5 Difference Between Acetal And Hemiacetal With Examples

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What Is Acetal?

Acetals are geminal-diether derivatives of aldehydes or ketones, formed by reaction with two equivalents (or an excess amount) of an alcohol and elimination of water. Ketone derivatives of this kind were once called ketals, but modern usage has dropped that term. It is important to note that a hemiacetal is formed as an intermediate during the formation of an acetal.

An acetal is a functional group with the connectivity R2C(OR’)2). Here, the R groups can be organic fragments (a carbon atom, with arbitrary other atoms attached to that) or hydrogen, while the R’ groups must be organic fragments not hydrogen. The two R’ groups can be equivalent to each other (a “symmetric acetal”) or not (a “mixed acetal”). Acetals are formed from and convertible to aldehydes or ketones and have the same oxidation state at the central carbon, but have substantially different chemical stability and reactivity as compared to the analogous carbonyl compounds. The central carbon atom has four bonds to it, and is therefore saturated and has tetrahedral geometry.

Acetals are used as protecting groups for carbonyl groups in organic synthesis because they are stable with respect to hydrolysis by bases and with respect to many oxidizing and reducing agents. They can either protect the carbonyl in a molecule (by temporarily reacting it with an alcohol) or a diol (by temporarily reacting it with a carbonyl). That is, either the carbonyl, or the alcohols, or both could be part of the molecule whose reactivity is to be controlled.

What You Need To Know About Acetal

  • Acetal is a group of atoms that is represented by a central carbon atom bonded to two-OR groups, -R group and a –H group.
  • The general formula of an acetal can be given as RHC(OR’)2.
  • Acetals are formed when aldehyde or ketone reacts with an alcohol in the presence of an acid catalyst. In this case the hydroxyl group of a hemiacetal becomes protonated and is lost as water. Loss of the proton from the attached alcohol gives the acetal.
  • Acetal is more stable when compared to a hemiacetals but their formation is a reversible equilibrium as with esters.
  • Acetals are used as protecting groups for carbonyl groups in organic synthesis because they are stable with respect to hydrolysis by bases and with respect to many oxidizing and reducing agents.
  • Examples of acetals include: Dioxolane, Metaldehyde, Paraldehyde, 1,3,5-Trioxane, Benzylidene etc.

What Is Hemiacetal?

hemiacetal or a hemiketal is a compound that results from the addition of an alcohol to an aldehyde or a ketone, respectively. The Greek word hèmi, meaning half, refers to the fact that a single alcohol has been added to the carbonyl group, in contrast to acetals or ketals, which are formed when a second alkoxy group has been added to the structure.

The general formula of a hemiacetal is R1R2C(OH)OR, where R1 or R2 is often hydrogen and R (bonded to O) is not hydrogen.
While in the IUPAC definition of a hemiacetal R1 or R2 may or may not be a hydrogen, in a hemiketal none of the R-groups can be a hydrogen. Hemiketals are regarded as hemiacetals where none of the R-groups are H, and are therefore a subclass of the hemiacetals.

Hemiacetals and hemiketals are generally not stable compounds. In some cases however, stable cyclic hemiacetals and hemiketals, called lactols, can be readily formed, especially with 5- and 6-membered rings. In this case an intramolecular OH group reacts with the carbonyl group. Glucose and many other aldoses exist as cyclic hemiacetals whereas fructose and similar ketoses exist as cyclic hemiketals.

What You Need To Know About Hemiacetal

  • Hemiacetal is a carbon connected to two oxygen atoms, where one oxygen is an alcohol (OH) and the other is an ether (OR).
  • The general formula for a hemiacetal is given as RHC(OH)OR’.
  • Hemiacetal is formed as an intermediate that results from the addition of an alcohol to an aldehyde or a ketone.
  •  Hemiacetal is less stable when compared to an acetal.
  • A hemiacetal can react with an alcohol under acidic conditions to form an acetal and can dissociate to form an aldehyde and an alcohol.
  • The simplest hemiacetal is 1-methoxyethan-1-ol
  • It is important to note that a hemiacetal is formed as an intermediate during the formation of an acetal.

Also Read: Difference Between Epimers And Anomers

Difference Between Acetal And Hemiacetal In Tabular Form

BASIS OF COMPARISON ACETAL HEMIACETAL
Description Acetal is a group of atoms that is represented by a central carbon atom bonded to two-OR groups, -R group and a –H group.   Hemiacetal is a carbon connected to two oxygen atoms, where one oxygen is an alcohol (OH) and the other is an ether (OR).
Formula The general formula of an acetal can be given as RHC(OR’)2.   The general formula for a hemiacetal is given as RHC(OH)OR’.  
Formation Acetals are formed when aldehyde or ketone reacts with an alcohol in the presence of an acid catalyst. Hemiacetal is formed as an intermediate that results from the addition of an alcohol to an aldehyde or a ketone.  
Stability Hemiacetal is less stable when compared to an acetal.   Hemiacetal is less stable when compared to an acetal.  
Examples Dioxolane, Metaldehyde, Paraldehyde, 1,3,5-Trioxane, Benzylidene etc.   The simplest hemiacetal is 1-methoxyethan-1-ol.  

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