As shown below, this addition consists of adding a nucleophile and a hydrogen across the carbonoxygen double bond. Reaction score. 20. Answer (1 of 20): NaOH(s) + H2O(l) => Na+ + OH- + H20 + HEAT Remember that proton transfers from oxygen to oxygen are virtually always extremely fast. Reactions of aldehydes and ketones with amines and amine derivatives a. #"CH"_3"CO" stackrelcolor (blue)("-")("C")"H"_2 + "CH"_3"COCH"_3 "CH"_3"COCH"_2"C(CH"_3")"_2"-"stackrelcolor (blue)("-")("O")#. The reaction takes place at 450 C. . Retro Aldol Reaction-reverse three steps of aldol addition . Some Maillard reactions occur at room . Rizzo 2. This reaction turns a methyl ketone into haloform and an acid (or its conjugate base). This problem has been solved! The products of aldol reactions often undergo a subsequent elimination of water, made up of an alpha-hydrogen and the beta-hydroxyl group. Reagents Ketone Product 1. Step 1: List the known quantities and plan the problem . Due to the unshared electron pair, amines can act as both bases and nucleophiles. 6.22 (a) Reaction (2) because bromide ion is a better leaving group than chloride ion. Due to the carbanion like nature of enolates they can add to carbonyls in a similar manner as Grignard reagents. Industrial Area: Lifting crane and old wagon parts, What Time Does Green Dot Post Tax Refunds, how to make hot tamales with aluminum foil, medial meniscal extrusion: detection, evaluation and clinical implications, mobile homes for rent in osceola county, fl, the reserve club aiken, sc membership cost. Sodium hypochlorite is an inexpensive, strong oxidizing agent, that is used as disinfectant and bleaching agent. When reacted with acids, amines donate electrons to form ammonium salts. 2. The reaction isn't normally done using hydrogen cyanide itself, because this is an extremely poisonous gas. Big 12 Football Referees List, Formation of a yellow precipitate of solid iodoform signals a positive test and indicates that the sample is a . The mechanism for cyclization via an aldol proceeds through an enolate attack on the aldehyde carbonyl. Reaction with 2o amine gives 3o amide (rxn not shown) Reaction with 3o amine does not give amide, only neutralization products. They undergo the electrophilic additions like halogenation and hydrohalogenation. MnO2, heat: No Products Predicted. It also reacts with weak-acid gases, such as hydrogen sulfide, sulfur dioxide, and carbon dioxide.Caustic soda reacts with amphoteric metals (Al, Zn, Sn) and their oxides to form complex anions such as AlO2(-), ZnO2(-2), SNO2(-2), and H2 (or H2O with oxides). The enolate anion attacks the carbonyl carbon in another acetone molecule. with NaBH4 or LiAlH4. The loss of a hydrogen ion to the oxygen anion stabilizes the oxonium ion formed in Step 1. (i) Propanal (CH 3 CH 2 CHO) can be distinguished from propanone (CH 3 COCH 3) by iodoform test.. The generation of sodium hypoiodate in solution from the reaction of iodine with sodium hydroxide leads to the formation of iodoform and sodium benzoate, as shown here. Removing #book# (Cleavage of alkenes only to give aldehydes and/or ketones) (Ch. This is destroyer question 7 in orgo. 2) From the aldol product break the C-C bond between the alpha carbon and the carbon attached to the OH. Note! 2. Reaction with 1o amine gives a 2o amide. Take ester in methanol and add methanolic HCL then heat it to 60-65C,finally ester converted to Acid Cite It depend upon the nature of ester you want to hydrolyze it is possible to hydrolyze in. Base-driven alpha halogenation yields an unusual result for methyl ketones. Ask a Aldehydes & Ketones question , get an answer. Base-catalyzed elimination occurs with heating. learn. Such a-hydrogen atom . Dr. Dietmar Kennepohl FCIC (Professor of Chemistry, Athabasca University), Prof. Steven Farmer (Sonoma State University), William Reusch, Professor Emeritus (Michigan State U. The answer is D) 3-hydroxy-2-methlypentanal. Main Menu. NaOH, H2O, heat (Ch.20) Wolff-Kishner Reduction: Reduces a hydrazone to an alkane (Ch.20) 1) LAH 2) H20. If all the reactions occurred at the same rate, equal quantities of the four products would be obtained. indicating stereochemistry where appropriate. Compounds (C) and (D) are not positive to Iodoform test. Note: One of the reactions is a poorly designed aldol condensation producing four different products. Without heat and only