Objectives
After completing this section, you should be able to
- discuss the wide occurrence of esters in nature, and their important commercial uses, giving one example of an ester linkage in nature, and one example of a commercially important ester.
- write an equation to describe the hydrolysis of an ester under acidic or basic conditions.
- identify the products formed from the hydrolysis of an given ester.
- identify the reagents that can be used to bring about ester hydrolysis.
- identify the structure of an unknown ester, given the products of its hydrolysis.
- write the mechanism of alkaline ester hydrolysis.
- write the mechanism of acidic ester hydrolysis.
- write an equation to describe the reduction of an ester with lithium aluminum hydride.
- identify the product formed from the reduction of a given ester (or lactone) with lithium aluminum hydride.
- identify the ester, the reagents, or both, that should be used to prepare a given primary alcohol.
- write a detailed mechanism for the reduction of an ester by lithium aluminum hydride.
- identify diisobutylaluminum hydride as a reagent for reducing an ester to an aldehyde, and write an equation for such a reaction.
- write an equation to describe the reaction of an ester with a Grignard reagent.
- identify the product formed from the reaction of a given ester with a given Grignard reagent.
- identify the ester, the Grignard reagent, or both, needed to prepare a given tertiary alcohol.
- write a detailed mechanism for the reaction of an ester with a Grignard reagent.
Key Terms
Make certain that you can define, and use in context, the key terms below.
Study Notes
Many esters have characteristic aromas and flavours. Some examples are listed below.
Basic structure:
![general structure of an ester](https://chem.libretexts.org/@api/deki/files/106368/21-6a.png?revision=1)
Table 21.1 Structures and characteristic odours of selected esters
IUPAC name |
R |
R′ |
Aroma |
octyl ethanoate |
CH3 |
CH3(CH2)6CH2 |
orange |
propyl ethanoate |
CH3 |
CH3CH2 CH2 |
pear |
2‑methylpropyl propanoate |
CH3CH2 |
(CH3)2CHCH2 |
rum |
methyl butanoate |
CH3CH2CH2 |
CH3 |
apple |
ethyl butanoate |
CH3CH2CH2 |
CH3CH2 |
pineapple |
A “lactone” is a cyclic ester and has the general structure
![general structure of a lactone](https://chem.libretexts.org/@api/deki/files/106369/21-6b.png?revision=1)
By recognizing that the steps in the acidic hydrolysis of an ester are exactly the same as those in a Fischer esterification (but in the reverse order!), you can again minimize the amount of memorization that you must undertake. The details of both mechanisms can be deduced from the knowledge that both reactions are acid‑catalyzed nucleophilic acyl substitutions.
Esters are present in a many biologically important molecules, which have a wide range of effects including fats, waxes, Vitamin C, Cocaine, Novacaine, oil of wintergreen, and aspirin.
![clipboard_e4a4c475220b9572b674bebd137f0b7d2.png](https://chem.libretexts.org/@api/deki/files/351738/clipboard_e4a4c475220b9572b674bebd137f0b7d2.png?revision=1)
Esters compounds are often the source of the pleasant aromas of many fruits.
![21.6 fruit esters.svg](https://chem.libretexts.org/@api/deki/files/390378/21.6_fruit_esters.svg?revision=1&size=bestfit&width=645&height=98)
Esters are also present in a number of important commercial and synthetic application. For example, polyester molecules make excellent fibers and are used in many fabrics. A knitted polyester tube, which is biologically inert, can be used in surgery to repair or replace diseased sections of blood vessels. The most important polyester, polyethylene terephthalate (PET), is made from terephthalic acid and ethylene glycol monomers. PET is used to make bottles for water and other beverages. It is also formed into films called Mylar which is used in balloons. Synthetic arteries can be made from PET, polytetrafluoroethylene (PTFE), and other polymers.
![clipboard_e6bb5bdf561ebf0432b2085debb6ffb08.png](https://chem.libretexts.org/@api/deki/files/351740/clipboard_e6bb5bdf561ebf0432b2085debb6ffb08.png?revision=1&size=bestfit&width=505&height=247)
Lactones, cyclic esters, have similar reactivity as acyclic esters.
![](data:image/png;base64,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)
Preparation of Esters
The most versatile method for the preparations of esters is the nucleophilic acyl substitution of of an acid chloride with an alcohol. Acid ahydrides and carboxylic acids can also react with alcohols to form esters but both reactions are limited to formation of simple esters. Esters can also be formed by deprotonating a carboxylic acid to form a carboxylate and then reacting it with a primary alkyl halide using an SN2 reaction.
