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How Are Ketones Acidic

Chapter 16: Aldehydes And Ketones (carbonyl Compounds)

Chapter 16: Aldehydes And Ketones (carbonyl Compounds)

The Carbonyl Double Bond Both the carbon and oxygen atoms are hybridized sp2, so the system is planar. The three oxygen sp2 AO’s are involved as follows: The two unshared electorn pairs of oxygen occupy two of these AO’s, and the third is involved in sigma bond formation to the carbonyl carbon. The three sp2 AO’s on the carbonyl carbon are involved as follows: One of them is involved in sigma bonding to one of the oxygen sp2 AO’s, and the other two are involved in bonding to the R substituents. The 2pz AO’s on oxygen and the carbonyl carbon are involved in pi overlap, forming a pi bond. The pi BMO, formed by positive overlap of the 2p orbitals, has a larger concentration of electron density on oxygen than carbon, because the electrons in this orbital are drawn to the more electronegative atom, where they are more highly stabilized. This result is reversed in the vacant antibonding MO. As a consequence of the distribution in the BMO, the pi bond (as is the case also with the sigma bond) is highly polar, with the negative end of the dipole on oxygen and the positive end on carbon. We will see that this polarity, which is absent in a carbon-carbon pi bond, has the effect of strongly stabilizing the C=O moiety. Resonance Treatment of the Carbonyl Pi Bond 1.Note that the ionic structure (the one on the right side) has one less covalent bond, but this latter is replaced with an ionic bond (electrostatic bond). 2.This structure is a relatively “good” one, therefore, and contributes extensively to the resonance hybrid, making this bond much more thermodynamically stable than the C=C pi bond, for which the corresponding ionic structure is much less favorable (negative charge is less stable on carbon than on oxygen). 3.The carbonyl carbon therefore has extensive car Continue reading >>

Ketones: Clearing Up The Confusion

Ketones: Clearing Up The Confusion

Ketones, ketosis, ketoacidosis, DKA…these are words that you’ve probably heard at one point or another, and you might be wondering what they mean and if you need to worry about them at all, especially if you have diabetes. This week, we’ll explore the mysterious world of ketones, including if and how they may affect you. Ketones — what are they? Ketones are a type of acid that the body can form if there’s not enough carbohydrate to be burned for energy (yes, you do need carbs for fuel). Without enough carb, the body turns to another energy source: fat. Ketones are made in the liver from fat breakdown. This is called ketogenesis. People who don’t have diabetes can form ketones. This might occur if a person does extreme exercise, has an eating disorder, is fasting (not eating), or is following a low-carbohydrate diet. This is called ketosis and it’s a normal response to starvation. In a person who has diabetes, ketones form for the same reason (not enough carb for energy), but this often occurs because there isn’t enough insulin available to help move carb (in the form of glucose) from the bloodstream to the cells to be used for energy. Again, the body scrambles to find an alternate fuel source in the form of fat. You might be thinking that it’s a good thing to burn fat for fuel. However, for someone who has diabetes, ketosis can quickly become dangerous if it occurs due to a continued lack of insulin (the presence of ketones along with “normal” blood sugar levels is not necessarily a cause for concern). In the absence of insulin (which can occur if someone doesn’t take their insulin or perhaps uses an insulin pump and the pump has a malfunction, for example), fat cells continue to release fat into the circulation; the liver then continues to churn Continue reading >>

What Is The Ph Of The Blood In A Diabetic Patient When His Glucose Levels Are Appropriate?

What Is The Ph Of The Blood In A Diabetic Patient When His Glucose Levels Are Appropriate?

Diabetes causes your body's pH levels to become more acidic and develop a condition called ketoacidosis, the American Diabetes Association explains. Your body's pH level refers to the acidity or alkalinity of the fluids in your body. Diabetes impairs your body's ability to properly utilize the glucose in your blood. Instead, your body is forced to convert fat into energy through a process that develops into ketoacidosis. Diagnosing ketoacidosis involves testing blood for the presence of ketones, the University of Maryland Medical Center explains. There are two main types of diabetes. Type 1 diabetes is congenital, and its symptoms appear as early as childhood, MayoClinic.com explains. Type 1 diabetes is characterized by your body's inability to produce insulin, the hormone needed for cells to metabolize glucose into energy. Type 2 diabetes is essentially defined by acquired insulin resistance that usually manifests in adulthood. Both types of diabetes cause increased thirst, frequent urination, unexplained weight loss, hypertension and ketoacidosis. Left untreated, both types of diabetes lead to complications that damage your cardiovascular system, kidneys and nerves due to the accumulated glucose in your blood. Complications due to diabetes such as ketoacidosis are fatal if not treated. Ketones are the acidic byproducts of fat breakdown that accumulate when your body uses fat instead of glucose as a source of fuel, MedlinePlus, a service of the National Institutes of Health, explains. As your ketone levels increase, your body becomes more acidic. Ketones are present in both types of diabetes but are generally more typical of type 1 diabetes. Ketones are also sometimes present in urine. Acetone and acetoacetic acid are examples of ketones. Ketoacidosis does not happen o Continue reading >>

