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The Zeisel method is an old analytical procedure for determining the number of methoxyl groups in a compound. A weighed amount of the compound is heated with concentrated HI, ether cleavage occurs, and the iodomethane product is distilled off and passed into an alcohol solution of AgNO3, where it reacts to form a precipitate of silver iodide. The Agl is then collected and weighed, and the percentage of methoxyl groups in the sample is thereby determined. For example, 1.06 g of vanillin, the material responsible for the characteristic odor of vanilla, yields 1.60 g of Agl. If vanillin has a molecular weight of 152, how many methoxyl groups does it contain?
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Chapter 18 Solutions
Bundle: Organic Chemistry, Loose-leaf Version, 9th + LMS Integrated for OWLv2, 4 terms (24 months) Printed Access Card
- Wittig reactions with the following -chloroethers can be used for the synthesis of aldehydes and ketones. (a) Draw the structure of the triphenylphosphonium salt and Wittig reagent formed from each chloroether. (b) Draw the structural formula of the product formed by treating each Wittig reagent with cyclopentanone. Note that the functional group is an enol ether or, alternatively, a vinyl ether. (c) Draw the structural formula of the product formed on acid-catalyzed hydrolysis of each enol ether from part (b).arrow_forwardIn the workup of the grignard reaction of turning bromobenzene to benzoic acid, we start by mixing the grignard with HCl and diethyl ether. We discard the aqueous layer and wash the organic layer with water. Then, the organic layer is extracted with NaOH. Then, the extracts are heated to remove ether. Then, it is precipitated with HCl. Precipitate collected. Let it dry and finally, purified with toluene and hexanes. Please make a flowchart of the process of this workup indicating what products and byproducts are forming. And what compounds are in the aqueous layer and organic layer in the steps.arrow_forwardWhen CO2 is bubbled through a solution of benzyl magnesium bromide, and the mixture is then acidified, the product is phenylacetic acid. Any unreacted benzyl magnesium bromide is converted to toluene in the acidification step. 1. Write the complete reaction sequence for the process, showing product and byproduct. 2. How could you separate phenylacetic acid from toluene?arrow_forward
- Choose the best reagents from the list provided below for carrying out the following conversion. Match the reagent with the step number. HCl (aq), Zn(Hg) Br2, FeBr3 Na/NH3, -33 degrees C NBS, light KMnO4, H3O+ Mg metal, ether KOH, EtOH, heatarrow_forwardSpecify which compound from 2-methyl-2-butanol or 2-butanol and 1-Methylcyclopentanol or cyclohexanol compound pairs will convert to alkyl bromide faster with HBr. Write down the reactions for fast-converting alcoholsarrow_forwardFill in the appropriate reagents for the following reaction:arrow_forward
- Phineas and Ferbs, two brothers who enjoy vacations, doing fun things every summer. This summer the brothers and their friends carry out an organic synthesis with an unknown compound (L1) that contains 52% Carbon, 6% Hydrogen and 42% bromine, this compound (L1) is treated with magnesium in ether to obtain L2 , which reacts violently with D2O for 1-methyl cyclohexene with a deuterium atom in the methyl group (L3). The L2 reaction is treated with acetone followed by hydrolysis to give L4. Heating L4 with concentrated sulfuric acid gives L5, which decolors the bromine, obtaining L6. L5 undergoes hydrogenation with excess hydrogen and platinum as a catalyst giving rise to isobutyl cyclohexane. Determine the structures of compounds L1 through L6.arrow_forwardWhat aldehyde or ketone is needed to prepare each alcohol by metal hydride reduction?arrow_forwardDesribe the reaction product.arrow_forward
- Give the reagents and reaction conditions for the conversion of (i), (ii), (iii), (iv) and (v) CH3CH2Br ➡ A ➡ CH3COOH (i) (ii) A ➡ CH3CHO ➡ B ➡ CH3CH(OH)COOH (iii) (iv) (v) What type of reaction is step (i), (ii), (iii), & (iv).arrow_forwardPick the reactant or solvent in each part that gives the faster elimination reaction.a. reaction of -OH with 1-chloro-1-methylcyclohexane or 1-chloro-3-methylcyclohexaneb. reaction of H2O with CH3CH(Cl)CH2CH3 or (CH3)2C(Cl)CH2CH3c. reaction of (CH3)3CCl with -OH in H2O or DMSOarrow_forwardAlcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning