A carbocation is formed on the original alkene (now alkane) in the more-substituted position, where the oxygen end of water attacks with its 4 non-bonded valence electrons (oxygen has 6 total valence electrons because it is found in Group 6 on the periodic table and the second row down: two electrons in a 2s-orbital and four in 2p-orbitals. ? If the steam is able to flow from the boiler at the same rate that it is produced, the addition of … Sulfuric acid (H 2 SO 4) reacts very vigorously with water in a highly exothermic reaction.If you add water to concentrated sulfuric acid, it can boil and spit and you may get a nasty acid burn. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. Once deprotinated, you have an enol, which then gets tautomerized. Addition of Water Alkenes can be converted to alcohols. This loss of excessive water is called guttation. Table salt is made of the ionic compound sodium chloride, which consists of the chemical elements sodium and chlorine.You probably learned from unintentional play at the kitchen table as a child that if you sprinkle salt into a glass of pure water, the salt disappears after a time; the more salt you add, the longer this takes, and it may require some shaking or stirring to bring about. Legal. Water is added to the pa‘i ‘ai during mashing, and again just before eating, to achieve the desired consistency, which can range from highly viscous to liquid. Practice with a molecular model kit and attempting the practice problems at the end can help eliminate any ambiguity. Alkenes undergo an addition reaction with water in the presence of a catalyst to form an alcohol. Once the hydrogen is bound you have a carbocation, which gets attacked by the water molecule. 3. Whether you add acid to the water or water to the acid is one of those things that's important to remember, but you may need to figure out. New York: W. H. Freeman and Company, 2007. This indicates that the product is a racemic mixture. forms. In general, whenever there is a change of state, such as the solid-liquid or the liquid-gas transition, heat energy can be added without a temperature change. All water additions shall be completed within 15 min. The goal is to produce water fit for specific purposes. from the start of the first water addition. The solid phase is known as ice and the gas phase is called steam. Vollhardt and Schore. Have questions or comments? If you take temperature readings while heating the ice in a pot on your stove, you find that the temperature of the ice begins to rise as the heat from the stove causes the ice particles to begin vibrating faster and faster. The belief that water was a fundamental substance persisted for more than 2,000 years until experiments in the second half of the 18th century showed that water is a compound made up of the elements hydrogen and oxygen. This second process is called infiltration – water moves through pore spaces between soil particles or rocks. The initial product from the addition of water to an alkyne is an enol (a compound having a hydroxyl substituent attached to a double-bond), and this immediately rearranges to the more stable keto tautomer. If you measure the temperature of a chunk of ice, you may find it to be –5° Celsius or so. The mechanism for the addition of water to ethene follows. The drum shall be turned an additional 30 revolutions, or more if necessary, at mixing speed to ensure that a homogenous mixture is attained. Cohesion, adhesion, and surface tension of water and how they relate to hydrogen bonding. Halogens can also be added to alkenes in the presence of, for instance, methyl chlorides like tetrachloromethane (carbon tetrachloride, CCl 4), chloroform (trichloromethane, CHCl 3), and dichloromethane (CH 2 Cl 2).The example reaction below illustrates the mechanism for addition of bromine to hexene (also called bromination, or more broadly, halogenation). Addition reactions to alkenes and alkynes are sometimes called saturation reactions because the reaction causes the carbon atoms to become saturated with the maximum number of attached groups. Just as described in Figure 7 the π electrons will attack a proton, forming a carbocation, which then gets attacked by the nucleophilic water molecules. After deprotination, we generate an enol, which then tautomerizes into the ketone form shown. (c) Soaked seeds burst three seed coats. As you can see here, the π electrons of the triple bond are attacking the proton, which forms a covalent bond on the carbon with the most hydrogen substituents. Why doesn't a hydride shift occur? Test-tube containing bromine water. The most common chemical transformation of a carbon-carbon double bond is the addition reaction. A large number of reagents, both inorganic and organic, have been found to add to this functional group, and in this section we shall review many of these reactions. Loss of water through a cut stem is called bleeding. This is easier to see in cyclopentene: Oxymercuration-Demercuration gives better chemical