Acidity Of

Acidity Of

a-Hydrogens In the following table, the acidity of the H for various enolate systems and other closely related systems are given. You should be able to justify the trends in this data ! Why are the protons adjacent to carbonyl groups acidic ? As we have advocated before, look at the stabilisation of the conjugate base. Notice the proximity of the adjacent p system, and hence the possibility for RESONANCE stabilisation by delocalisation of the negative charge to the more electronegative oxygen atom. The more effective the resonance stabilisation of the negative charge, the more stable the conjugate base is and therefore the more acidic the parent system. Let's compare pKa of the common systems: aldehyde pKa = 17, ketone pKa = 19 and an ester pKa = 25, and try to justify the trend. The difference between the 3 systems is in the nature of the group attached to the common carbonyl. The aldehyde has a hydrogen, the ketone an alkyl- group and the ester an alkoxy- group. H atoms are regarded as having no electronic effect : they don't withdraw or donate electrons. Alkyl groups are weakly electron donating, they tend to destabilise anions (you should recall that they stabilise carbocations). This is because they will be "pushing" electrons towards a negative system which is unfavourable electrostatically. Hence, the anion of a ketone, where there are extra alkyl groups is less stable than that of an aldehyde, and so, a ketone is less acidic. In the ester, there is also a resonance donation from the alkoxy group towards the carbonyl that competes with the stabilisation of the enolate charge. This makes the ester enolate less stable than those of aldehydes and ketones so esters are even less acidic. The most important reactions of ester enolates are the Claisen and Dieckmann cond Continue reading >>

Ketosis

Ketosis

Tweet Ketosis is a state the body may find itself in either as a result of raised blood glucose levels or as a part of low carb dieting. Low levels of ketosis is perfectly normal. However, high levels of ketosis in the short term can be serious and the long term effects of regular moderate ketosis are only partially known at the moment. What is ketosis? Ketosis is a state the body goes into if it needs to break down body fat for energy. The state is marked by raised levels of ketones in the blood which can be used by the body as fuel. Ketones which are not used for fuel are excreted out of the body via the kidneys and the urine. Is ketosis the same as ketoacidosis? There is often confusion as to the difference between ketosis and ketoacidosis. Ketosis is the state whereby the body is producing ketones. In ketosis, the level of ketones in the blood can be anything between normal to very high. Diabetic ketoacidosis, also known as DKA, only describes the state in which the level of ketones is either high or very high. In ketoacidosis, the amount of ketones in the blood is sufficient to turn the blood acidic, which is a dangerous medical state. When does ketosis occur? Ketosis will take place when the body needs energy and there is not sufficient glucose available for the body. This can typically happen when the body is lacking insulin and blood glucose levels become high. Other causes can be the result of being on a low carb diet. A low level of carbohydrate will lead to low levels of insulin, and therefore the body will produce ketones which do not rely on insulin to get into and fuel the body’s cells. A further cause of ketosis, less relevant to people with diabetes, is a result of excessive alcohol consumption. Is ketosis dangerous? The NHS describes ketosis as a pote Continue reading >>

Aldehydes, Ketones, Carboxylic Acids, And Esters

Aldehydes, Ketones, Carboxylic Acids, And Esters

Learning Objectives By the end of this section, you will be able to: Describe the structure and properties of aldehydes, ketones, carboxylic acids and esters Another class of organic molecules contains a carbon atom connected to an oxygen atom by a double bond, commonly called a carbonyl group. The trigonal planar carbon in the carbonyl group can attach to two other substituents leading to several subfamilies (aldehydes, ketones, carboxylic acids and esters) described in this section. Aldehydes and Ketones Both aldehydes and ketones contain a carbonyl group, a functional group with a carbon-oxygen double bond. The names for aldehyde and ketone compounds are derived using similar nomenclature rules as for alkanes and alcohols, and include the class-identifying suffixes –al and –one, respectively: In an aldehyde, the carbonyl group is bonded to at least one hydrogen atom. In a ketone, the carbonyl group is bonded to two carbon atoms: In both aldehydes and ketones, the geometry around the carbon atom in the carbonyl group is trigonal planar; the carbon atom exhibits sp2 hybridization. Two of the sp2 orbitals on the carbon atom in the carbonyl group are used to form σ bonds to the other carbon or hydrogen atoms in a molecule. The remaining sp2 hybrid orbital forms a σ bond to the oxygen atom. The unhybridized p orbital on the carbon atom in the carbonyl group overlaps a p orbital on the oxygen atom to form the π bond in the double bond. Like the C=O bond in carbon dioxide, the C=O bond of a carbonyl group is polar (recall that oxygen is significantly more electronegative than carbon, and the shared electrons are pulled toward the oxygen atom and away from the carbon atom). Many of the reactions of aldehydes and ketones start with the reaction between a Lewis base and Continue reading >>

Organic Chemistry/ketones And Aldehydes

Organic Chemistry/ketones And Aldehydes

Aldehydes () and ketones () are both carbonyl compounds. They are organic compounds in which the carbonyl carbon is connected to C or H atoms on either side. An aldehyde has one or both vacancies of the carbonyl carbon satisfied by a H atom, while a ketone has both its vacancies satisfied by carbon. 3 Preparing Aldehydes and Ketones Ketones are named by replacing the -e in the alkane name with -one. The carbon chain is numbered so that the ketone carbon, called the carbonyl group, gets the lowest number. For example, would be named 2-butanone because the root structure is butane and the ketone group is on the number two carbon. Alternatively, functional class nomenclature of ketones is also recognized by IUPAC, which is done by naming the substituents attached to the carbonyl group in alphabetical order, ending with the word ketone. The above example of 2-butanone can also be named ethyl methyl ketone using this method. If two ketone groups are on the same structure, the ending -dione would be added to the alkane name, such as heptane-2,5-dione. Aldehydes replace the -e ending of an alkane with -al for an aldehyde. Since an aldehyde is always at the carbon that is numbered one, a number designation is not needed. For example, the aldehyde of pentane would simply be pentanal. The -CH=O group of aldehydes is known as a formyl group. When a formyl group is attached to a ring, the ring name is followed by the suffix "carbaldehyde". For example, a hexane ring with a formyl group is named cyclohexanecarbaldehyde. Aldehyde and ketone polarity is characterized by the high dipole moments of their carbonyl group, which makes them rather polar molecules. They are more polar than alkenes and ethers, though because they lack hydrogen, they cannot participate in hydrogen bonding like Continue reading >>

Acid-catalysed Bromination Of Ketones

Acid-catalysed Bromination Of Ketones

Click the structures and reaction arrows in sequence to view the 3D models and animations respectively Bromination of ketones occurs smoothly with bromine in acetic acid. The first step occurs in a cyclic way resulting in protonation of the carbonyl and formation of the enol occuring at the same time. The next step is the attack of the enol on the bromine. The proton on the carbonyl is then lost to yield bromoacetone. M. F. Ruasse, in Advances in Physical Organic Chemistry, 1993, vol. 28, pp. 207–291. 461 1085 Continue reading >>

The Many Benefits Of Ketosis

The Many Benefits Of Ketosis

Along with living an alkaline lifestyle, one of the key principles of my Magic Menopause hormone reset program is eating a ketogenic-friendly diet. This diet puts your body in a fat-burning state called ketosis. My program’s Keto-Alkaline™ Diet includes ketogenic methodologies. It also incorporates the “reality of everyday life” into one’s diet. I’ll explain what I mean about this in just a moment. First, for those of you who aren’t familiar with ketosis, let me give you a short overview. A ketogenic diet is a diet which is low in (unhealthy) carbs and high in (healthy) fats and (healthy) protein. So how does a ketogenic diet work so well at supporting fat loss and other health benefits? It’s really a simple concept at the surface, a bit more complex when you look at the actual physiology. Ketosis is all about what your body uses as fuel. Eating high carbs = high blood glucose (sugar), high insulin, stored fat… and low fat burning, low metabolism and belly fat. Your body’s fuel source is glucose, not fat. Let me explain. When you eat carbs your body’s blood glucose increases and spikes your blood sugar. Your body releases more insulin as a reaction to elevated blood glucose levels. Insulin is produced to get the glucose from your body and into the cells. There it gets converted to energy. Your body burns the glucose to make its energy and then insulin tells the cells to store their energy as carbs or fat (the unhealthy and dreaded belly fat). When you eat a lot of carbs on an ongoing basis (like many Americans do, eating a lot of processed foods, sugar, alcohol, soda and such!) insulin is continually stimulated. This can lead to a health condition called insulin resistance, where the cells start to resist the insulin. When this happens, your blood Continue reading >>