![](data:image/png;base64,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)
Reactions of Esters
Esters are one of the more useful functional groups. Their low reactivity makes the easy to work with and they are stable enough to be used as a solvent in organic reactions (ex. ethyl acetate). Esters are still reactive enough to undergo hydrolysis to form carboxylic acids, alcoholysis, to form different esters, and aminolysis to form amides. Also, they can react with Grignard reagents to form 3o alcohols and hydride reagents to form 1o alcohols or aldehydes.
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)
Conversion of Esters to Carboxylic Acids: Hydrolysis
Esters can be cleaved back into a carboxylic acid and an alcohol through reaction with water and a catalytic amount of strong acid. This reaction represents the reverse of the acid catalyzed esterification of a carboxylic acid and an alcohol discussed in Section 21.3. Both the ester formation and cleavage reactions are part of an equilibrium which can be manipulated using Le Chatelier's principle. For ester hydrolysis, the equilibrium is shifted toward carboxylic acid formation by using a large excess of water in the reaction.
General Reaction
![](data:image/png;base64,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)
Example
![](data:image/png;base64,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)
Mechanism
Acid catalysis is required during ester hydrolysis due to water being a weak nucleophile. Protonation of the ester carbonyl increases the partial positive charge on the carbonyl carbon increasing its electrophilicity. After protonation, water adds to the carbonyl carbon causing the formation of a tetrahedral alkoxide intermediate. Then a proton transfers to the –OR group, increasing its ability to act as a leaving group. Reforming the carbonyl double bond causes the elimination of an alcohol (HOR) as a leaving group, creating a protonated carboxylic acid. In the last step of the mechanism, water acts as a base, removing a hydrogen, to form a carboxylic acid and regenerating the acid catalyst.
1) Protonation of the carbonyl
![](data:image/png;base64,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)
2) Nucleophilic attack by water
![](data:image/png;base64,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)
3) Proton transfer
![](data:image/png;base64,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)
4) Leaving group removal
![](data:image/png;base64,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)
5) Deprotonation
![](data:image/png;base64,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)
Hydrolysis of Lactones
Lactones (Cyclic esters) undergo typical reactions of esters including hydrolysis. Hydrolysis of the lactone under acidic conditions creates a hydroxyacid.
![](data:image/png;base64,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)
Conversion of Esters to Carboxylic Acids: Saponification
Esters can also be cleaved into a carboxylate and an alcohol through reaction with water and a base. The reaction is commonly called a saponification from the Latin sapo which means soap. This name comes from the fact that soap used to me made by the ester hydrolysis of fats.
Saponification reaction utilize a better nucleophile (hydroxide) and are typically faster than an acid catalyzed hydrolysis. The carboxylation ions produced by saponification are negatively charged and very unreactive toward further nucleophilic substitution which makes the reaction irreversible.
General Reaction
![](data:image/png;base64,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)
Example
![](data:image/png;base64,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)
Mechanism
The base-promoted hydrolysis of an ester follows the typical nucleophilic acyl substitution mechanism. A full equivalent of hydroxide anion is used, so the reaction is called base-promoted and not base catalyzed. The mechanism of ester saponification begins with the nucleophilic addition of a hydroxide ion at the carbonyl carbon to give a tetrahedral alkoxide intermediate. The carbonyl bond is reformed along with the elimination of an alkoxide (-OR) leaving group yielding a carboxylic acid. The alkoxide base deprotonates the carboxylic acid to for a carboxylate salt and an alcohol as products.
The last deprotonation step essentially removes the carboxylic acid from the equilibrium which drives the saponification towards completion. Because the carboxylic acid is no longer part of the equilibrium the reaction is effectively irreversible.
1) Nucleophilic attack by hydroxide
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)
2) Leaving group removal
![](data:image/png;base64,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)
3) Deprotonation
![](data:image/png;base64,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)
This mechanism is supported by experiments performed using isotopically labeled esters. When the ether-type oxygen of the ester was labeled with 18O, the labeled oxygen showed up in the alcohol product after hydrolysis.
![](data:image/png;base64,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)
An alternative mechanism would be if the hydroxide participated in an SN2 reaction to create the carboxylate product. If this were to happen the alcohol reaction product would not contain the labeled oxygen.
