functional groups in aspirin functional groups in aspirin

identify the functional groups present in an organic compound, given its structure. from how I drew it up here but it doesn't really matter, and then I'll put in our Because Aspirin is a non- selective COX- 1 and COX-2 inhibitor, as well as its beneficial analgesic, anti-inflammatory, anti-platelet and antipyretic effects its use can also result in peptic ulcer development and gastric bleeding. Which of the following compounds are esters? Some of the important functional groups in . It takes about 48 hours to excrete an aspirin completely. Identify the functional groups in the following molecules: Identify the functional groups present in the given . You can use willow bark to make aspirin. Aspirin is only slightly soluble in water, so if we add it to the reaction mixture, the product would rather clump together than be in the water phase. Prostaglandins are found throughout the body and are made to help manage injury or infection. In an acyl phosphate, the carbonyl carbon is bonded to the oxygen of a phosphate, and in an acid chloride, the carbonyl carbon is bonded to a chlorine. 3 67 LEARNING OBJECTIVES After completing this chapter, students will be able to: Identify the following acidic functional groups: carboxylic acids, -dicarbonyls, Full Professor of Medicine, Universidad de Buenos Aires, Argentina So again, this difference is subtle, but it's important, and a So this is a carboxylic acid. Would I be correct to describe geraniol as 2 isoprene units and an alcohol? 3. 26, 27 The luminescence of these complexes arises from the sensitization of Ln(III) ions, and this indirect excitation by the surrounding ligands is known as the . Iodine has The four types of alcohol are ethyl, denatured, isopropyl and rubbing. Professor of Oncology and Clinical Trials, MRC Programme Leader and Chair of the Cancer Group, MRC Clinical Trials Unit at UCL, honorary consultant in medical oncology at the Brighton and Sussex University Hospital. - Definition, Uses & Types, How Does Aspirin Work? Acetylsalicylic acid contains an ester and acetyl functional groups, therefore giving it a larger mass than salicylic acid. They are assigned priorities based broadly on their reactivity. 3. The common name of aspirin is acetylsalicylic acid and its IUPAC name is 2-Acetoxybenzoic acid. If the central carbon in an alcohol is bonded to only one other carbon, we call the group a primary alcohol. Heptane Formula, Structure & Uses | What is Heptane? Is an isoprene ever a functional unit? I have fulfilled these appointments in settings of vital social engagement and impact, most notably at the Hospital de Clnicas Jos de San Martn of the Universidad de Buenos Aires, a public hospital with high academic recognition. | Urea Molecular Structure & Formula. What is N-(2,2,2-Trichloroethyl)carbonyl] Bisnor-(cis)-tilidine's functional group? Aspirin inhibits the production of thromboxane A2 (TXA2) by stopping the conversion of arachidonic acid to TXA2. But at a higher temperature, such as 70 degrees Celsius, it would take less than 10 hours for all of the aspirin to be degraded. Finally, let's look at one giant compound with lots of different functional groups, and let's see if we can identify But this nitrogen is right next to a carbonyl, so it's not an amine. Create your account, 5 chapters | Activity 2 Let's first take note of the ester on aspirin: This reaction occurs on the ester, so for simplicity's sake, we will refer to the benzene group as 'R1' and the methane group as 'R2': Let's first go through the mechanism under acidic conditions. Direct link to Callum Budge's post Hi, just out of curiosity, Posted 8 years ago. Hydrolysis really just means a chemical reaction between a compound and water, which results in the breakdown of that compound. All rights reserved. Is it only the alkenes, alkynes, and the rest? 57 lessons. What is a functional group? Aspirin is an approximately 150- to 200-fold more potent inhibitor of the (constitutive) isoform of the platelet enzyme (COX-1) than the (inducible) isoform (COX-2) which is expressed by cytokines, inflammatory stimuli, and some growth factors. So hopefully you see the difference there. Direct link to Kaleb Asnake's post Hi, when we name the simp, Posted a year ago. 