21.95 A student carries out the following sequence of reactions. The IR and 1°C NMR spectra are shown for the product C.Draw structures for A-C. (Remember that the 13C NMR signal at 77 ppm is due to the CDCI3 solvent.)NaOC(CH)3A(CH3)3COH1. NaOEt, EtOH1. NaOH, H,OCВ2. H,0º, AEtOOEt2. Br(CH,),Br10090807060 –5040 -3020C4500 4000 3500 3000 2500 2000 1500 1000 500200175150125100755025Wavenumbers (cm-1)Chemical shift (ppm)% Transmittance

The compound malonic ester is denoted as the presence of two ester groups (-COOC2H5) bonded directly…

Answered: 21.95 A student carries out the…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter24: Amines And Heterocycles

Section24.10: Spectroscopy Of Amines

Problem 25P

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Rhodamine B is useful dye prepared in a manner very similar to fluorescein. Due to the nitrogen donating groups, rhodamine B absorbs 550 nm light and fluoresces 580 nm light. Provide a detailed mechanism for the formation of Rhodamine B from m-(diethylamino)phenol and phthalic anhydride in the presence of acid and heat.
Several sulfonylureas, a class of compounds containing RSO2NHCONHR, are useful drugs as orally active replacements for injected insulin in patients with adult-onset diabetes. These drugs decrease blood glucose concentrations by stimulating b cells of the pancreas to release insulin and by increasing the sensitivity of insulin receptors in peripheral tissues to insulin stimulation. Tolbutamide is synthesized by the reaction of the sodium salt of p-toluenesulfonamide and ethyl N-butylcarbamate . Propose a mechanism for this step.
Acid-catalyzed hydrolysis of HOCH2CH2C(CH3)2CN forms compound A (C6H10O2). A shows a strong peak in its IR spectrum at 1770 cm-1 and the following signals in its 1H NMR spectrum: 1.27 (singlet, 6 H), 2.12 (triplet, 2 H), and 4.26 (triplet, 2 H) ppm. Draw the structure for A and give a stepwise mechanism that accounts for its formation.
17.36 Tamoxifen is an estrogen receptor modulator that is used in the treatment of breast cancer. Provide the missing reagents and the structure of compound A in the synthesis of tamoxifen. Page 707 HO (CH3)2N 1. C,H,MgBr 2. H + Compound A (CH3)2N Tamoxifen
Compound A is a derivative of the carbohydrate perosamine, which is found in the antibiotic perimycin. When A is treated with acetic anhydride in methanol, a monoacyl derivative B (C9H17NO5) is obtained in 73% yield. What is the structure of compound B?
The treatment of isoprene [CH2 = C(CH3)CH = CH2] with one equivalent of mCPBA forms A as the major product. A gives a molecular ion at 84 in its mass spectrum, and peaks at 2850–3150 cm−1 in its IR spectrum. The 1H NMR spectrum of A is given below. What is the structure of A?
(a) Explain the mechanism of a nucleophilic attack on the carbonyl group of an aldehyde or a ketone.(b) An organic compound (A) (molecular formula CgH16Q2) was hydrolysed with dilute sulphuric acid to give a carboxylic acid (B) and an alcohol (C). Oxidation of (C) with chromic acid also produced (B). On dehydration (C) gives but-1-ene. Write the equations for the reactions involved.
1. The ketone 2-heptanone has been identified as contributing to the odor of a number of dairy products, including condensed milk and cheddar cheese. Describe the synthesis of 2-heptanone from acetylene and any necessary organic and inorganic reagents. 2. Compound A has the molecular formula C14H25Br and was obtained by reaction of sodium acetylide (HC≡CNa) )with 1,12-dibromododecane. On treatment of compound A with sodium amide, it was converted to compound B (C14H24). Ozonolysis of compound B gave the diacid HO2C(CH2)12CO2H. Catalytic hydrogenation of compound B over Lindlar palladium gave compound C (C14H26), while hydrogenation over platinum gave compound D (C14H28). Sodium-ammonia reduction of compound B gave compound E (C14H26). Both C and E yielded O═CH(CH2)12CH═O on ozonolysis. Assign structures to compound A through E so as to be consistent with the observed transformations.
An ether extraction of nutmeg gives large quantities of trimyristin, a waxy crystalline solid of melting point 57 °C. The IRspectrum of trimyristin shows a very strong absorption at 1733 cm-1. Basic hydrolysis of trimyristin gives 1 equivalent ofglycerol and 3 equivalents of myristic acid (tetradecanoic acid).(a) Draw the structure of trimyristin.(b) Predict the products formed when trimyristin is treated with lithium aluminum hydride, followed by aqueous hydrolysis of the aluminum salts
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