![](data:image/png;base64,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)
Ester saponification in biological systems, called hydrolytic acyl substitution reactions, are common. In particular, acetylcholinesterase, an enzyme present in the synapse, catalyzes hydrolysis of the ester group in acetylcholine which is a neurotransmitter that triggers muscle contraction. Like many other hydrolytic enzymes, the acetylcholinesterase reaction proceeds in two phases: first, a covalent enzyme-substrate intermediate is formed when the acyl group of acetylcholine is transferred to an active-site serine on the enzyme (a transesterification reaction). A water nucleophile then attacks this ester, driving off acetate and completing the hydrolysis
![clipboard_ed00a16db58fdc725c04841117f1c85ef.png](https://chem.libretexts.org/@api/deki/files/351741/clipboard_ed00a16db58fdc725c04841117f1c85ef.png?revision=1)
Conversion of Esters to Different Esters: Transesterification
Transesterification is a reaction where an ester is converted to a different ester through reaction with an alcohol. Because there is typically very little difference in stability between both esters, the equilibrium constant of this reaction is usually near one. Using a large excess of the reactant alcohol or removing the alcohol side-product can push the reaction equilibrium towards the products by Le Chatelier’s principal. Transesterifications also shows that great care should be taken when an ester containing compound is used in a reaction involving an alcohol.
General Reaction
![](data:image/png;base64,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)
Example
![](data:image/png;base64,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)
Mechanism in Basic Conditions
The reaction follows the basic mechanism of a nucleophilic acyl substitution. The alkoxide leaving group of the ester is replace by an incoming alkoxide nucleophile creating a different ester.
1) Nucleophilic attack by an alkoxide
![](data:image/png;base64,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)
2) Leaving group removal
![](data:image/png;base64,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)
Mechanism in Acidic Conditions
Protonation allows the alcohol reactant to add to the ester carbonyl. Proton transfer to the ester's alkoxy group increases it ability to act as a leaving group. Reforming the C=O carbonyl bond removes the leaving group and subsequent deprotonation by water forms the ester product.
1) Protonation of the carbonyl
![](data:image/png;base64,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)
2) Nucleophilic attack on the carbonyl
![](data:image/png;base64,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)
3) Proton transfer
![](data:image/png;base64,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)
4) Removal of the leaving group
![](data:image/png;base64,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)
5) Deprotonation
![](data:image/png;base64,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)
Conversion of Ester to Amides: Aminolysis
It is possible to convert esters to amides through direct reaction with ammonia or amines. However, these reactions are not commonly used because the formation of an amide using an acid chloride is a much simpler reaction.
![](data:image/png;base64,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)
Conversion of Esters to 1o Alcohols: Hydride Reduction
Esters can undergo hydride reduction with LiAlH4 to form two alcohols. The alcohol derived from the acyl group of the ester will be 1o and is typically considered the main product of the reaction. The other alcohol is derived from the ester’s alkoxy group and is typically considered a side-product of the reaction. Note! Sodium borohydride (NaBH4) is not a reactive enough hydride agent to reduce esters or carboxylic acids. In fact, NaBH4 can selectively reduce aldehydes and ketones in the presence of ester functional groups.
General Reaction
![](data:image/png;base64,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)
Predicting the Products of a Hydride Reduction
There are three major changes in bonding during this reaction: 1) The –OR leaving group is removed from the ester. 2) The C=O carbonyl bond is converted to a C-O-H, an alcohol. 3) Two C-H bonds are formed as two of the hydride nucleophiles are added to the original carbonyl carbon of the ester.
![](data:image/png;base64,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)
Example
![](data:image/png;base64,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)
Mechanism
The mechanisms for the hydride reduction of esters is analogous to the hydride reduction of carboxylic acids. Nucleophilic acyl substitution replaces the –OR leaving group in ester with a hydride nucleophile to form an aldehyde intermediate. Because aldehydes are more reactive than esters, they rapidly undergo a second nucleophilic hydride addition to form a tetrahedral alkoxide intermediate. An acid work-up protonates the alkoxide to create a 1o alcohol.
1) Nucleophilic attack by the hydride
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)
2) Leaving Group Removal
![](data:image/png;base64,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)
3) Nucleopilic attack by the hydride anion
![](data:image/png;base64,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)
4) The alkoxide is protonated
![](data:image/png;base64,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)
Conversion of Esters to Aldehydes: Hydride Reduction
Much like acid chlorides, esters can be converted to aldehydes using the weaker reducing reagent diisobutylaluminum hydride (DIBALH). As shown above, an aldehyde intermediate is produced after an ester undergoes nucleophilic acyl substitution with a hydride. When DIBALH is used as the hydride source, the aldehyde does not react further and is isolated as the product of the reaction. The reaction is usually carried out at -78 oC to help isolate the aldehyde product.