The Alkaline Diet Vs Acidic Ketones

The Alkaline Diet Vs Acidic Ketones

Whether you think eating alkaline foods is useful or woo woo junk it appears that metabolic acidosis is a thing. Metabolic acidosis seems to be interrelated with insulin resistance, Type 2 Diabetes, and retention of muscle mass. To prevent metabolic acidosis, it appears prudent to ensure that your body has adequate minerals to enable your kidneys to balance pH over the long term. This can be achieved by eating plenty of veggies and/or supplementing with alkaline minerals (e.g. magnesium, sodium, potassium, zinc etc). If you eat plenty of veggies you’re probably getting enough alkalising minerals, however, you can easily test your urine to see if your dietary acid load is high. If you are targeting a high fat therapeutic ketogenic diet, following a zero-carb dietary approach and/or taking exogenous ketones it seems then it may be even more important to be mindful of your acid load and consider mineral supplementation. Recently I had a fascinating, surprising and exciting experience during a fast. The chart below shows my ketones, glucose and ‘total energy’ (i.e. glucose plus ketones) over the seven days. My ketones increased to above 8.0 mmol/L. They even couldn’t be read on my ketone metre! It was the full keto brochure experience. It was like my body fat was effortlessly feeding my brain with delicious, succulent ketones! I felt great. This chart shows my glucose : ketone index (GKI) dropping to below 0.5 after a few days. The orange dots in this chart shows the relationship between glucose and ketones about 18 months ago when I first started trying this keto thing (after I read ‘Jimmy’s Moore’s Keto Clarity’). The blue dots show the relationship between my glucose and ketones during the recent fast. As you can see from the much flatter line, my blood g Continue reading >>

Ketone Bodies

Ketone Bodies

Ketone bodies Acetone Acetoacetic acid (R)-beta-Hydroxybutyric acid Ketone bodies are three water-soluble molecules (acetoacetate, beta-hydroxybutyrate, and their spontaneous breakdown product, acetone) that are produced by the liver from fatty acids[1] during periods of low food intake (fasting), carbohydrate restrictive diets, starvation, prolonged intense exercise,[2], alcoholism or in untreated (or inadequately treated) type 1 diabetes mellitus. These ketone bodies are readily picked up by the extra-hepatic tissues, and converted into acetyl-CoA which then enters the citric acid cycle and is oxidized in the mitochondria for energy.[3] In the brain, ketone bodies are also used to make acetyl-CoA into long-chain fatty acids. Ketone bodies are produced by the liver under the circumstances listed above (i.e. fasting, starving, low carbohydrate diets, prolonged exercise and untreated type 1 diabetes mellitus) as a result of intense gluconeogenesis, which is the production of glucose from non-carbohydrate sources (not including fatty acids).[1] They are therefore always released into the blood by the liver together with newly produced glucose, after the liver glycogen stores have been depleted (these glycogen stores are depleted after only 24 hours of fasting)[1]. When two acetyl-CoA molecules lose their -CoAs, (or Co-enzyme A groups) they can form a (covalent) dimer called acetoacetate. Beta-hydroxybutyrate is a reduced form of acetoacetate, in which the ketone group is converted into an alcohol (or hydroxyl) group (see illustration on the right). Both are 4-carbon molecules, that can readily be converted back into acetyl-CoA by most tissues of the body, with the notable exception of the liver. Acetone is the decarboxylated form of acetoacetate which cannot be converted Continue reading >>

Ketone

Ketone

Not to be confused with ketone bodies. Ketone group Acetone In chemistry, a ketone (alkanone) /ˈkiːtoʊn/ is an organic compound with the structure RC(=O)R', where R and R' can be a variety of carbon-containing substituents. Ketones and aldehydes are simple compounds that contain a carbonyl group (a carbon-oxygen double bond). They are considered "simple" because they do not have reactive groups like −OH or −Cl attached directly to the carbon atom in the carbonyl group, as in carboxylic acids containing −COOH.[1] Many ketones are known and many are of great importance in industry and in biology. Examples include many sugars (ketoses) and the industrial solvent acetone, which is the smallest ketone. Nomenclature and etymology[edit] The word ketone is derived from Aketon, an old German word for acetone.[2][3] According to the rules of IUPAC nomenclature, ketones are named by changing the suffix -ane of the parent alkane to -anone. The position of the carbonyl group is usually denoted by a number. For the most important ketones, however, traditional nonsystematic names are still generally used, for example acetone and benzophenone. These nonsystematic names are considered retained IUPAC names,[4] although some introductory chemistry textbooks use systematic names such as "2-propanone" or "propan-2-one" for the simplest ketone (CH3−CO−CH3) instead of "acetone". The common names of ketones are obtained by writing separately the names of the two alkyl groups attached to the carbonyl group, followed by "ketone" as a separate word. The names of the alkyl groups are written alphabetically. When the two alkyl groups are the same, the prefix di- is added before the name of alkyl group. The positions of other groups are indicated by Greek letters, the α-carbon being th Continue reading >>