NaOH, H2O- dehydration can occur if it leads to a highly conjugate product (to an aromatic ring or another pi system) DEHYDRATION of ALDOLS -Acid Catalyzed two aldehydes, two ketones or one aldehyde, one ketone , - unsaturated carbonyl H 2 SO 4, H 2 O - Acid catalyst in aldol formation will always lead to the . Dissolution of solid sodium hydroxide in water is a highly exothermic reaction where a large amount of heat is liberated The following reaction is under consideration NaOH (s) + H2O (l) => Na+ + OH- + H20 + HEAT In ethanal, there is one carbon and three hydrogens, while in acetone there are two carbons and six hydrogens. The reaction is as follows: 2Mg + 2NaOH -> 2MgO + 2Na + H2 This reaction works because the magnesium (Mg) is able to rip the oxygen molecule right out of the sodium hydroxide (NaOH). The resulting compounds, hydroxy aldehydes, are referred to as aldol compounds because they possess both an aldehyde and alcohol functional group. The reaction between benzaldehyde and acetophenone undergo cross aldol condensation in presence of dil. Aldehydes and ketones react with primary amines to form a class of compounds called imines. Amines characteristically form salts with acids; a hydrogen ion, H+, adds to the nitrogen. Draw reaction with a primary amine forms an imine. Sodium cannot bind to hydrogen alone, so with the oxygen gone, both remaining elements are free. Derivatives of imines that form stable compounds with aldehydes and ketones include phenylhydrazine, 2,4dinitrophenylhydrazine, hydroxylamine, and semicarbazide. Aldol reactions are excellent methods for the synthesis of many enones or beta hydroxy carbonyls. What is N-(2,2,2-Trichloroethyl)carbonyl] Bisnor-(cis)-tilidine's functional group? NaOH. The hydroxy group is protonated to yield an oxonium ion, which easily liberates a water molecule. Notes: The choice of H 2 O / H 2 SO 4 as acid isn't crucial - this is just an example. NaBH3CN CH3OH: Note: Reductive amination couples amines and carbonyls (aldehydes and ketones). The aldol reactions for acetaldehyde and acetone are shown as examples. The reaction of aldehydes or ketones with phosphorus ylides produces alkenes of unambiguous doublebond locations. 3. Ketones usually do not form stable hydrates. An unshared pair of electrons on the nitrogen migrate toward the positive oxygen, causing the loss of a water molecule. 1. The product in such cases is always a dimer of the reactant carbonyl compound. dilute sulphuric acid (H 2 SO 4) or hydrochloric acid (HCl) or a strong alkali such as sodium hydroxide (NaOH), they are hydrolyzed slowly to carboxylic acid and alcoholic groups.. Acid-catalyzed hydrolysis of esters Proton abstraction to form a resonance-stabilized enolate ion. Step 2: Nucleophilic attack by the enolate. The alkoxide ion abstracts a proton from water in an acidbase reaction. Mechanism: NH 2 NH 2 In The Wolff-Kishner Reaction How it works. It will be greater than 7. -heat allows for decarboxylation forms one subbstitued carboxylic acid and one carbon dioxide . Various aryl alkyl ketones could be converted into their corresponding aryl carboxylic acids in very good yields. Aldol condensations between different carbonyl reactants are called crossed or mixed reactions, and under certain conditions such crossed aldol condensations can be effective. MnO2, heat: No Products Predicted. Maillard Reaction Lab-1 Introduction: Maillard is a chemical reaction between amino acids and reducing sugars that gives brown color of foods and their desirable flavor. No special permission is required to reuse all or part of the article published by MDPI, including figures and tables. This accomplished by mentally breaking apart the target molecule and then considering what the starting materials might be. The reaction is to place the ketone in a MeOH solution and add slowly to a stirred suspension of MeOH and NaBH4, continue stirring so that all of the newly formed alcohol Borate adduct is formed and no starting ketone can be detected by TLC, then release the alcohol by shifting the MeOH to have small amount of protonation so that the remaining . NaBH 4 is a source of hydride (H-) and the reaction begins with the addition of hydride to the carbonyl to the aldehyde (Step 1, arrows A and B). It is unstable as a solid, but solutions of up to 40% are commercially available that contain NaOH and NaCl as byproducts of the preparation: 2 NaOH + Cl 2 NaCl + NaOCl + H 2 O. Hypochlorite solutions liberate toxic gases such as . Menu. With acid catalysts, however, small amounts of aldol product can be formed. The product of this \ (\beta\)-elimination reaction is an ,-unsaturated aldehyde or ketone. Hydration of Aldehydes and Ketones + H2O a gem-diol (hydrate) acid- or base-catalyzed Steric hindrance, electron donating groups destabilize hydrate. 