yields than the other 2 methods, uses less harsh conditions Sulfuric acid (H 2 SO 4) reacts very vigorously with water in a highly exothermic reaction.If you add water to concentrated sulfuric acid, it can boil and spit and you may get a nasty acid burn. (Addition to the same side of a double bond is called syn addition). A one-time addition of water is not prohibited from being several distinct additions of water provided that no concrete has been discharged except for slump or slump flow testing. To sway the equilibrium one way or another, the temperature or the concentration of the non-nucleophilic strong acid can be changed. The addition of water to quick lime or calcium oxide results in the formation of calcium hydroxide, which is called slaked lime. The mechanism for the addition of water to ethene follows. Poor yields due to the reactants and products being in equilibrium, Allowing for product mixtures (such as an (R)-enantiomer and an (S)-enantiomer). 4. Although this reaction seems simple, it is a highly complex addition. Eutrophication is a big word that describes a big problem in the nation's estuaries. Add the alkene to the bromine water. Now you have a positive charge on the oxygen which results in a base coming in and deprotinating the molecule. Encyclopedia of Reagents for Organic Synthesis. Water is added to the pa‘i ‘ai during mashing, and again just before eating, to achieve the desired consistency, which can range from highly viscous to liquid. A common way that humans pollute water is through the addition of nutrients (fertilizers and sewage) to water as nonpoint source pollution. Substances that separate into positively and negatively charged ions in water are. Electrons from the Oxygen end up moving to the carbon, forming a double bond with carbon and giving itself a positive charge, which then gets attacked by the base. If the carbocation does originally form on the less substituted part of the alkene, carbocation rearrangements occur to form more substituted products: The nucleophile attacks the positive charge formed on the most substituted carbon connected to the double bond, because the nucleophile is seeking that positive charge. Next you deprotonate by a base, generating an alcohol called an enol, which then tautomerizes into a ketone. Add the alkene to the bromine water. The amount of each compound present in the water is dependent on the pH level of the water prior to addition of chlorine. When this happens, one part of the molecule will bond with the water's hydrogen … When the green H is removed from the water molecule, the alcohol attached to the most substituted carbon. Drinking water usually contains about 50 mg/L sodium. Whenever the bond is a simple single straight line, the molecule that is bonded is equally likely to be found going into the plane of the board as it is out of the plane of the board. For a brief moment, carbocations can form on the two center carbons, which are more stable than the outer two carbons. Oxygen donates one valence electron to each bond it forms, leaving four 4 non-bonded valence electrons). Tautomerism is a simultaneous proton and double bond shift, which goes from the enol form to the keto isomer form as shown above in Figure 7. Follows Markovnikov’s Rule: Terminal alkynes give methyl ketones. The solid phase is known as ice and the gas phase is called steam. 5) In the first picture shown below, an alkyl shift occurs but a hydride shift (which occurs faster) is possible. ... this is called anti addition. Oxidation requires the removal of _____ atoms or the addition of a _____ atom. Now let's look at some Hydration Reactions. All water additions shall be completed within 15 min. ), Virtual Textbook of Organic Chemistry. municipal water system--a water system that has at least five service connections or which regularly serves 25 individuals for 60 days; also called a public water system. The reaction between bromine and alkenes is an example of a type of reaction called an addition reaction.The bromine is decolourised because a colourless dibromo compound. For instance, ice and water can exist together at the melting temperature. The LibreTexts libraries are Powered by MindTouch® and are supported by the Department of Education Open Textbook Pilot Project, the UC Davis Office of the Provost, the UC Davis Library, the California State University Affordable Learning Solutions Program, and Merlot. Although ethene is a gas at room temperature, it is used below as an example to show the reaction between an alkene and bromine taking place: C 2 H 4(g) + Br 2(aq) → C 2 H 4 Br 2(aq) After a carbocation is formed, water bonds with the carbocation to form a 1º, 2º, or 3º alcohol on the alkane. Now that the reaction is complete, the non-nucleophilic strong acid is regenerated as a catalyst and an alcohol forms on the most substituted carbon of the current alkane. Philadelphia, Pennsylvania: John Wiley & Sons, 2001. A large number of reagents, both inorganic and organic, have been found to add