Why Are Aldehydes And Ketones Neutral And Not Acidic/basic?

Why Are Aldehydes And Ketones Neutral And Not Acidic/basic?

This question is quite general, and as other answers have pointed out, depends on what you mean by acidic/basic. The other answers have already covered the Lewis bit, so I will focus a bit more on the Bronsted-Lowry and Arrhenius definitions. In water, almost all aldehydes and ketones do not dissociate to give the H+ or OH- ion, which is the Arrhenius definition. However, the alpha position of acetylacetone is considered acidic by the Bronsted-Lowry definition, and can be deprotonated by strong bases to give the conjugated enone after tautomerism. This is due to the stability of the conjugate base. Continue reading >>

Urine Tests For Diabetes: Glucose Levels And Ketones

Urine Tests For Diabetes: Glucose Levels And Ketones

The human body primarily runs on glucose. When your body is low on glucose, or if you have diabetes and don’t have enough insulin to help your cells absorb the glucose, your body starts breaking down fats for energy. Ketones (chemically known as ketone bodies) are byproducts of the breakdown of fatty acids. The breakdown of fat for fuel and the creation of ketones is a normal process for everyone. In a person without diabetes, insulin, glucagon, and other hormones prevent ketone levels in the blood from getting too high. However, people with diabetes are at risk for ketone buildup in their blood. If left untreated, people with type 1 diabetes are at risk for developing a condition called diabetic ketoacidosis (DKA). While rare, it’s possible for people with type 2 diabetes to experience DKA in certain circumstances as well. If you have diabetes, you need to be especially aware of the symptoms that having too many ketones in your body can cause. These include: If you don’t get treatment, the symptoms can progress to: a fruity breath odor stomach pain trouble breathing You should always seek immediate medical attention if your ketone levels are high. Testing your blood or urine to measure your ketone levels can all be done at home. At-home testing kits are available for both types of tests, although urine testing continues to be more common. Urine tests are available without a prescription at most drugstores, or you can buy them online. You should test your urine or blood for ketones when any of the following occurs: Your blood sugar is higher than 240 mg/dL. You feel sick or nauseated, regardless of your blood sugar reading. To perform a urine test, you urinate into a clean container and dip the test strip into the urine. For a child who isn’t potty-trained, a pa Continue reading >>

Ketosis

Ketosis

There is a lot of confusion about the term ketosis among medical professionals as well as laypeople. It is important to understand when and why nutritional ketosis occurs, and why it should not be confused with the metabolic disorder we call ketoacidosis. Ketosis is a metabolic state where the liver produces small organic molecules called ketone bodies. Most cells in the body can use ketone bodies as a source of energy. When there is a limited supply of external energy sources, such as during prolonged fasting or carbohydrate restriction, ketone bodies can provide energy for most organs. In this situation, ketosis can be regarded as a reasonable, adaptive physiologic response that is essential for life, enabling us to survive periods of famine. Nutritional ketosis should not be confused with ketoacidosis, a metabolic condition where the blood becomes acidic as a result of the accumulation of ketone bodies. Ketoacidosis can have serious consequences and may need urgent medical treatment. The most common forms are diabetic ketoacidosis and alcoholic ketoacidosis. What Is Ketosis? The human body can be regarded as a biologic machine. Machines need energy to operate. Some use gasoline, others use electricity, and some use other power resources. Glucose is the primary fuel for most cells and organs in the body. To obtain energy, cells must take up glucose from the blood. Once glucose enters the cells, a series of metabolic reactions break it down into carbon dioxide and water, releasing energy in the process. The body has an ability to store excess glucose in the form of glycogen. In this way, energy can be stored for later use. Glycogen consists of long chains of glucose molecules and is primarily found in the liver and skeletal muscle. Liver glycogen stores are used to mai Continue reading >>

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