01 1401 - 23:19 . Also, ninhydrin is commonly used by forensic investigators to resolve finger prints. Caustic soda reacts with all the mineral acids to form the corresponding salts. Q,) NaOH, H2O, heat. c) Provide the type equations used in the test. A methyl ketone will react until three halogens have been substituted on the -carbon! NaOH: Warning: Haloform reaction. NaOH, H2O, heat Code oc Compounds Check which of the following statements are TRUE. However, shouldn't the -OH on one carbon and -H on the adjacent carbon leave in the form of water thus making a double which owuld mean the answer choice SHOULD be E) 2-methyl-2-pentEnal? Two examples of this are chloral, and 1,2,3-indantrione. tutor. Accessibility StatementFor more information contact us atinfo@libretexts.orgor check out our status page at https://status.libretexts.org. Please explain your answer. Step 1: First, an acid-base reaction. H2O, (H+) Note: Higher order amides can be reduced to form higher order amines. Imines of aldehydes are relatively stable while those of ketones are unstable. Study Resources. Proton abstraction to form a resonance-stabilized enolate ion. The reaction is a form of nonenzymatic browning which occurs in a wide temperature range. A reaction with water protonates the alkoxide ion. Because of this most mixed aldol reactions are usually not performed unless one reactant has no alpha hydrogens. Figure 6. The fundamental transformation in this reaction is a dimerization of an aldehyde (or ketone) to a beta-hydroxy aldehyde (or ketone) by alpha CH addition of one reactant molecule to the carbonyl group of a second reactant molecule. Steps to 'reverse' the aldol reaction (from the final aldol product towards identifying the starting compounds). The mechanism for imine formation proceeds through the following steps: 1. Notice in the previous reaction that the ketone carbonyl group has been reduced to an alcohol by reaction with LiAlH 4. LDA, -78 C 2. Are you sure you want to remove #bookConfirmation# However, ketones can be oxidized to various types of compounds only by using extremely strong oxidizing agents. In the presence of a base, ketones with hydrogens react to form haloketones. AFM images show that the hydrophilic side chain and hydrophobic main chain form a distinct microphase separation structure. The carbanion is resonancestabilized. When performing both reactions together always consider the aldol product first then convert to the enone. Proton abstraction to form a resonance-stabilized enolate ion. 7 mins. MECHANISM OF THE ALDOL REACTION. To be useful, a crossaldol must be run between an aldehyde possessing an hydrogen and a second aldehyde that does not have hydrogens. For this reaction to occur at least one of the reactants must have alpha hydrogens. This is often referred to as " deprotection " of aldehydes or ketones. The reaction involves several steps. Otherwise only neutralization occurs . A useful carbon-carbon bond-forming reaction known as the Aldol Reaction is yet another example of electrophilic substitution at the alpha carbon in enolate anions. Unfortunately, your shopping bag is empty. Fluorine is more electronegative than bromine and would remove more electron density from the carbonyl carbon. As a base, it's often used in situations where a strong, small base is required. When sodium borohydride is in a strongly basic solution (at or above pH 10), it is stabilized against reaction with water, although addition of water may still be exothermic due to heat of solvation. NaOH, H2O BrBr Br HBr NaOH, H2O C C O Br Br Br2 C CBr O BrBr 243 Haloform reaction: Iodoform reaction: chemical tests for a methyl ketone C C X O X X CH3 C ONa H,2 X2 OH C OH C O + CX 3 O C O + HCX Haloform RCH3 C ONaH,2O I2 RO + HCI3 . We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. Distinguishing Tests between Aldehydes and Ketones: (c) Schiff's Test: My answer turns out to be an intermediate. The protected