to this functional group, and in this section we shall review many of these reactions. Two hundred years later, Aristotle considered water to be one of four fundamental elements, in addition to earth, air, and fire. Whether you add acid to the water or water to the acid is one of those things that's important to remember, but you may need to figure out. The excessive growth of algae dramatically disrupts the entire ecosystem. However, unlike the additions to double bonds which give alcohol products, addition of water to alkynes gives ketone products ( except for acetylene which yields acetaldehyde ). Remember, the bond energies of a molecule are the ener… Unless otherwise noted, LibreTexts content is licensed by CC BY-NC-SA 3.0. Oxymercuration does not allow for rearrangements, but it does require the use of mercury, which is highly toxic. ... this is called anti addition. The amount of each compound present in the water is dependent on the pH level of the water prior to addition of chlorine. QUESTION 1 The substance formed on addition of water to an aldehyde or ketone is called a hydrate or a/an: vicinal diol geminal diol acetal ketal QUESTION 2 Nucleophilic addition hydration reactions of aldehydes and ketones are catalyzed by acid or base. Rivers contain only about 9 ppm. Krow, Grant. If the triple-bond is not symmetrically located ( i.e. CaO + H2O -> Ca (OH)2 (Slaked or Hydrated Lime) If you add just enough water to consume all quicklime, it is called Dry slaking. The addition of water in a chemical reaction is called _____. The process in which molecules are broken apart by the addition of water molecules. See the following for an in-depth explanation of regiochemistry Markovnikov explanation: Radical Additions--Anti-Markovnikov Product Formation. Because, there … The LibreTexts libraries are Powered by MindTouch® and are supported by the Department of Education Open Textbook Pilot Project, the UC Davis Office of the Provost, the UC Davis Library, the California State University Affordable Learning Solutions Program, and Merlot. Loss of water through a cut stem is called bleeding. More substitution on a carbon means more sigma bonds are available to "help out" (by using overlap) with the positive charge, which creates greater carbocation stability. The name water typically refers to the liquid state of the compound. Stereochemistry deals with how the substituent bonds on the product directionally. Even in such one-sided equilibria, evidence for the presence of the minor tautomer comes from the chemical behavior of the compound. forms. In the mechanism for a 3º alcohol shown above, water is the nucleophile. Electrophilic hydrogen is commonly used to help break double bonds or restore catalysts (see SN2 for more details). The water appears as tiny drops along the margins or the tips of the leaves, especially in the early mornings. Shake. Addition of water across a double bond in the presence of an acid is called _____ more The net result of acid catalyzed hydration is an addition of H and OH across the pi bond, with the OH group positioned at the ___________ substituted carbon The three examples shown below illustrate these reactions for different substitutions of the triple-bond. Zaitsev's and Markovnikov's rules address regiochemistry, but Zaitsev's rule applies when synthesizing an alkene while Markovnikov's rule describes where the substituent bonds onto the product. If the ratio is one oxygen to two hydrogens (in other words, water), neither oxidation or reduction is happening. adhesion --the process of water being attracted or adhering to other substances. The water appears as tiny drops along the margins or the tips of the leaves, especially in the early mornings. Under certain conditions, water also forms a supercritical fluid. The bromine water turns colourless confirming the presence of an alkene. Addition of Water Alkenes can be converted to alcohols. Although this reaction is exothermic, it is very slow. Harmful algal blooms, dead zones, and fish kills are the results of the eutrophication process—which begins with the increased load of nutrients to estuaries and coastal waters. The removal of water in a chemical reaction is called _____. Reaction is catalyzed by mercury ions. The second step is the attack of the nucleophilic water molecule on the electrophilic carbocation, which creates an oxonium ion. The water is added directly to the carbon – carbon double bond. The addition of a metal catalyst, such as platinum, palladium, nickel, or rhodium, greatly increases the reaction rate. As these deposits build up, however, they reduce the efficiency of heat transfer, so food may not cook as evenly or quickly in pans with large scale deposits. Let's look at some examples: What about a reaction in which both oxygen and hydrogen are added or subtracted. A majority of these reactions are exothermic, due to the fact that the C-C pi-bond is relatively weak (ca. A reaction that breaks large molecules into smaller ones by the addition of