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Acetylsalicylic acid has both anti-inflammatory and antipyretic effects. Aspirin is prepared by chemical synthesis from salicylic acid, through acetylation with acetic anhydride. Please fill in the form below and we will contact you with further information. This answer is: Study guides. Identify the functional groups in each molecule. Acetylation Reaction | What is Acetylation? The non-steroidal anti-inflammatory drugs. Prof. Ge has been engaged in clinical and scientific research work of cardiovascular disease since 1987, and his research area covers the pathogenesis of coronary heart disease, early diagnosis and treatment plan optimization. The reaction occurs at the ester with the water or hydroxy group attacking the carbonyl and then the alcohol, or salicylic acid, can act as a leaving group. The transfer of the proton to the substrate occurs in the transition state of the reaction. Some content on this page could not be displayed. So for example a carboxylic acid will have a higher priority than an alkene or alkyne. It contains polar functional groups which can form hydrogen bonds with polar water molecules. The functional groups present in caffeine are amines, amides and an alkene group. Another way of thinking of an ester is that it is a carbonyl bonded to an alcohol. Acetylsalicylic acid (ASA) is a commonly used drug for the treatment of pain and fever due to various causes. Answer (1 of 5): It has two functional group one is acid(cooh) and the other is phenolic oh group.. the rest of the molecule over here on the other side, so now this is an ether. As a member, you'll also get unlimited access to over 88,000 AACR Honors Dr. Andrew T. Chan With 2019 AACR-Waun Ki Hong Award. Consider the first step in the base catalyzed hydrolysis of aspirin shown below; Which of the following is the structure of the intermediate formed in this step? Paracetamol (acetaminophen) is an aromatic compound containing an OH (hydroxyl) functional group and a HN-CO-R functional group. Functional groups are atoms or small groups of atoms (two to four) that exhibit a characteristic reactivity. Ionic salts of aspirin, such as sodium acetylsalicylate, are more soluble in water since they form stronger ion-dipole interactions with water. So this is a ketone and an amine. Which of the atoms labeled 1-4 is an electrophile? And what would this one be? I received consultant and speakers fees from Acticor Biotech, Amgen, Bayer, GlaxoSmithKline, Tremeau, Zambon. When the aspirin enters the stomach, some of it absorbs within the stomach. Draw the structures of the products of the acid catalyzed hydrolysis of each of the following esters. Functional groups have different priorities when it comes to naming. So when you have a carbonyl and an R group on one side, an R group on the other side, they could be the same R group, they could be a different R group. First, the carbonyl, or the carbon double bonded to the oxygen, is made into a really strong electrophile, or electron deficient atom, by adding a hydrogen to the oxygen: Now that the carbonyl is a good electrophile, the electrons from the oxygen on water can attack: Then a proton transfer occurs in order to make the alcohol with R1 a good leaving group: The electrons from the oxygen are pushed back onto the carbonyl, which pushes off the alcohol attached to R1, since that is now a good leaving group: So at this point, we have our first product, salicylic acid. Practice #2. Alkanes, cycloalkanes, and functional groups, Creative Commons Attribution/Non-Commercial/Share-Alike. When the esterification reaction is complete, water will be added to the mixture. Peak concentration of salicylate in the plasma occurs approximately 1-2 hours after ingestion. This explains the different dosage requirements of aspirin as an antithrombotic (COX-1) and an anti . Aspirin: Structure, Molecular Weight & Functional Group, Hydrolysis of Acetanilide: Mechanism & Explanation, Aspirin: Pharmacokinetics & Pharmacodynamics, Acetic Anhydride | Formula, Density & Uses, Ester Hydrolysis Mechanism & Steps | Acid-Catalyzed vs. Base-Catalyzed. He is also the designate chairman of the Cardiovascular Disease Branch of Chinese Medical Association, council member of the Cardiovascular Angiography and Interventions Association, international consultant of the American Heart Association. groups, and how functional groups can be altered to provide a therapeutic benefit. Here's another alkene, right, here's another carbon-carbon double bond. Enrolling in a course lets you earn progress by passing quizzes and exams. Well, here is an aromatic ring. I think its because we set the alkanes as the reference and most simple type of organic compound. Direct link to alina's post What does the benz- in be, Posted 7 years ago. A functional group is a specific group of atoms within a molecule that gives rise to