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)3 A (CH3)3COH 1. NaOEt, EtOH 1. NaOH, H,O C В 2. H,0º, A EtO OEt 2. Br(CH,),Br 100 90 80 70 60 – 50 40 - 30 20 C 4500 4000 3500 3000 2500 2000 1500 1000 500 200 175 150 125 100 75 50 25 Wavenumbers (cm-1) Chemical shift (ppm) % Transmittance

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)3 A (CH3)3COH 1. NaOEt, EtOH 1. NaOH, H,O C В 2. H,0º, A EtO OEt 2. Br(CH,),Br 100 90 80 70 60 – 50 40 - 30 20 C 4500 4000 3500 3000 2500 2000 1500 1000 500 200 175 150 125 100 75 50 25 Wavenumbers (cm-1) Chemical shift (ppm) % Transmittance

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

See similar textbooks

Similar questions

8. Using only ethylacetate, acetone, benzaldehyde, or benzyl bromide as organic components, and using any bases you desire, indicate a method to synthesize the following compounds: 요요 il
Determine if H₂O is a suitable reagent to protonate each of the two compounds shown below. 0° 0 Ⓒ1 = yes; II = no Ol=no; II = no I=no; II = yes. Ol=yes; II = yes O Not possible to determine with the information provided
Name this compound, including stereochemistry: Ho ÇH;CH;CH2OH H. Show the step(s) necessary to transform the compound on the left into the acid on the right. Benzyl alcohol benzoic acid Vhat are the products of the following reaction? H3O* -OCH3 Write in the product of this reaction: LIAIH4 N=CCHCH2CH3 CH3 Which type of spectroscopy (IR, 'H NMR, and/or C NMR) would be good to distinguish between benzoic acid and acetonitrile? State what you would observe for each compound in each type of spectroscopy and whether that type of spectroscopy would be a good way to distinguish between the two compounds.
What structure would best fit the following proton NMR data? NMR Data triplet 0.9 ppm (3H) hextet 1.5 ppm (2H) pentet 1.75 ppm (2H) triplet 3.25 ppm (2H) mutiple choice options 1-bromobutane 2-bromobutane 3-amino-1-propene 2-amino-1-propene
After treatment of phenol with sodium bicarbonate, the organic compound will be он NAHCO3 H2CO3 pKa 6.35 pKa -10 O in the ether layer O in the water layer O an ionic compound O not an ionic compound O!& 3 O 1& 4 O 2 & 3 O 2 & 4 O none of these
Carbon NMR Spectrum A has peaks at delta 71, 40, 19, and 12. Spectrum B has peaks at delta 72, 38, 31, 29, 22, 12, and 10. Which spectrum corresponds to 1-heptanol, and which corresponds to 4-heptanol. Explain your answer using structures.
22. Explain why the following compound cannot be converted to a Grignard reagent. How would you resolve this problem? O & Br O A dimer would form; treat C=0 with diol in acid Mg would react with C=0; treat C=0 with diol in acid A dimer would form; treat Br with diol in acid O Mg would react with C=0; treat Br with diol in acid MgBr
10-Bromo-a-chamigrene, a compound isolated from marine algae, is thought to be biosynthesized from y-bisabolene by the following route: "Br* Bromonium Cyclic carbocation -H*) Base ion Bromo peroxidase Br y-Bisabolene 10-Bromo-a- chamigrene
Answer questions a-c about the Bronsted acid-base reaction below using the identifying letters A-D below each structure. The pKa's for the acids of interest are: ethylammonium ion (pK = 10.8), and hydrogen chloride (pKa = -7). CH3- NH2 CH3. NH3 cī H-CI H2 A в D chloride ethylamine hydrogen chloride ethylammonium a) The stronger acid is b) Its conjugate base is c) The species that predominate at equilibrium are (two letters, e.g. ac)
5. Using the NMR and IR data, along with the molecular formula, provide structures for compounds A and B, along with the reagents needed to perform the transformation. → Compound A C5H10 NMR: 1.70 ppm, 3H, s 1.82 ppm, 3H, s 2.05 ppm, 3H, d 5.20 ppm, 1H, q IR: 3050 cm¹¹, m 2900 cm¹¹, s 1650 cm¹¹, m Compound B C5H₁1Br NMR: 0.90 ppm, 3H, t 1.75 ppm, 2H, q 1.84 ppm, 6H, s IR: 2950 cm¹¹, s 2900 cm¹¹, s 1450 cm¹, s
11. Provide a structure for Compound A, (C&H100), based on its IR and NMR spectra. Show full analysis of both the IR and NMR spectra. 8 82.1 2.34 3.7 7.2 B 40 20 4000 NMR: environ. 3304 Ratio 1H, 2H, 2H, 5 H, M 3015 2981 #H spl pat. broad singlet triplet triplet multiplet 2000 #nei. 1610 1900 Pieces
From each pair, select the stronger base. Then draw the conjugate acid of the strong base below. CH3CH20 or CH3CEC • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • You do not have to include lone pairs in your answer. C opy aste