(a)
Interpretation:
The complete, detailed mechanism and the overall product for the given reaction is to be drawn.
Concept introduction:
The ester is hydrolyzed to the
![Check Mark](/static/check-mark.png)
Answer to Problem 21.14P
The mechanism and product for the given reaction is:
Explanation of Solution
In Step 1 of the mechanism, the acid protonates the ester’s carbonyl group, and in Step 2, water attacks the carbonyl
The complete, detailed mechanism and the overall product for the given reaction is drawn by acid-catalyzed ester hydrolysis.
(b)
Interpretation:
The complete, detailed mechanism and the overall product for the given reaction is to be drawn.
Concept introduction:
This is an acid-catalyzed transesterification, and a new ester is formed.
![Check Mark](/static/check-mark.png)
Answer to Problem 21.14P
The mechanism and product for the given reaction is:
Explanation of Solution
In Step 1 of the mechanism, the acid protonates the ester’s carbonyl group, and in Step 2,
The complete, detailed mechanism and the overall product for the given reaction is drawn by acid-catalyzed transesterification.
(c)
Interpretation:
The complete, detailed mechanism and the overall product for the given reaction is to be drawn.
Concept introduction:
This is an acid catalyzed amide hydrolysis which produces a carboxylic acid. Water acts as the nucleophile in this acid-catalyzed nucleophilic addition–elimination mechanism, and the leaving group is a molecule of
![Check Mark](/static/check-mark.png)
Answer to Problem 21.14P
The mechanism and product for the given reaction is:
Explanation of Solution
In Step 1 of the mechanism, the acid protonates the ester’s carbonyl group, and in Step 2, water attacks the carbonyl
The complete, detailed mechanism and the overall product for the given reaction is drawn by acid-catalyzed amide hydrolysis.
(d)
Interpretation:
The complete, detailed mechanism and the overall product for the given reaction is to be drawn.
Concept introduction:
This is an acid catalyzed ester hydrolysis which produces a carboxylic acid. Water acts as the nucleophile in this acid-catalyzed nucleophilic addition–elimination mechanism, and the leaving group is a molecule of alcohol. Proton transfer steps are incorporated to avoid the appearance of strong bases.
![Check Mark](/static/check-mark.png)
Answer to Problem 21.14P
The mechanism and product for the given reaction is:
Explanation of Solution
In Step 1 of the mechanism, the acid protonates the ester’s carbonyl group, and in Step 2, water attacks the carbonyl
The complete, detailed mechanism and the overall product for the given reaction is drawn by acid-catalyzed ester hydrolysis.
(e)
Interpretation:
The complete, detailed mechanism and the overall product for the given reaction is to be drawn.
Concept introduction:
This is Fischer esterification reaction.
![Check Mark](/static/check-mark.png)
Answer to Problem 21.14P
The mechanism and product for the given reaction is:
Explanation of Solution
In Step 1 of the mechanism, the acid protonates the acid’s carbonyl group, and in Step 2,
The complete, detailed mechanism and the overall product for the given reaction is drawn by Fischer esterification reaction.
(f)
Interpretation:
The complete, detailed mechanism and the overall product for the given reaction is to be drawn.
Concept introduction:
This is an acid catalyzed amide hydrolysis which produces a carboxylic acid. Water acts as the nucleophile in this acid-catalyzed nucleophilic addition–elimination mechanism, and the leaving group is a molecule of amine. Proton transfer steps are incorporated to avoid the appearance of strong bases.
![Check Mark](/static/check-mark.png)
Answer to Problem 21.14P
The mechanism and product for the given reaction is:
Explanation of Solution
In Step 1 of the mechanism, the acid protonates the ester’s carbonyl group, and in Step 2, water attacks the carbonyl
The complete, detailed mechanism and the overall product for the given reaction is drawn by acid-catalyzed amide hydrolysis.
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Chapter 21 Solutions
EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
- Use the References to access important values if needed for this question. What is the IUPAC name of each of the the following? 0 CH3CHCNH₂ CH3 CH3CHCNHCH2CH3 CH3arrow_forwardYou have now performed a liquid-liquid extraction protocol in Experiment 4. In doing so, you manipulated and exploited the acid-base chemistry of one or more of the compounds in your mixture to facilitate their separation into different phases. The key to understanding how liquid- liquid extractions work is by knowing which layer a compound is in, and in what protonation state. The following liquid-liquid extraction is different from the one you performed in Experiment 4, but it uses the same type of logic. Your task is to show how to separate apart Compound A and Compound B. . Complete the following flowchart of a liquid-liquid extraction. Handwritten work is encouraged. • Draw by hand (neatly) only the appropriate organic compound(s) in the boxes. . Specify the reagent(s)/chemicals (name is fine) and concentration as required in Boxes 4 and 5. • Box 7a requires the solvent (name is fine). • Box 7b requires one inorganic compound. • You can neatly complete this assignment by hand and…arrow_forwardb) Elucidate compound D w) mt at 170 nd shows c-1 stretch at 550cm;' The compound has the ff electronic transitions: 0%o* and no a* 1H NMR Spectrum (CDCl3, 400 MHz) 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 13C{H} NMR Spectrum (CDCl3, 100 MHz) Solvent 80 70 60 50 40 30 20 10 0 ppm ppm ¹H-13C me-HSQC Spectrum ppm (CDCl3, 400 MHz) 5 ¹H-¹H COSY Spectrum (CDCl3, 400 MHz) 0.5 10 3.5 3.0 2.5 2.0 1.5 1.0 10 15 20 20 25 30 30 -35 -1.0 1.5 -2.0 -2.5 3.0 -3.5 0.5 ppm 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppmarrow_forward
- Part I. a) Elucidate the structure of compound A using the following information. • mass spectrum: m+ = 102, m/2=57 312=29 • IR spectrum: 1002.5 % TRANSMITTANCE Ngg 50 40 30 20 90 80 70 60 MICRONS 5 8 9 10 12 13 14 15 16 19 1740 cm M 10 0 4000 3600 3200 2800 2400 2000 1800 1600 13 • CNMR 'H -NMR Peak 8 ppm (H) Integration multiplicity a 1.5 (3H) triplet b 1.3 1.5 (3H) triplet C 2.3 1 (2H) quartet d 4.1 1 (2H) quartet & ppm (c) 10 15 28 60 177 (C=0) b) Elucidate the structure of compound B using the following information 13C/DEPT NMR 150.9 MHz IIL 1400 WAVENUMBERS (CM-1) DEPT-90 DEPT-135 85 80 75 70 65 60 55 50 45 40 35 30 25 20 ppm 1200 1000 800 600 400arrow_forward• Part II. a) Elucidate The structure of compound c w/ molecular formula C10 11202 and the following data below: • IR spectra % TRANSMITTANCE 1002.5 90 80 70 60 50 40 30 20 10 0 4000 3600 3200 2800 2400 2000 1800 1600 • Information from 'HAMR MICRONS 8 9 10 11 14 15 16 19 25 1400 WAVENUMBERS (CM-1) 1200 1000 800 600 400 peak 8 ppm Integration multiplicity a 2.1 1.5 (3H) Singlet b 3.6 1 (2H) singlet с 3.8 1.5 (3H) Singlet d 6.8 1(2H) doublet 7.1 1(2H) doublet Information from 13C-nmR Normal carbon 29ppm Dept 135 Dept -90 + NO peak NO peak 50 ppm 55 ppm + NO peak 114 ppm t 126 ppm No peak NO peak 130 ppm t + 159 ppm No peak NO peak 207 ppm по реак NO peakarrow_forwardCould you redraw these and also explain how to solve them for me pleasarrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
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