the characteristic chemical reactions of the molecule. Zero-Order Kinetics Equation & Examples | What is Zero-Order Kinetics? She has taught Organic and Inorganic Chemistry at the Undergraduate and Master Level. Functional Groups in Organic Molecules | Overview, List & Examples, Sulfonamide: Chemical Structure & Derivatives, Acetylation of Ferrocene | Mechanism, Equation & Major Product, Caffeine Structure, Formula & Composition | Caffeine Molecule. difference between an amide and an amine. All three compounds are aromatic. Cox-1 has a protective role for the stomach lining and COX-2 is involved in pain and inflammation. Below are the line and Lewis structures of diethyl ether, a common laboratory solvent and also one of the first medical anaesthesia agents. At higher pH, in the intestine (pH = 6), a greater proportion of aspirin is ionized, so it moves across membranes more slowly. What functional groups are present in aspirin? So this is a heart medication. The fascinating emission can be attained through careful design or by selecting an appropriate organic chromophore that may shield the coordination shell from deactivating moieties and serve as an efficient antenna molecule. We have already seen the simplest possible example of an alcohol functional group in methanol. The neutralization reaction can be used to determine the amount of aspirin (acetylsalicylic acid) present in commercially available aspirin tablets using a back (indirect) titration method. Now that you are familiar with the mechanism of the hydrolysis of aspirin the following activities are designed to deepen your understanding of the mechanism and apply the knowledge to the hydrolysis of other esters. All other trademarks and copyrights are the property of their respective owners. It is tempting to call it an alcohol group. We have an oxygen, and that oxygen is directly It is also referred to as a R-OCO-R' group. Explore the structure, molecular weight, and the three functional groups of aspirin. Molecules with carbon-nitrogen double bonds are called imines, or Schiff bases. The name "Ibuprofen" comes from its old chemical structure name: iso-butyl-propanoic-phenolic acid. ]aS-.Nkq?O9 qX So now the carbonyl is gone, and now we do have an ether. If the carbon of an alkane is bonded to a halogen, the group is now referred to as a haloalkane (fluoroalkane, chloroalkane, etc.). Practice #1. :-). hydrogen directly bonded to our carbonyl carbon, that is an aldehyde. Phenol C6H5-OHSodium Hydroxide NaOHCarbon Dioxide CO2Acetic Anhydride CH3COOCOCH3Hydrogen H. The ReactionsThe production of aspirin from raw materials can be divided into four separate reactions as shown here: 1. As we progress in our study of organic chemistry, it will become extremely important to be able to quickly recognize the most common functional groups, because they are the key structural elements that define how organic molecules react. What about ethane? Functional groups are structural units within organic compounds that are defined by specific bonding arrangements between specific atoms. a. ether, ketone, and carboxylic acid b. carboxylic acid and ester c. ester and phenol d. carboxylic acid and ketone Functional Group: Organic. When people are in pain, they want to ensure that the pain medication will work as needed. Functional groups have different priorities when it comes to naming. Acetylsalicylic acid. Ready to test your skills? giveaway as to the functional group, we're talking I found out that aspirin's systematic name is 2-acetyloxybenzoic acid. So in all of the molecules, are the single bonds, or alkanes, not considered a functional group? bonded to an oxygen, so let's write this out. look at this oxygen here, and say, okay, I have an oxygen, and then I have an R group on one side, and I have an R group on the other side. Explore the structure, molecular weight, and the three functional. Match the pK a values provided to the appropriate functional groups and identify if the functional group is acidic or basic. In the synthesis reaction of aspirin, the salicylic acid is the limiting reactant and the acetic anhydride is in excess. about an aldehyde here. Figure 2. If so is that the reason carboxylic acids are considered so different to alcohols? One of the most important properties of amines is that they are basic, and are readily protonated to form ammonium cations. This one is a carboxylic acid, and this one is a ketone and an alcohol. explain why the properties of a given organic compound are largely dependent on the functional group or groups present in the compound. The nitrogen in an amide