All About Amides

References

Reflection

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NamingQuiz

What is organic chemistry?

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Interesting facts

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Common uses

Impact on Environment

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impacT

Impact on Human Health

Chemical Reactions

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Properties

Physical Properties

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Standard nomenclature

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Background info

What is an amide?

All about amides

An amide is a functional group of organic compounds containing a carbonyl group (carbon double bonded to oxygen) and a nitrogen atom.

Organic chemistry studies the "structure, properties, composition, reactions, and preparation of organic compounds" (American Chemical Society, 2021). Organic compounds are compounds that contain carbon, most also including hydrogen. Any compounds with carbon and hydrogen are called hydrocarbons.

Organic Chemistry And Amides Background Information

Boiling Point

Melting Point

Solubility

Acid/ Base

State

Some properties briefly explained.

The boiling points of amides are pretty high when compared to other functional groups of a similar mass, such as alcohols (Libretexts, 2021). This is again due to the very high amounts of strong hydrogen bonds that require a lot of energy to dissipate. Additionally, amides are very polar (most polar among functional groups), giving them a higher boiling point due to the more energy needed to separate molecules with greater forces of attraction (between partially positively charged and negatively charged poles) (Ophardt, 2003).

Small amides (less than 5 carbon) are soluble in water. This is due to the strong polar attraction between the hydrogen of the amides and the water molecules (Cengage, 2014). Once chains get longer and the ends are further apart, the sites for this bonding to occur are less accessible due to the long carbon chain (Chemistry Dictionary, 2018). Additionally, polar dissolves polar and amides are very polar, which helps to explain their solubility (Ophardt, 2003).

There is no significant acidity/basicity - amides are generally considered neutral substances (Roberts & Caserio, 2021). Amides are neutral because the lone pair of electrons on the nitrogen atom is pulled into the carbonyl group, making Nitrogen unable to covalently bond with a hydrogen/ proton (Emily Learning, 2021). Although under normal conditions, amides act neutral, they can be made to act as either an acid or a base due to protonation (DeRuiter, 2005). Amides are less basic than amines, but esters, aldehydes, and ketones could be considered much less basic than amides (lisdbnet, 2021).

Overall, the melting points of amides are pretty high, primarily due to the powerful hydrogen bonds (there are many possibilities because of the presence of N and O bonded to H), which require a lot of energy to break (Viva, 2020). Primary amides have a higher melting point than secondary amides, which have a higher melting point than tertiary amides. This phenomenon occurs because as you add alkyl groups, you reduce the amount of hydrogen and the amount of hydrogen bonding possible (Cengage, 2014).

At room temperature, most amides are solids due to powerful intermolecular forces, specifically hydrogen bonding (Chemistry Dictionary, 2018). Methanamide is an exception to this rule as it is liquid at room temperature (Chemistry Dictionary, 2018).

All properties are general rules and there may be exceptions to some.

Physical Properties of Amides

Terminology

Hydrolysis Mechanism

Info

Protein Digestion and Synthesis

• Amide to Carboxylic Acid by Hydrolysis

• Amide to Nitriles by Dehydration

• Amide to Amine by Hydride Reduction

• Adding Carboxylic Acids and Amines using a dehydrating agent

• Adding Acid Anhydride + Amine by Nucleophillic Acyl substitution

• Partial hydrolysis of Nitriles

Decomposition Reactions

Synthesis Reactions

The chemical properties of Amides are fundamental in the survival of human beings and all living organisms. The chemical reactions undergone by and to amides, including synthesis and decomposition, are performed by living organisms daily to create and recycle proteins. Proteins are made from amide (peptide) bonds that bond together amino acids and are responsible for many biological processes such as DNA synthesis. Amides have a variety of uses in biology, including presence in antibiotics such as penicillin G (Kennepohl et al., 2021)

Chemical Properties

Ex: Kevlar & Nylon

Protein Formation

Ex: Penicilin

CO(NH2)2

HCON(CH₃)₂

C2H5NO

Structural Materials

Peptide Bonds

Drug Use

Urea

Dimethylformamide

Acetamide

Common Uses Of Amides

Suffix

Number

Prefix

Root

Speacial Cases

Learning Check

Step 1 - set up the naming process by identifying the longest consecutive carbon chain containing the amide functional group. Step 2 - List the branches in alphabetical order. Step 3 - given the number of carbon determined in step 1, add the correct root to the end of the last branch name. Step 4 - write the suffix 'amide' after the root name.

Write the suffix AMIDE after the root, connected to your root.

List branches in alphabetical order.

Given the number in step 1, use the following table to write the appropriate root.

Identify and number the longest consecutive chain of carbon that contains the functional group. Number it with a few rules in mind.

4 Easy Steps

Naming Amides (IUPAC)

Name the Amide

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Level 6

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Level 5

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Level 4

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Level 3

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Level 2

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Level 1

Other Toxic Amides

Acrylamide

Amides are also found in many molecules that are carcinogens or damage organs in the body. These particles damage cells' functions and may result in permanent damage.

Medical Impact

Negative

Reducing Acrylamide in Food

Health Impacts

Medical Impact - Specific Drugs

Amide groups are found in antibiotics such as penicillin G (or benzylpenicillin) and pain relievers such as tyneol. (Kennepohl et al. 2021) The variety of medical applications of amides helps keep us healthy.

Positive

PlasICS

Waste and Toxicity

Fertilizers

Food and Pollution

Environmental Impact

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Perfect Reactivity

02

01

Building Block of Life

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CIS AND TRANS ISOMERS

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Polyamide Waste

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ZWITTERIONIC RESONANCE STRUCTURE

About Amides

FunFacts!

Reflection

References

Hope you learned something about Amides!