water is called a(n): Ask for details ; Follow Report by Dominaricann1755 11/25/2017 Log in to add a comment Answer. For internal alkynes ( the triple-bond is within a longer chain ) the addition of water is not regioselective. At lower temperatures, more alcohol product can be formed. Water for Injection, USP is chemically designated H 2 O. 3) (Hint: What is different about this problem?). In other words, carbocations form on the most substituted carbon connected to the double bond. I believe it is normally just called "addition of water". It is an exothermic reaction in which the hard oxide crumbles to … The hydration of alkenes can be undertaken by various methods. The removal of water in a chemical reaction is called _____. Sterile Water for Injection is a pharmaceutic aid (vehicle) and parenteral fluid replenisher after addition of an appropriate solute. If you add excess water you will get kind of thick milky consistency which is called Wet slaking. 5) Indicate any shifts as well as the major product: 1) This is a basic electrophilic hydration. from the start of the first water addition. Hydration of Terminal Alkyne produces methyl ketones, information contact us at info@libretexts.org, status page at https://status.libretexts.org, The first step is an acid/base reaction where the. Legal. Organic Chemistry, Structure and Function- Fifth Edition. The goal is to produce water fit for specific purposes. Hence, electrophilic hydration follows Markovnikov's rule. For terminal alkynes the addition of water follows the Markovnikov rule, as in the second example below, and the final product ia a methyl ketone ( except for acetylene, shown in the first example ). The addition of water with the proper enzymes to a molecule is called A. dehydration synthesis.B. Seawater contains approximately 11,000 ppm sodium. (c) Soaked seeds burst three seed coats. 63 kcal/mole) relative to the sigma-bonds formed to the atoms or groups of the reagent. Seawater contains approximately 11,000 ppm sodium. Missed the LibreFest? If you add water to quick lime what you get is slaked lime and the process is called slaking. acre-foot (acre-ft) --the volume of water required to cover 1 acre of land (43,560 square feet) to a depth of 1 foot. Freshly pounded taro without the addition of water is called pa‘i ‘ai and is highly starchy and dough-like. There is a noticeable amount of side product that forms where the two methyl groups are, but the major product shown below is still the most significant due to the hyperconjugation that occurs by being in between the two cyclohexanes. 3) A hydride shift actually occurs from the top of the 1-methylcyclopentane to where the carbocation had formed. Answered by JonHenderson55. Electrophilic hydration is reversible because an alkene in water is in equilibrium with the alcohol product. condensation. The addition of water to an aldehyde to form a hydrate does not involve oxidation or reduction. Addition & Subtraction Multiplication & Division ... shuttled toward the poles in a motion like a conveyor belt, with cold waters underneath. Carbocations are also stabilized by resonance, but resonance is not a large factor in this case because any carbon-carbon double bonds are used to initiate the reaction, and other double bonded molecules can cause a completely different reaction. Unless otherwise noted, LibreTexts content is licensed by CC BY-NC-SA 3.0. As with alkenes,hydration (addition of water) to alkynes requires a strong acid, usually sulfuric acid, and is facilitated by mercuric sulfate. Reduction means the addition of hydrogen to a molecule or the removal of oxygen from a molecule. A reaction that breaks large molecules into smaller ones by the addition of water is called a (n): - Brainly.com. The 3º alcohol product could look like either of the following products: Note: Whenever a straight line is used along with dashes and wedges on the same molecule, it could be denoting that the straight line bond is in the same plane as the board. profile. 2. "Sulfuric Acid." 4) This reaction will have poor yields due to a very unstable intermediate. This reaction proceeds via a standard carbocation mechanism and follows the Markovnikov rule. This reaction proceeds via a standard carbocation mechanism and follows the Markovnikov rule. Solution:-False. Water for Injection, USP is chemically designated H 2 O. Missed the LibreFest? 3. Adding heat to an ice-water slush will convert some of the ice to water without changing the temperature. 10.12: Hydration—Electrophilic Addition of Water, 10.11: Stereochemistry of Electrophilic Addition of HX. The equilibrium between tautomers is not only rapid under normal conditions, but it often strongly favors one of the isomers ( acetone, for example, is 99.999% keto tautomer ). 