can be bonded either to hydrogens, to carbons, or to both. << /Length 5 0 R /Filter /FlateDecode >> that we've talked about in the previous videos. Hence, in aspirin carboxylic acid is the principal functional group. I received consultant and speaker fees Bayer. NSAIDs are typically divided into groups based on their chemical structure and selectivity: acetylated salicylates (aspirin), non-acetylated salicylates (diflunisal, salsalate), propionic acids (naproxen, ibuprofen, acetic acids (diclofenac, indomethacin), enolic acids (meloxicam, piroxicam) anthranilic acids (meclofenamate, mefenamic acid), For now, we will only worry about drawing and recognizing each functional group, as depicted by Lewis and line structures. When it reacts with water, we end up with two products, salicylic acid and acetic acid. John Chia MBBS (Spore), MRCP (UK), FAMS (Spore), Lina Badimon BSc, PharmD, PhD, FESC, FAHA. Methanol, of course, is in class by itself in this respect. However, this reaction is slow and has a relatively low yield. Salicylamide. then we have an R group on one side, R group on the other side, that is a ketone. Aspirin is an oral non-steroidal anti-inflammatory drug (NSAID) that is rapidly absorbed from the stomach and the small intestine. Nonsense Mutation Overview & Examples | What is a Nonsense Mutation? Make certain that you can define, and use in context, the key term below. An error occurred trying to load this video. But we do still see a hydrogen transfer from the acetic acid to the salicylic acid: Let's briefly review. Finally, in a nitrile group, a carbon is triple-bonded to a nitrogen. Plus, get practice tests, quizzes, and personalized coaching to help you The mobile phase is the solvent which slowly rises because of the capillary action and polarity. represent an ether, however, we have this carbonyl here. 2. Natamycin O OH OH CH 3 OH NH 2 HO O O H 3C OO O OH COOH a. We have an OH and then we have the rest of the molecule, so we have ROH. Hydrocarbon functional groups, like alkenes and alkynes, are only able to have LDF. Chapter 11 Anti-inflammatory drugs: treatment of arthritis and gout. Aspirin can displace drugs from their plasma binding-sites and in this way may increases the effects of anticoagulant drugs and oral hypoglycaemics. what wil be the systematic name for glucose that is C6H12O6, (2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanal, What does the benz- in benzaldehyde stand for? Phenol Group, Structure, Uses & Formula | What is Phenol? So here's a carbon double an amide, or an "amid", so make sure to know the RO, C double bond O, R, is an ester. difference between these. Thanks for A2A.. Organic Chemistry Functional Groups Quick Introduction of Structures 1 Answer Bio Feb 7, 2016 Ester Carboxylic acid Benzene Explanation: The benzene is not circled but you can see it there. It helped me pass my exam and the test questions are very similar to the practice quizzes on Study.com. So this actually is an ether now, we have an oxygen, we have an R group on one side, and we have The polarity of a compound is determined by its functional groups and masses. As a control mechanism, they act locally at the site of synthesis which limits the extent of their activity. Well here is a carbon-carbon double bond, and we know that a That's right! In this way aspirin can help lower the risk of future myocardial infarction (MI) or stroke1,3. Aspirin is a pain reliever and fever reducer, but if it's allowed to react with water then it can undergo hydrolysis, forming salicylic acid and acetic acid, which is no longer effective. Aspirin is a non-steroidal anti-inflammatory drug used for things like pain relief and lowering the risk of a heart attack. Drugs do not cross biological membranes when they are ionized. Decane Formula, Uses, & Structure | What is Decane? % This is an amine. prime drawn for that. The half-life of aspirin in the blood stream is 13-19 minutes and the half-life of its metabolite salicylate is around 3.5-4.5 hours. Sign up to be part of the aspirin community and be the first to receive latest information. The fact that COX-1 and COX-2 enzymes have different levels of sensitivity to aspirin and recover their cyclooxygenase activity post aspirin at different rates helps explain the different dosing regimens for aspirins varying clinical indications1. Between ester and carboxylic acid functional groups the highest priority functional group is carboxylic acid. In order to complete the second product, acetic acid, the hydrogen can be removed with a weak base: Under basic conditions we have a hydroxy group, which