General Reaction
![](data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAg0AAAB/CAYAAABsbfF3AAAOj0lEQVR4nO3dz2sUaR7H8bo16ZsHBRlv9j8wB+8JjKDeZGCyQm4zzN5nlYEcBJ2FYYkHCYMwLLrKguOPvehAZGRZNkzvamJgyKKgsKA4gggjaU9dt+8e3Kfz9JOnqr7VVlU/T/X7BX1JOpWnu5/nW5+qeurpRAAAABSSaTcAAADEgdAAAABUgg4NaTqUO7euyvzCR5IkiSRJIocW5uVef1OGaTrt5gHAxKhviFGwoSFNh/LVp5+MBpP7OHryNAMLpV08e0qSJJFL1++PfvbyxVM5PDc39jPXYPCbHN9/wNsXDy3My7Wbd8f6o9lmt9OTZ89/zf17s42HW9ve/222lSSJHNx3Qt4OBpltW998sufvHz9az/xbTAf1DbEKNjT8dOM7SZJEup2e3Otvjn6+0V8bFdC8Ig+4Nvpro6Js9x1TwPN2qkU7fbfQlw0N5uHb6ZuxkPUcQkN8qG+IVZChgSKIKqXpUC6vnBvb8boF2XcGwpbXJ32FPi80uH9vH3UuLa96f9ft9OTM1194n8N4iQufF2IWZGgoGjRm0JmCDGSxd8iHFuZH14/dcGD6XNZp4aJCb44cTZ8tExrsv3f/v9nO0ZOn5emzX+Tw3NyeccFOKC7UN8Qs6NCQVcDtHYGvSAJGmg7lm88/l2s378rOu51Rv3FDg9k5FxXyrD7nhoQyoeHN61eZ7TJhYml5NbPfExriQn1DzAgNmBl2v3F3zkVHd0U7ZvfvJ5nT4PZ3Xz+3Q4SvbXkPQkMYqG+IWdChgdN3qJImNBSFgjpDQ7fTG9u27+yH72eEhrhQ3xCzIEODXQR9E9Pc68eARl5oKDq6q/PyRJoO5YerK3v6tHvXRNadFlyeiAv1DTELMjSI7M5m55YkVKXOMw3ujrnsREj36LLoPn77EgWhIT7UN8Qq2NDA4ieoWl1zGra3HnzQLZciIj//eHu0E/GdqbC5IYDQEB/qG2IVbGgQyV5m1V19D9DICw1l7p7QFPpJF3cyZw+ybsF027K++YTQECnqG2IUdGgAqpQXGsqs0+A+qlhGutvpyYUrN2SYprntNMzp7aXlVUIDgMYQGgDZPbLnOjIAZCM0YOZpvnsCABBJaEiSvc30/QyYhLmU4H6nA9AE6htiEkXPZFABaCvqG2ISRc9kUAFoK+obYhJFz2RQAWgr6htiEkXPZFABaCvqG2ISRc9kUAFoK+obYhJFz2RQAWgr6htiEkXPZFABaCvqG2ISRc9kUAFoK+obYhJFz2RQAWgr6htiEkXPZFABaCvqG2ISRc9kUAFoK+obYhJFz2RQAWgr6htiEkXPZFABaCvqG2ISRc9kUAFoK+obYhJFz2RQAWgr6pvfTze+kyRJ5OjJ0zJM08b+72Dwmxzff0CSJJH1zSd7fv/40bokSSIH952Qt4PB6OdpOpQ7t67K/MJHkiSJJEkihxbm5V5/s9H22+zX4nuY9hkvXzyVw3Nz0u305NnzX73bjKJnMqgAtBX1zS+m0JCmQ/nq008yd85NvwajKDSYh3mdhAYAU8U4LUZ984spNJi2dju9sSP3jf6aHJ6bkyRJ5NL1+429BiPvtdhBx7zH5vnuWRRbFD2TQQXEyT2iwV7Ut11mhzzNI/ayoWHSyxlN0LbNvK8mSOS9z1H0TAZVPIpOg/HgYT9AfbPFGBqKQoHZXt4p/7pozzQsLa+qtxlFz2RQAfEiMOSjvvmFcHki7+GGhqx22jtnXwiZ9mspG2ai6JkMKiBOhIRi1De/toeGJs7k5b2Wbqcn127eLf3eRtEzGVQA2or65hdCaGjj5YmN/tooOJz/0xVCAwDEhPoWlg+ZCOm7Q8KEn5AmQpo2ZbU5Dz0TAID/m+RuiItnT41O+cdwy6V9yaSVcxq2tx7Il4uLY9dizpy/IK9ev5l20xpVZnUvzSIdAKaP+haWti7u5L4Ws48o277gQ8PllXOVzfqMXZnVvQgNQPiob+GpehnpSSYbVkX7WsqcCQk6NJgX5J7y2d56MFFCil2Z1b1ev3lVuLIXgOmhviFGwYYGeyeYNblk1k7hlVnda+fdTuHKXgCmg/qGWAUbGji9vlcdq3sBaB71DbEKPjRwen1XHat7AWge9Q2xIjREpI7VvQA0j/qGWAUfGjhy3lXH6l4Amkd9Q6yCDQ1FE4UeP1qX3332e/nvi+fNN25K6ljdC0DzqG+IVZChwSyhanaG3JL0Xh2rewFoFvUNMQsqNJijZVuZxU