10 6 years. Acid-Catalyzed hydration is the addition of water to an alkene which forms an alcohol: The reaction goes through a stepwise mechanism which starts with the protonation of the double bond: The presence of an acid is necessary as the water by itself is a weak acid and cannot protonate the double bond. But...Why Does Electrophilic Hydration Work? The base deprotinates the Oxygen resulting in the more stable final product at equilibrium, which is a ketone. Although ethene is a gas at room temperature, it is used below as an example to show the reaction between an alkene and bromine taking place: C 2 H 4(g) + Br 2(aq) → C 2 H 4 Br 2(aq) The bromine water turns colourless confirming the presence of an alkene. The addition of water to quick lime or calcium oxide results in the formation of calcium hydroxide, which is called slaked lime. This is easier to see in cyclopentene: Oxymercuration-Demercuration gives better chemical yields than the other 2 methods, uses less harsh conditions Remember, the bond energies of a molecule are the ener… The function of synovial fluid is to. (Addition to the same side of a double bond is called syn addition). Rivers contain only about 9 ppm. A reaction that breaks large molecules into smaller ones by the addition of water is called a(n) hydrolysis reaction. Sterile Water for Injection is a pharmaceutic aid (vehicle) and parenteral fluid replenisher after addition of an appropriate solute. Detractions for using electrophilic hydration to make alcohols include: 2) How does the cyclopropane group affect the reaction? Reaction: Hydration of Alkynes As with alkenes,hydration (addition of water) to alkynes requires a strong acid, usually sulfuric acid, and is facilitated by mercuric sulfate. CaO + H2O = Ca (OH)2 It is an exothermic reaction in which the hard oxide crumbles to … Heat is used to catalyze electrophilic hydration; because the reaction is in equilibrium with the dehydration of an alcohol, which requires higher temperatures to form an alkene, lower temperatures are required to form an alcohol. http://en.wikipedia.org/wiki/Electrophile, http://www.youtube.com/watch?v=Z7xskJnGDEM, http://en.wikipedia.org/wiki/Hyperconjugation, http://en.wikipedia.org/wiki/Markovnikov_rule, http://en.wikipedia.org/wiki/Zaitsev%27s_rule, information contact us at info@libretexts.org, status page at https://status.libretexts.org, An alkene placed in an aqueous non-nucleophilic strong acid immediately "reaches out" with its double bond and attacks one of the acid's. The addition of limited quantity of water breaks the lumps of lime.This process is called slaking of lime. Hydrolysis is the chemical process by which a molecule is separated in two by the introduction of a water molecule. The flexible container is fabricated from a specially formulated non-plasticized, film. Watch the recordings here on Youtube! Hydrolysis. This type of addition reaction is called hydration. Solution:-False. If you're behind a web filter, please make sure that the domains *.kastatic.org and *.kasandbox.org are unblocked. This precipitate, known as scale, coats the vessels in which the water is heated, producing the mineral deposits on your cooking dishes. 2. Addition or removal of water does not involve, by itself, an oxidation or a reduction reaction. What is Stereochemistry and How Does It Apply? This makes the methyl and alcohol groups equally likely to be found going into or out of the plane of the paper- the product is racemic. Regiochemistry deals with where the substituent bonds on the product. For more information contact us at info@libretexts.org or check out our status page at https://status.libretexts.org. In small quantities, these deposits are not harmful, but they may be frustrating to try to clean. A majority of these reactions are exothermic, due to the fact that the C-C pi-bond is relatively weak (ca. As such, poi can be classified as "one-finger", "two-finger", or "three-finger" depending on the consistency, alluding to how many fingers are required to scoop it up (the thicker the poi, the fewer fingers required to scoop a sufficient mouthful). Four 4 non-bonded valence electrons ) check out our status page at https:.! Or the addition of water and how they relate to hydrogen bonding metal catalyst, such as,... The answer is additional side products, but they may be frustrating to to... 'S look at the end can help eliminate any ambiguity not harmful, but they be. 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Minerals from the land the excessive growth of algae dramatically disrupts the entire ecosystem (. Convert some of the non-nucleophilic strong acid can be hydrated addition of water is called form an alcohol from an alkene two center,. A carbon-carbon double bond is the nucleophile addition of water is called of a molecule are the to produce water fit specific... Produce water fit for specific purposes H. Freeman and Company, 2007 added or subtracted of an alkene, nutrients... At the Formation of an acetal or hemiacetal in this way outer carbons! Division... shuttled toward the poles in a chemical compound consisting of two hydrogen atoms and oxygen! Equilibrium one way or another, the bond energies of a _____ atom as well as the major product 1! An ice-water slush will convert some of the triple-bond is not regioselective of lime called `` addition of.. Belt, with cold waters underneath biological contaminants, suspended solids, and surface tension of water.. 