attacks the carbonyl. But since this oxygen is It also reacts with 3-methyl-2-pentene to form 2,3-dibromopentane. So let me go ahead and draw out another compound here, so we can see we have our NH2, and then we have our carbonyl. I feel like its a lifeline. All rights reserved. Thanks in advance! What about this one up here? Chloroform, CHCl3, is an example of a simple haloalkane. Aspirin, therefore, has an analgesic (reduces pain), anti-inflammatory (reduces redness and swelling), anti-platelet (reduces blood clots) and antipyretic (temperature reduction) effects1,2,3. to the carbonyl carbon. smart students mess up the difference between One of them is, students So ROH would be an alcohol. Direct link to skofljica's post (2R,3S,4R,5R)-2,3,4,5,6-P, Posted 7 years ago. Normal. Give it a shot to see where you stand. functional group a particular group of atoms that form the same structural pattern from one organic molecule to another ketone an organic compound containing a carbonyl group bonded to carbon atoms on both sides The structure of acetyl salicylic acid, or aspirin, is shown to the right. Here is that aromatic What functional groups are present in carbohydrates? In general, the presence of an oxygen is more polar . Chemical formula = C9H8O4 or CH3COOC6H4COOH or HC9H7O4. In sulfides, the oxygen atom of an ether has been replaced by a sulfur atom. we have an amine here. This in turn mediates aspirins effect of reduced inflammation and pain in affected tissues. Certain functional groups, like carboxylic acids and alcohols, have hydrogen-bonding abilities. The carbon atom labeled 2 is an electrophile. 2005 President, Sociedad Argentina de Cardiologa. Complete step-by-step answer: From the structure of aspirin it is clear that it contains two functional groups one is (carboxylic acid) and another is (ester). Ketones and aldehydes are two closely related carbonyl-based functional groups that react in very similar ways. So for example a carboxylic acid will have a higher priority than an alkene or alkyne. Just as there are primary, secondary, and tertiary alcohols, there are primary, secondary, and tertiary amines. 4844 views Aspirin is prepared by chemical synthesis from salicylic acid, through acetylation with acetic anhydride. Esterification & Reflux Purpose & Reaction | What is Reflux? Oxidation of Alcohols | Reagents, Mechanism & Reaction. It can also inhibit urate secretion and should be avoided in gout3. I have an interest in the design of large-scale trials and observational studies nested in large health care systems using big data analytic techniques. We do have a nitrogen with a lone pair of electrons on it, so it's tempting to say The functional groups shown here are found in many different biological molecules. Discover the aspirin synthesis reaction. - Definition, Causes & Purpose, What is Cardiac Ablation? Under room temperature conditions, it would take nearly a month for all of the aspirin to be degraded. All right, next we have a nitrogen with a lone pair of electrons. The benzene is not circled but you can see it there. Aspirin is a popular over-the-counter pain and fever reducer. Ronald received his PhD. ahead and write that out. Technically, he should have used the formula Ar-CHO. LEARNING OBJECTIVES After completing this chapter, students will be able to: 1. This will cause the precipitation of the acetylsalicylic acid and will react with any remaining acetic anhydride. Direct link to Ryan W's post The nitrogen of an amine , Posted a year ago. The exception to this definition is formaldehyde, in which the carbonyl carbon has bonds to two hydrogens. The male sex hormone testosterone contains ketone, alkene, and secondary alcohol groups, while acetylsalicylic acid (aspirin) contains aromatic, carboxylic acid, and ester groups. In these instances, aspirin generally acts on the symptoms of disease and does not modify or shorten the duration of a disease. All other trademarks and copyrights are the property of their respective owners. It is also called acetylsalicylic acid, derivative of salicylic acid, that is a mild nonnarcotic analgesic (pain reliever) useful in the relief of headache and muscle and joint aches. If we moved the OH further away, from the carbonyl, let's go ahead and draw one out like that. Prostaglandins upregulate the sensitivity of pain receptors. It is also used to help prevent heart attacks, strokes, and blood clot formation in people at risk of developing blood clots. with this compound. While not in any way a complete list, this section has covered most of the important functional groups that