23.6 Intramolecular Aldol Reactions Treatment of certain dicarbonyl compounds with base produces cyclic products by intramolecular reaction CH₂ CH3 NaOH Ethanol CH₂ 2,5-Hexanedione 3-Methyl-2-cyclopentenone (a 1,4-diketone) 2,6-Heptanedione (a 1,5-diketone) + H₂O NaOH Ethanol CH3 + H₂O 3-Methyl-2-cyclohexenone
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- trehalose is a disacharide that can be obtained from fungi sea uchins and insects. acid hydrolysis of trehalose yields only D-glucose. trehalose is hydrolysed by a-glucosidase but not b-glucosidase.methylation of trhalose followed by hydrolysis yield two molar equivalents of 2-3-4-6 -tetra-O-methyl-D-glucopyranose. deduce the structure of the trehalose using the experimental dataTreatment with NaBH 4 converts aldose U into an optically inactive (meso) alditol V. Ruff degradation ofU gives W, whose alditol is optically inactive. Ruff degradation of W forms D-glyceraldehyde, thesimplest aldose. Upon Kiliani-Fischer synthesis, U is converted to two aldoses, X and Y. X is oxidized toan optically active aldaric acid Z. Y is oxidized to an optically inactive aldaric acid. Draw the structuresof D-glyceraldehyde, V, W, X, Y, and Z. Structure of compound U is shown below.Treatment with sodium borohydride converts aldose A to an optically inactive alditol. Wohl degradation of A forms B, whose alditol is optically inactive. Wohl degradation of B forms d-glyceraldehyde. Identify A and B.
- An optically active D-aldopentose (A) produced an optically inactive alditol (B) upon treatment with H2/Pt. When the aldopentose (A) was subjected to a Ruff degradation, D-aldotetrose (C) was generated. The aldotetrose (C) gave an optically active aldaric acid (D) upon oxidation with HNO3. D-aldopentose (A) can be prepared from D-threose by a Killani Fischer synthesis. Propose structure of A through D.All are true or false a)In solution, glucose is in the cyclic acetal form only. b)The driving force for the Wittig reaction is the elimination of triphenylphosphine oxide c)1H NMR spectroscopy, you can tell the difference between an aldehyde and a ketone because an aldehyde has a proton signal between 9–10 ppm. d)When an aldehyde is reacted with excess ethanol with an acid as a catalyst it is called hemiacetal e) You can't use acidic conditions (such as aqueous hydrochloric acid) for the addition of a Grignard reagent to a ketone because the ketone will be protonated and thus unreactiveDraw the product formed when phenylacetic acid (C6H5CH2COOH) istreated with following reagent. With some reagents, no reaction occurs. SOCl2
- Draw the product formed when phenylacetic acid (C6H5CH2COOH) istreated with following reagent. With some reagents, no reaction occurs. [1] SOCl2; [2] CH3CH2CH2NH2 (excess)2-Pentylcinnamaldehyde, commonly called flosal, is a perfume ingredient with a jasminelike odor. Flosal is an α,β-unsaturated aldehyde made by a crossed aldol reactionbetween benzaldehyde (C6H5CHO) and heptanal (CH3CH2CH2CH2CH2CH2CHO), followed by dehydration. Draw a stepwise mechanism for the following reaction that prepares flosal.As shown in Mechanism 29.2, the nal steps in the Edman degradation result in rearrangement of a thiazolinone to an Nphenylthiohydantoin. Draw a stepwise mechanism for this acid-catalyzed reaction.Mechanism 29.2: Edman Degradation
- The attached isomerization reaction, drawn using D-glucose as startingmaterial, occurs with all aldohexoses in the presence of base. Draw astepwise mechanism that illustrates how each compound is formed.Orsellinic acid, a common constituent of lichens, is synthesized from the condensation of acetyl thioester and malonyl thioester. If a lichen is grown on a medium containing acetate that was radioactively labeled with 14C at the carbonyl carbon, which carbons will be labeled in orsellinic acid?Identify the organic functional groups and reaction type for the following reaction.The reactant is a(n)a. beta pyranoseb. beta furanosec. alpha pyranosed. alpha furanoseThe product is a(n)a. alpha furanoseb. alpha pyranosec. beta furanosed. beta pyranoseThe reaction type is:a. oxidation (benedict's)b. esterificationc. mutarotationd. reduction (hydrogenation)e. hemiacetal formation