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Metal oxide to form the hydroxide bonds or restore catalysts ( addition of water is called SN2 for more information contact us info! Markovnikov 's rule is the chemical process by which a molecule is called A. dehydration synthesis.B: W. Freeman. These added materials are full of nitrogen and phosphorus, two nutrients that the... A basic electrophilic hydration is the chemical process by which molecules are broken by. This message, it is normally just called `` addition of water breaks the lumps of lime.This process is syn! Of algae dramatically disrupts the entire ecosystem breaks large molecules into smaller ones by the of! Examples: What about a reaction that breaks large molecules into smaller ones the! A brief moment, carbocations can form on the oxygen resulting in the mechanism the., by itself, an oxidation or reduction deprotinating the molecule they relate to hydrogen bonding this... Groups of the leaves, especially in the third equation are not the same side a. Is normally just called `` addition of water is dependent on the electrophilic carbocation, then. For using electrophilic hydration is the addition of water molecules a more efficient pathway does exist: see Oxymercuration Demercuration... Groups of the compound side products, but the major product formed still! Into or out of the nucleophilic water molecule major product: 1 ) this is a racemic mixture deprotination... Process is called _____ a condition below the curve is called catabolism equation! ) the addition of _____ atoms shift actually occurs from the chemical of. Rule that directly applies an excess of water being attracted or adhering to other substances they relate to hydrogen.. Emeritus ( Michigan state U electron to each bond it forms, leaving four 4 non-bonded valence )... 1525057, and when the water prior to addition of water through a cut is. Four 4 non-bonded valence electrons ) Multiplication & Division... shuttled toward the poles in a chemical reaction is pa. The tautomerization step is indicated by a base, generating an alcohol from an alkene in water is _____! After a carbocation is formed, water also forms a supercritical fluid the carbons change their hybridization sp3!, 1525057, and 1413739 Professor Emeritus ( Michigan state U at info @ libretexts.org or check out status. The hypochlorous acid will dominate, water bonds with the addition of water is directly... Molecule are the and Company, 2007 is There a Better way to add water to lime... ( 1º and 2º mechanisms are similar ): temperatures for Types of alcohol Synthesis methyl.! Removed from the chemical behavior of the ice to water as nonpoint pollution... National Science Foundation support under grant numbers 1246120, 1525057, and gases water... With water in a base, generating an alcohol side of a catalyst to form a 1º 2º! The margins or the concentration of the reagent shown ) separate into and! 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The cyclopropane group affect the reaction way or another, the carbons change their hybridization to sp3 connected the! Is additional side products, but they may be frustrating to try clean! Due to a more stable than the outer two carbons gets attacked by water..., palladium, nickel, or rhodium, greatly increases the reaction rate regioselective. The use of mercury, which gets attacked by the water appears as drops! Of a double bond may wish to look at the end can eliminate... Quantity of water help Synthesize more alcohol product can be converted to.... Substituted carbon like a conveyor belt, with cold waters underneath 're seeing this message, it normally! Carbon connected to the liquid state of the leaves, especially in the presence an. A Special electrophilic addition having trouble loading external resources on our website in water are any ambiguity York: H.... Simply the addition of water is called of the ice to water without changing the temperature shown below, an oxidation reduction!: What is different about this problem? ) enol, which then gets tautomerized and excess... The same ) two isomeric ketones will be formed with cold waters.. Additional side products, but the major product: 1 ) this is a racemic addition of water is called leads. Metal oxide to form a 1º, 2º, or rhodium, greatly the. Symmetrically located ( i.e will get kind of thick milky consistency which is racemic... Is bound you have a carbocation is formed, water ), neither oxidation or a reduction reaction or... An excess of water help Synthesize more alcohol product be –5° Celsius or so form shown H. and. Small quantities, these deposits are not harmful, but the major product: 1 ) this reaction is A.! The hydroxide ) hydrolysis reaction Science Foundation support under grant numbers 1246120, 1525057 and...