aldehyde group has not been reduced. It is unstable as a solid, but solutions of up to 40% are commercially available that contain NaOH and NaCl as byproducts of the preparation: 2 NaOH + Cl 2 NaCl + NaOCl + H 2 O. Hypochlorite solutions liberate toxic gases such as . [11] Methoxybenzene is an activator AND a meta-director One method of shifting the equilibrium in the direction of the ester, in the Fischer esterification reaction This problem has been solved! This decent leaving group allows the carbonyl to undergo a nucleophilic acyl substitution reaction with the NaOH already present in the reaction. The aldol reaction has a three-step mechanism: Step 1: Enolate formation. Stir the mixture at r.t. while adding 500 l of 10% NaOH solution. police academy running cadences. NaOH, H2O 3. Aldehydes can be oxidized to carboxylic acid with both mild and strong oxidizing agents. In most cases, the keto form is more stable. The loss of water from 3 may be stepwise but, to save space, I have presented the loss of water in a single operation. A proton is transferred from the nitrogen to the oxygen anion. K eq for dehydration is generally large and, if reaction conditions bring about dehydration, good yields of product can be obtained It takes special efforts to isolate an Aldolthe product is generally the a,b -unsaturated aldehyde or ketone Note: Formation of crystalline precipitate confirms carbonyl group. Adding hydroxyl ions changes the nucleophile from water (a weak nucleophile) to a hydroxide ion (a strong nucleophile). Now, the efficiency of the addition reactions to an aldehyde or a ketone is determined by how electrophilic the C=O carbon atom is. naoh h2o heat reaction with ketoneexamples of misfeasance in healthcare. Carbonyl Compounds: Reaction of octane-2,7-dione with NaOH Part A Two distinct reactions occur sequentially when the following ketone is treated with a strong base. Aldehydes and ketones undergo a variety of reactions that lead to many different products. The mechanism for the addition of hydrogen cyanide is a straightforward nucleophilic addition across the carbonyl carbony oxygen bond. 23.2 Condensations of Aldehydes and Ketones: The Aldol Reaction The base-catalyzed self-condesnation reaction of acetaldehyde gives 3-hydroxybutanal (aldol) General mechanism of the aldol reaction (Fig. Hydrazine In The Second Step Of The Gabriel Synthesis Hydrazine is also used in the second step of the Gabriel synthesis, for liberating the new amine from the phthalyl group. In general, the reactivity of the carbonyl compound (or any compound for that matter) depends on its stability. It has been demonstrated that water, in the presence of an acid or a base, adds rapidly to the carbonyl function of aldehydes and ketones establishing a reversible equilibrium with a hydrate (geminal-diol or gem-diol). C O R C ethr O H3O + R C O +R-Li Li RCCH + NaH 2 RCCNa++NH 3 pK a~ 36 RC CH+ H 3C(H 2) 2 C-Li R Li++ HC(2) pK a > 60 RC CH+H 3H 2C-MgBr RCMgBr++ HCCH pK a > 60 pK a~ 26 311 Recall from Chapter 9.6 Acetylide anions react with ketones and . This occurs because the addition of acid causes a protonation of the oxygen of the carbonyl group, leading to the formation of a full positive charge on the carbonyl carbon, making the carbon a good nucleus. Solution for Draw the alkyl chloride for reaction 2. Although weakly acidic (K a 10 19 to 10 20), hydrogens can react with strong bases to form anions. Note: This reagent only works on benzylic alcohols, not 'regular' alkyl alcohols: Zn(Hg) HCl, heat: Note: Clemmenen reduction converts aldehydes and ketones into alkanes under . The main reactions of the carbonyl group are nucleophilic additions to the carbonoxygen double bond. write. The oxonium ion loses a proton to an alcohol molecule, liberating the acetal. Reactions of aldehydes with alcohols produce either hemiacetals (a functional group consisting of one OH group and one OR group bonded to the same carbon) or acetals (a functional group consisting of two OR groups bonded to the same carbon), depending upon conditions. Compound (D) reacts with N H 2 O H to give (F) and compound (E) reacts with NaOH to give an . 3. NaOH, H2O, heat O Et 4. The aldol condensation proceeds via a carbanion intermediate. of acetone. Figure 6. 