98fx87+/XUsboXgGZQ39AGQfTAosGwvfVAPjvxsXqZ1bYMLvc11LG6F4D6Ud/QFlPveXV2/lgHFkUBaIc6xzI1AtMwtV7X1I4xph1wTG0FkI36hrZqvLdNq5OHPLhCbhvCZy5LcUlq+qhvaLtGe1kInTq0wRVSW2bRzz/eHk0gdde6MJNLi3bGk34rXpasb8u719/0TnAlNIQhhLEcWn1D+zTSu0LsyNNuT4jvyay5ePaUd9a6+e4Ocytr0c6+ytBg3z7re9h3xtjrc/jaj2aEOJZDaw/ao9aeFeJgsk2jfaG/J7PC3tGbI3SzuqZ9q5sJFnlH8VWGhqx79zf6a6MzIm5bONMwHaGP5dDbhzjV0qNi66xNtDe296TtXr54KvMLH43tyH07f/vrxrPWvqgqNEy6HUJDs2Iby7G1F2GrvCfF3DnrGlwxvyezxPd9AJovFqoqNBQ9z/wfVv2cnpjHMuEBVRjrQUVfvWwmY3k31KIO6XsdZSenme205T1pO3sugT0nQLOj1nxleZnQkHVWw26jL5wgH/XtPfd1VD2RF+1WKjSYh92x2jSYbPbrKjM5zf1bhM/+fN3CWFRQ3ecQGsJFfdtlvyZCA8rIDA1u57EL1qx9t8Ekk9MQh6Iv+9LsqMsWXbvfHDm2OPqfXJ6oF/XNj9CAMtShQUQ3KaxtGFDt5Z5h8K31X/ZMQ1EfefzssRzff0CWllf33NLpu6PDZsIrfW0y1Dc/ahzKmOhMwyzdB87RX3uZ2yk18xW0cxrKFF0zpuydlN0mzmpVi/rmR2hAGaXnNMzazpHrzO1kf5V43nXtuu6eyAojZefPQI/65lfVnBzMBnVo6HZ6cu3m3ZkrWISGdspaTdENDXWv03Dx7CnvGQjfnTqzOP6qRH3zIzSgjMLLE2aVvCQZX5d/VnB5YraZcFHXJQHTvwic9aO++XF5AmWo5jTYR2Wzdj2VyWmzS/vdEx+C0NAc6psfoQFlqEJD0W1pbcfktNlk5jNUOTHOXvI5TYfeyxOoB/XNj9CAMtR3T9gTx2ZtMhaT01Al++u4jxxb9N7qiepR3/wIDShjonUaZvHImslpQNyob36EBpTRvvVRAQBALQgNAABAhdAAAABUCA0AAECF0AAAAFQIDQAAQIXQAAAAVAgNAABAhdAAAABUCA0AAECF0AAAAFQIDQAAQIXQAAAAVAgNAABAhdAAAABUCA0AAECF0AAAAFQIDQAAQIXQAAAAVAgNAABAhdAAAABUCA0AAECF0AAAAFQIDQAAQIXQAAAAVAgNAABAhdAAAABUCA0AAECF0AAAAFQIDQAAQIXQAAAAVAgNAABAJZrQMBj8Jsf3H5AkSTIfB/edkLeDgXqb73Z25PLKOVnffFJjywHE4OWLp3J4bi6zlpjfa+rM40frpWqSXd/qqkdl24S9ivqI/Zw63ucq+8mk7ZzZ0JCmQ/nq009qHaQA4vHTje/G6olbFwgNKOojIoSGYFQ9qAgNAAxTD7qdnpz5+gtJkkSWllfHnkNomG2aPiJCaAhG2TfrzetX8uXi4igRdjs9udffFJHxwOA7S/Hzj7dHp6C6nZ787U5/Tzu6nZ5c+cul0Zv+6vWbel44gNqZAnr05Gl5+uwXbzHNK7J2zThybFHu3Lo6UV1JkkTu9Tfl8sq5UW06c/6CDNM0twZePHtKkiSRS9fvl2pTUbuwS9NH7Oe5v9vor43eZ/tzdf/2sxMfj55z5NiiPNzaHv1e00+02yM0ZDzXfaxvPskNDWbwuQ8zGH3bPnry9J4PC0A8zGnnpeXVzLOQWUXWPWVdVV2xH+aI1m6nYR/IPHv+q7pNIlLYLuzS9BERfz/J+jzsfYc5E+R7mANebT/RbG+mQkPWw3R082b4BpH5kHwfuv0mmjMH7htrt2NpeVWGaSo7O++m86YA+GC+WuDbOfuKrK8e2Ns7uO+EbP3nYam6cvTk6dHzfri6Mraj97XB7BxMbdO0yd1WVrvwnraPiOR/tln7qKzPzP38tf1Esz27X858aLCf2+305Mz5C/Jwa3vsbICvE+QlM/O8Jq49AmiOb0f5IT8TGZ8/8Pd/3J64rrjzEHx1y5wt8B38ZLXp7WCgqnd4r8xn7/5cE8SynuP2C20/0Wzv++t/nZ3QoOnM7rUcN1jkJUfN4LbPYgCIl2bci/gLe9bkQvu5f/7+j5WFBru9S8uro78r26a3g4H6dUPfR0T2vs+aCahZz7H3U5eu31f3E832znz7LaHB593Ojvzr3/8czXY1O/u80JA3R4HQALSHb36T+zCnn/OONt16YBdtExo0dUUTGux2mLMYvssoeW2yQwNzsvKV6SMinGkIRpnQYL+BZtC4A8lNcPZzkmR34slGf23swyA0AO2RtYMV0RVi37XjN69feec0aOqKJjSIjE9gdNuuaZP9evLahXJ9xH6+77O9cOXG6PMwZ8LdMwjaOQ15/YQ5DaKb0+ALBO7DTtW+gaed5UxoAOKXd7TtFuim7p7QhAZ7PoKv7dw9UZ0yfUSk3N0TvstKeZc/yvSTou1x94STuNN0KCvf/GHs9+59rPa8BzOD2KQxzToNhAYgXr6zjS6zU11aXv2gdRq0dUUbGnwz8l2adRqK2jXryvYRkXLrNLjr+2xvPVCv06DpJ3nba31oAAC8l3fKHKgToQEAImHPQ7CPboGmEBoAIBJ2aDhybJHJimgcoQEAAKgQGgAAgAqhAQAAqBAaAACACqEBAACo/A8zHxEnPICKWwAAAABJRU5ErkJggg==)
Example
![](data:image/png;base64,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)
Conversion of Esters to 3o Alcohols: Grignard Reagents
Addition of Grignard reagents converts esters to two alcohols, one 3o alcohols (main product) and one 1o alcohol (considered a side product). The Grignard reagent adds to the ester twice, once during a nucleophilic acyl substitution to form a ketone intermediate then again during a nucleophilic addition to form the 3o alcohol product. Overall, during this reaction two C-C bonds are formed on the ester’s original carbonyl carbon.
General Reaction
![](data:image/png;base64,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)
Predicting the Products of a Grignard Reaction
![](data:image/png;base64,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)
Example
![](data:image/png;base64,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)
Mechanism
In the first two steps of the mechanism, the OR leaving group from the ester is replaced by the R group from the Grignard reagent through a nucleophilic acyl substitution. This forms a ketone intermediate which is not isolated because ketones, which are more reactive than esters, rapidly undergo nucleophilic addition with a second equivalent of the Grignard reagent to form an alkoxide intermediate. An acid work-up protonates the alkoxide to form the 3o alcohol product.
1) Nucleophilic Attack
![](data:image/png;base64,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)
2) Leaving group removal
![](data:image/png;base64,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)
3) Nucleophilic attack
![](data:image/png;base64,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)
4) Protonation
![](data:image/png;base64,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)
Example \(\PageIndex{1}\)
How could the following molecule be made using a Grignard reagent and an ester?