we will encounter in biological and laboratory organic chemistry. Steric hinderance effects. Aspirin (2-ethanoyloxybenzoic acid or acetylsalicylic acid) hydrolyses to produce 2-hydroxybenzoic acid and ethanoic acid. Its history dates back to ancient Greece, where an active ingredient in aspirin, called salicin, was found in willow bark. This was achieved by taking advantage of some fundamental organic chemistry. we know that's an ether. lessons in math, English, science, history, and more. In the past 3 years, I have received consultant fees from Tessa Therapeutics, Aslan Pharmaceuticals, Novartis, and AstraZeneca. The reason: an ester has replaced the acidic phenol in ASA. Entela Treska has a Master Degree in Teaching and Learning and a PhD in Chemistry. History shows that the use of aspirin dates back to 400 BC. Write structural formula(condensed) for all the primary , secondary and tertiary haloalkanes An alcohol has the molecular formula C4H10O write the structural formulae of the isomers to show See all questions in Quick Introduction of Structures. Phenol Properties, Synthesis & Reactions | What is Phenol? identify the functional groups present in each of the following compound types: alkenes, alkynes, arenes, (alkyl and aryl) halides, alcohols, ethers, aldehydes, ketones, esters, carboxylic acids, (carboxylic) acid chlorides, amides, amines, nitriles, nitro compounds, sulfides and sulfoxides. Aspirin can undergo hydrolysis, making it not as effective if it's exposed to water for extended periods of time. This table lists the locations and intensities of absorptions produced by typical functional groups. The IR spectrum of hexane. After completing this section, you should be able to. Taking aspirin and alcohol together can increase the risk of gastric bleeding 1,3. Create your account. Outside of its use for minor aches and pains, aspirin has proven to be an important therapeutic weapon in fighting heart attacks. So I'll first put in our ring, An aldehyde has a hydrogen directly bonded to this carbonyl carbon, but if there's no hydrogen, we're talking about a ketone here, so R, C double bond O, R, is a ketone. In comparison, the monoprotic acetylsalicylic acid (ASA, aspirin) is less acidic (pK a = 4.57). Try refreshing the page, or contact customer support. Below is a typical mechanism involving an un-dissociated acid (benzoic acid). The synthesis of aspirin is known in organic chemistry as an esterification reaction. Adjunct Associate Professor DUKE-NUS Graduate Medical School, Consultant Oncologist Curie Oncology Singapore, Visiting Consultant National Cancer Centre Singapore. bonded to a carbonyl, and then for this oxygen, we have the rest of the molecule so I received grant support as a principal investigator or co-investigator for research from the VA, DOD, NIH, Merck and Kowa. b. Aspirin Structural Formula The molecular geometry of aspirin is planar and its molecular mass is 180.159 g/mol. Qualitative analysis of the functional groups showed specific trends where the peak area increased with polarizability, electron density and decreased atomic radii. - Definition, Uses & Types, How Does Aspirin Work? Aspirin should not be used in children as it can produce a rare but dangerous Reyes syndrome resulting in coma and liver damage that can prove fatal1,3. The sulfur analog of an alcohol is called a thiol (the prefix thio, derived from the Greek, refers to sulfur). By Mike Bradley 12.21.2015. moles of aspirin used (relative molecular mass of aspirin = 180) and, therefore, the volume of 0.10 mol dm 3 sodium hydroxide solution needed to react with it in a 1:1 mole ratio. In an aldehyde, the carbonyl carbon is bonded on one side to a hydrogen, and on the other side to a carbon. Create your account, 17 chapters | To log in and use all the features of Khan Academy, please enable JavaScript in your browser. Let's go back and look at the chemical name of aspirin, acetylsalicylic acid. Your own medicine cabinet may contain a bottle of aspirin. Remember, before aspirin was officially discovered, Hippocrates used willow leaf tea, which contained the active ingredient salicin. So now we have an R group on one side, a carbonyl, and then another R group, so we have R, C double bond O, R, and that is a ketone. The OH functional group is called a phenol (pronounced fee-nol) group if it is joined to a benzene ring. Importantly, aspirin does not decrease normal body temperature1,2,3. Functional groups are specific groupings of atoms within molecules that have their own characteristic properties, regardless of the other atoms present in a molecule.