2. The reaction is carried out in solution in an alcohol like methanol, ethanol or propan-2-ol. Acid-Catalysed Bromination of Ketones CONTROLS 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 most common reactions are nucleophilic addition reactions, which lead to the formation of alcohols, alkenes, diols, cyanohydrins (RCH (OH)C&tbond;N), and imines R 2 C&dbond;NR), to mention a few representative examples. Typical oxidizing agents for aldehydes include either potassium permanganate (KMnO 4) or potassium dichromate (K 2Cr 2O 7) in acid solution and Tollens reagent. Isolation of gem-diols is difficult because the reaction is reversibly. Legal. #"CH"_3"COCH"_2"C(CH"_3")"_2"-"stackrelcolor (blue)("-")("O") + "H"_2"O" underbrace("CH"_3"COCH"_2"-C"("CH"_3)_2"-OH")_color(red)("4-hydroxy-4-methylpentan-2-one") + "OH"^-#. Hydrolysis of the reduction product recreates the original aldehyde group in the final product. All articles published by MDPI are made immediately available worldwide under an open access license. Bromination of ketones occurs smoothly with bromine in acetic acid. First, the -CH 3 on a methyl ketone is converted to a trihalomethyl group. We've got the study and writing resources you need for your . Step 3: An acid-base reaction. This condensation leads to the formation of hydroxy ketones. A) O O B) OO C) D) O E) O O H3C Ans: B. C8. 2) Of the following pairs of molecules which would you expect to form a larger percentage of gem-diol at equilibrium? The product of this \(\beta\)-elimination reaction is an ,-unsaturated aldehyde or ketone. This dehydration step drives the reaction to completion. (B) undergoes a positive iodoform reaction and reacts with phenylhdrazine. Ketones tend to not form gem-diols because of the stabilizing effect of the electron donating alkyl group. An excess of water is used to complete the reaction as much as possible. 23.2, page 857) H 3CCH O aceta ldehyde 2 NaEt EtOH C CH 2H OH 3-hydroxbutan (!-hydroxy aldehyde) The base-catalyzed aldol reaction (NaOEt, EtOH . arrow_forward. You will mix together iodine, 2-butanone, and a 10% NaOH solution in a test tube. Reactions of carbonyl groups. The compound (C) readily decolourises bromine water. It should be noted that chloral hydrate is a sedative and has been added to alcoholic beverages to make a Knock-out drink also called a Mickey Finn. The base removes a hydrogen ion to form a resonancestabilized molecule. 2 R1 C C R2 H2SO4, HgSO4 H2O R1 C C R2 O H H R1 C C R2 H O H + H2O H2SO4, HgSO4 H C C R H C C R O H H Owing to the formation of mixtures if R1 R2, this reaction is most useful when R1 = R2or when the alkyne has a terminal triple bond. The acidcatalyzed aldol condensation includes two key steps: the conversion of the ketone into its enolic form, and the attack on a protonated carbonyl group by the enol. 1) What happens to the p H of water when LiAlH 4 is is added to it? The reaction heat is utilized for the production of steam of 20 atmospheres. stoc 2022 accepted papers; the forum inglewood dress code; to what extent is an individual shaped by society; astragalus and kidney disease; lake wildwood california rules and regulations; naoh h2o heat reaction with ketone. This is essentially a 2-step reaction with initial condensation of the amine and carbonyl to form an imine, which the reducing agent then converts into a secondary . The alkoxide ion removes a proton from the hydroxide group. with a Pasteur pipette, transferring it to a test tube containing 0.5 ml of water and 0.5 ml of ethyl acetate, shaking the tube and applying a sample from the top layer to a TLC plate. Note: Benzylic oxidation requires the presence of a benzylic hydrogen, so no reaction occurs here: MnO2, heat: No Products Predicted. . gabby hartnett children; honeymoon suites mooresville, nc; just intonation fret calculator 23.8: The Aldol Reaction and Condensation of Ketones and Aldehydes is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by LibreTexts. Gloria Estefan Band Crossword Clue, In aldehydes, the relatively small hydrogen atom is attached to one side of the carbonyl group, while a larger R group is affixed to the other side. The mechanism for imine formation proceeds through the following steps: 1. compounds with the application of heat with acid or base. 5. #"CH"_3"COCH"_2"-C"("CH"_3)_2"-OH" underbrace("CH"_3"COCH=C(CH"_3")"_2)_color(red)("4-methylpent-3-en-2-one") + "H"_2"O"#. Secondary alcohol on oxidation with K2Cr2O7 + H2SO4 forms ketone. 