![](data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAIkAAABoCAYAAADFPNPuAAAJRElEQVR4nO2dra+bXhjHT5ax3O3i+QuQUxP8AcjOoZZgq6bwNcuCqlrqkDUbtpbkihrEEgyZwDSZ4AoUAoX5/sQv5wxuobyUt94+nwSxjq6sfHrOc16eBwaCaIDNfQHE8iFJiEZIEqIRkqSGLMtwOBxg2zYMw4BpmnBdF2manp3reR4cx7n4bzmOA9/3x7zk0SBJKgiCAIqigDEGVVVhGAZkWQZjDJIkIQiC0vmGYYCx+q8ySRIwxrDZbMa+9FEgSV7g+z4YY9A0DVEUlf4uDEOoqgpJkhCGoXidJLkj8jyHoiiQJKmyWwGA0+kESZIgy7I4hyS5IzzPA2PsYnwBAK7rgjEmYgyS5I7YbrdgjJW6kirSNAVjDNvtFsA/ScIwrDyOxyNJ8lowTROMsdqupghjDIZhAPgnSdNBkrwC+M3O87zxXB7cFt/nOE7lwVsokuQVYFkWGGM4nU4Xz4vjuLIlqYNiklcED1wPh0Or8/b7PQCS5K7gQ2BFUWq7nKphMklyZxwOBzDGsFqtEMdx6e/SNMVqtTobJpMkd8jhcIAkSUIWwzBKI5jdblc6nyS5U9I0heM4QhDDMGDb9lnrAtACH0GQJEQzJEkDvKvIsmzuS5kNkqQBHnQmSTL3pcwGSdIASUKSNEKSkCSNkCQkSSMkCUnSCElCkjRCkpAkjZAkJEkjJAlJ0ghJQpI0QpKQJI2QJCRJIyQJSdLIElaBwzCE67pwHAdhGJ7tv83zHGEYVm6I4iRJgjAMe/0/SJIFs9/vRXWD4qEoCo7HozivzfZIx3FaZSdWQZIsFNu2wRiDrutwXRdxHCOOY7iuC1VVwRgTopAkM5HnOY7HI9brtdjjul6ve33JXeG5w5qmVaZ2JEkCSZJE6gdJMgNZlkHXddG8G4ZR+vPYu9757vtLMcZ+vxexEkkyMUVBjsdj6ZecpqlIBXVdd5TPz/O8lGfcBpJkYjabzcUaJW2y/K6B5xmv1+vW7+GStDlIkgHQdR2qql48hweRfUjTVNQt8X1fVB7gQ9PT6dS5S+OSKIpSyhMqHjzYLUqSJAk8zzsr+/USkqRAlmWdf8X8fcW5DMdxYFnW2Q2qOmRZhmEYJekkScJqtWr9+X26m91uB1VVsd1uoarqxeSyySR5fn6GZVl4enqa6iM7E0VRqYJRW8IwPLvpfDTEpXFdV7QgTaUteLXHSwRBAMdxkCRJZ0nSNC3VfOOjpbqJttElyfMc+/0ej4+PeHh4AGMMlmW1qiY0Nfxm27Y963XsdrvSPEgV6/Va1FK5NnDlxQJnkcT3fVHS0nEc5Hle+dpS4F82L04zF2maQpIkSJJUGS8UKx8A/Uc3eZ5js9lAVVV4nlf73lEkOZ1OYqxf1Wrw1kWW5bMp5rlRVRWKolw8x7ZtaJo26sQaL5TDZeDdFv9eVVUtdRd9JMmyDJ7nYb1eY7Va1bbug0qSpqmYTl6tVo1Rc9fzp4DXN6uLS9I0HXUIXCQIAlHsjx+SJGG73Za6hiHmSXRdrw1eB5PEdd3eLUNTyzMWeZ7DcZzSrzLLMrGo5rpu6WbEcVyaaLtVgiCAZVml10zTrP1hXC1JEATQNG2QGGPKeOV4PEJRFMiyjP1+X/qs0+lUGrbqug5N08QvmddKu1X4hCCfNT4ej5BlubYl7y1JHMeiKVyv14P9+seOV6IoEiWtbNuuve48z+F5XukpFXzI+RoIwxCWZUGSJGiadvZQhSKdJcmyTPTbuq53Ct6iKLp4Y4oMHa8U110Mw2icqyD+0UmSYtzRVMayCv6IkKomvo5r4xUed0iSBFVVBylJlec5dF2/OGx8TbSSpBh37Ha7q7by9b1pfeKVS3HHtWw2m0lGOEvgoiQv444h++M+zX/beKVt3HENfGq76xT+LVIpyTVxR1f63NCiYMV4pe71sXBdF5Ik9V4RvhXOJPn+/Ts+fPgAWZZH21hTRZ+uoSjYp0+f8Pbt28lncHVdh2mak33eHJxJIssyvnz5MksKQd945devX3h8fMTXr18njxH4yvGt1mhtw5kkjLHZo/au8Qqflp5ik3IVlmVBVdVXG8QuUhJO23hlbkn4qm3TY9lulUVLwinGK1VB4tySAP+C2CXuk7mW1pLwpeu5yPO8dgJvCZLwCbauWx9vgZuR5BJLkAT4fz2kLqHqliFJiEZIkpGIokiM0IqJ3q7rlloa/r1eigObnqczNiTJCPCHSxe3Htq2LTYzmaYpRCFJJmJJkvAd96qqVk5I8rUwPptNkkzEkiTRdb12lzvwL8eFT+WTJBOxFEn65PGSJBOxFEl4XZGXD3K8BP9ei9l+Lw++33YuSJIB4UlTXXbtFfNrmo65IEkGJAiC3i1Jl+7meDyK1A7TNEdfsSdJBqRtVYIkScSN7SoJ3xEXRZFI0xx7KYAkGRhVVRu3DRTLXXWVJIqiUnfGFz/HhCQZGL7tsy7l0vf9UmvTd3STZRl834emaZ26tz6QJAOT57kYjWw2G3FNaZpiv9+Lqol8U3lfScIwhK7rkGX5YmLVEJAkI5CmqbixLw9d10s77a6dJ+EzvGNmFpIkIxLHMQ6Hg5jvqLo+XkPt0mal0+kk3ltVr03TtFE3ipEkN4bv+6WkMF6Ib8y0jtaSBEEwawWgOI5rE6HuSRLg/+5H0zTYtj3J3trF73F9mShW1SzfmyQARJG+KRLDFi1J2wT1e5RkSiolmTJzr4quCerPz89gjOH3798TXeF9cSbJmzdv8PHjx1nqd/RJUM+yDN++fcP79+9vukTVkjmT5OnpCZ8/f25MiBqSLMuw2+0gSVKnBPXD4SCK3P348WPkq7xfase0vB7IGLU9ihRvdNsldj7bOES9FKKZixMfxXogQ1UJ4vS50UmSiErIQ9dLIeppNTtWrF92bb2xPje6b3dEDEOnKdRrKwh5nndV3NGnThtxPb3m2fvWIuNrGW2guGM59F6MGaOqIVDujkzTfPWlpm6Bq1fshqqPWow7morPEtMy2LJuFEVic27XeIXHHVPXaSPaMfjaf/GGN8UrPO5gjJ09eYFYDqNsECl2HVXxCsUdt8Wou4iKMhiGgT9//lDccYNMstUsCAJ8+vQJ7969w8PDw6jT/MTwTLof8efPn/j79++UH0kMwDI3rRKLgiQhGiFJiEZIEqIRkoRohCQhGvkPc3BIpvfp99gAAAAASUVORK5CYII=)
Solution
The key bond breaks for this example are two C-C sigma bonds between the carbonyl carbon and two alpha carbons. Reactions with esters involve a double addition of the Grignard reagent so the fragments removed must be the same. In this example, the C-C bonds involving the two methyl groups are broken. Breaking these bonds separate the target molecule into the required starting materials. The fragment which contains the alcohol carbon forms a C=O carbonyl bond and gains an –OR to become an ester. The R group of the ester is largely unimportant to the overall reaction and is typically a methyl or ethyl group. The alkyl fragments gain MgBr to form a Grignard reagent. Remember that the Grignard reagent only contains one alkyl fragment.
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)
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)
Exercises \(\PageIndex{1}\)
1) Why is the alkaline hydrolysis of an ester not a reversible process? Why doesn't the reaction with a hydroxide ion and a carboxylic acid produce an ester?
2) Draw the product of the reaction between the following molecule and LiAlH4, and the product of the reaction between the following molecule and DIBAL.
![]()
3) How might you Prepare the following molecules from esters and Grignard reagents?
(a)![]()
(b)![]()
(c)![]()
- Answers
-
1) The reaction between a carboxylic acid and a hydroxide ion is an acid base reaction, which produces water and a carboxylate anion.
2)
![]()
3)
(a)![]()
(b) ![]()
(c)