nucleophiles), and any protic solvent such as water or an alcohol will act as an acid and donate a proton to form the corresponding alkane and a magnesium-solvent salt. Therefore, it is prerequisite in any Grignard reaction to keep the reaction completely dry of moisture and any protic solvent.

The Grignard reagent was first explored with carbonyl chemistry, and when named without clarification the “Grignard reaction” implies reaction of an alkyl- or aryl-magnesium halide (generally chloride or bromide) with a carbonyl of some sort. The traditional introductory example is the reaction of a Grignard reagent with a ketone to form a tertiary alcohol, where the addition is relatively straightforward and the resulting alkoxide is neutralized with acidic aqueous workup (generally with a HCl, leaving a byproduct of MgCl2 or the mixed MgClBr). The reaction with aldehydes follows similarly, forming a secondary alcohol instead, and the Grignard reagent will react with electrophiles including nitriles, alkenes, and epoxides, and (more unusually) esters.

The reaction of Grignard reagents with esters behaves most regularly in at least a 2:1 excess to the ester, where the carboxylate group is turned into a tertiary alcohol. The first equivalent of carbanion attacks the ester carbonyl to form a hemiketal, which is unstable with respect to the alkoxide leaving group from the ester and forms a ketone between the (formerly) carboxyl and the carbanion. By preserving the carbonyl from the ester carboxyl group, the intermediate molecule is open to a second attack by the carbanion to form a tertiary alcohol as described previously. However, when only one equivalent of Grignard reagent is available, the reaction will not proceed uniformly and a mix of the ester, tertiary alcohol, and intermediate ketone will be present in the product. In this experiment, phenylmagnesium bromide (itself formed from phenyl bromide and magnesium metal in situ) is reacted with methyl benzoate to form triphenylmethanol, via the intermediate benzophenone.

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