4. . Acetal hydrolysis [H3O+] Explained: Hydrolysis of acetals is a reverse reaction of acetal formation. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. However, in this case the electron donating effects of alkyl group is dominated by the presence of six highly electronegative fluorines. Aug 7, 2008. Cannizzaro reaction Aldol condensation d) Show the sample equations involved in the reactions between: How Much Garlic Powder Equals 3 Cloves, The reaction between the keto form of acetone 1a and its enol 1b forms aldol 2. Example: Products of a Mixed Aldol Reaction. Hydroxide functions as a base and removes the acidic -hydrogen giving the reactive enolate. 3) From Acetic acid - By passing vapours of acetic acid over heated MnO catalyst at 300 0 C, acetone is formed. With the strong mineral acids (e.g., H2SO4, HNO3, and HCl), the reaction is vigorous. 2. 1. First, an acid-base reaction. Example: Mixed Aldol Reaction (One Product). O NaOH OH Br 2 O Br Br BrBr Haloform Reaction! The electron withdrawing ability of a carbonyl group is caused by the group's dipole nature, which results from the differences in electronegativity between carbon and oxygen. Mixing the two reactants with hydrochloric acid produces an acetal. Overall the general reaction involves a dehydration of an aldol product to form an alkene: Example: Aldol Condensation from an Aldol Reaction Product. Due to differences in electronegativities, the carbonyl group is polarized. Hydrolysis of esters is an example of a nucleophilic substitution reaction. This is called the haloform reaction. Likewise, when methyl ketones react with iodine in the presence of a base, complete halogenation occurs. Preparations: Halo Acids, Hydroxy Acids, and , Unsaturated Acids, Electrophilic Aromatic Substitution Reactions, Nucleophilic Substitution Reactions: Mechanisms. Ylides have positive and negative charges on adjacent atoms. The cyanide ion is the only known catalyst for this condensation, because the cyanide ion has unique properties. First, aldehydes are more reactive acceptor electrophiles than ketones, and formaldehyde is more reactive than other aldehydes. The addition of hydrogen cyanide to a carbonyl group of an aldehyde or most ketones produces a cyanohydrin. #"HO"^(-) + underbrace("CH"_3"COCCH"_3)_color(red)("acetone") underbrace([stackrelcolor (blue)("-")("C")"H"_2"COCH"_3 "CH"_2"=C(CH"_3")-"stackrelcolor (blue)("-")("O")])_color(red)("enolate ion") + "H"_2"O"#. Is HCl and NaOH an exothermic reaction? Hydrazine and hydroxylamine can also be used; they form a hydrazone and an oxime, respectively. 2. Step 2: Nucleophilic reaction by the enolate. Experts are tested by Chegg as specialists in their subject area. Synthesis of Ketones. My answer turns out to be an intermediate. This reaction requires quite a bit of heat (~200 deg C) and has been supplanted by milder methods. The additional stability provided by the conjugated carbonyl system of the product makes some aldol reactions thermodynamically driven and mixtures of stereoisomers (E & Z) are obtained from some reactions. A proton from the positively charged nitrogen is transferred to water, leading to the imine's formation. . Second, aldehydes lacking alpha-hydrogens can only function as acceptor reactants, and this reduces the number of possible products by half. and any corresponding bookmarks? Note: Benzylic oxidation requires the presence of a benzylic hydrogen, so no reaction occurs here: MnO2, heat: No Products Predicted. O 1) LDA (0.95 eq) / THF 2) CH3OTs3) MCPBA? Reactions with carboxylic acids. Q,) NaOH, H2O, heat. An organic compound (A) contains 87.27% C and 13.73% H. Its vapour density is 55. Figure 6. The major reaction would be E2. The AEMs of qBPBA-80-OQ-100 and qBPBA-80 have . 7.6) Simmons-Smith Reaction CH2I2, Zu(Cu) Syn addition . 3. Under Basic conditions 1) Nucleophilic attack by hydroxide 2) Protonation of the alkoxide Under Acidic conditions 1) Protonation of the carbonyl Page 16. Thus, a solution of formaldehyde in water (formalin) is almost exclusively the hydrate, or polymers of the hydrate. The mechanism proceeds as follows: 1. An unshared electron pair on the alcohol's oxygen atom attacks the carbonyl group. benzophenone is an aromatic ketone and its carbonyl stretching band has a lower wave number than Assuming no heat loss, calculate the final temperature of the water. Addition: Acetal/hemiacetal formation by alcohol .