Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 19, Problem 89P
When heated with chromic acid, compound A forms benzoic acid. Identity compound A from its 1H NMR spectrum.
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1. Calculate the accurate monoisotopic mass (using all 1H, 12C, 14N, 160 and 35CI) for your product using the table in
your lab manual. Don't include the Cl, since you should only have [M+H]*. Compare this to the value you see on
the LC-MS printout. How much different are they?
2. There are four isotopic peaks for the [M+H]* ion at m/z 240, 241, 242 and 243. For one point of extra credit,
explain what each of these is and why they are present.
3. There is a fragment ion at m/z 184. For one point of extra credit, identify this fragment and confirm by
calculating the accurate monoisotopic mass.
4. The UV spectrum is also at the bottom of your printout. For one point of extra credit, look up the UV spectrum
of bupropion on Google Images and compare to your spectrum. Do they match? Cite your source.
5. For most of you, there will be a second chromatographic peak whose m/z is 74 (to a round number). For one
point of extra credit, see if you can identify this molecule as well and confirm by…
Please draw, not just describe!
can you draw each step on a piece of a paper please this is very confusing to me
Chapter 19 Solutions
Organic Chemistry
Ch. 19.1 - Draw the structure for each of the following: a....Ch. 19.2 - PROBLEM 2
If electrophilic addition to benzene is...Ch. 19.4 - Why does hydration inactivate FeBr3?Ch. 19.6 - Prob. 5PCh. 19.7 - Prob. 6PCh. 19.8 - What is the major product of a Friedel-Crafts...Ch. 19.10 - Describe two ways to prepare each of the following...Ch. 19.12 - Prob. 9PCh. 19.13 - Name the following:Ch. 19.13 - Prob. 12P
Ch. 19.13 - Prob. 13PCh. 19.13 - Prob. 14PCh. 19.14 - Prob. 15PCh. 19.14 - List the compounds in each set from most reactive...Ch. 19.15 - Prob. 18PCh. 19.15 - What product(s) result from nitration of each of...Ch. 19.15 - Prob. 20PCh. 19.16 - Which acid in each of the following pairs is...Ch. 19.16 - Prob. 23PCh. 19.16 - Prob. 24PCh. 19.18 - Show how the following compounds can be...Ch. 19.18 - Give the products, if any, of each of the...Ch. 19.19 - a. Does a coupling reaction have to be used to...Ch. 19.19 - PROBLEM 28
Show how each of the following...Ch. 19.20 - What is the major product(s) of each of the...Ch. 19.20 - Prob. 30PCh. 19.21 - Why isn't FeBr3 used as a catalyst in the first...Ch. 19.21 - Prob. 33PCh. 19.21 - Write the sequence of steps required for the...Ch. 19.21 - Prob. 35PCh. 19.22 - What product is formed from reaction of...Ch. 19.22 - Prob. 37PCh. 19.22 - Draw the structure of the activated ring and the...Ch. 19.23 - Prob. 39PCh. 19.23 - Prob. 40PCh. 19.23 - Diazomethane can be used to convert a carboxylic...Ch. 19.24 - Prob. 42PCh. 19.24 - Prob. 43PCh. 19.24 - Prob. 44PCh. 19.25 - Prob. 45PCh. 19 - Draw the structure for each of the following: a....Ch. 19 - Prob. 47PCh. 19 - Prob. 48PCh. 19 - Prob. 49PCh. 19 - For each of the statements in Column I, choose a...Ch. 19 - What product is obtained from the reaction of...Ch. 19 - Draw the product(s) of each of the following...Ch. 19 - Rank the following substituted anilines from most...Ch. 19 - Prob. 54PCh. 19 - The compound with the 1H NMR spectrum shown below...Ch. 19 - Prob. 56PCh. 19 - Show how the following compounds can be...Ch. 19 - Prob. 58PCh. 19 - Rank each group of compounds from most reactive to...Ch. 19 - Prob. 60PCh. 19 - Describe two ways to prepare anisole from benzene.Ch. 19 - For each of the following components, indicate the...Ch. 19 - Prob. 63PCh. 19 - Prob. 64PCh. 19 - Prob. 65PCh. 19 - Prob. 66PCh. 19 - An aromatic hydrocarbon with a molecular formula...Ch. 19 - The following tertiary alkyl bromides undergo an...Ch. 19 - Show how the following compounds can be...Ch. 19 - Use the four compounds shown below to answer the...Ch. 19 - a. Rank the following esters from most reactive to...Ch. 19 - A mixture of 0.10 mol benzene and 0.10 mol...Ch. 19 - Prob. 73PCh. 19 - Benzene underwent a Friedel-Crafts acylation...Ch. 19 - Prob. 75PCh. 19 - Prob. 76PCh. 19 - Prob. 77PCh. 19 - Friedel-Crafts alkylations can be carried out with...Ch. 19 - Show how the following compounds can be prepared...Ch. 19 - Prob. 80PCh. 19 - Prob. 81PCh. 19 - a. Describe four ways the following reaction can...Ch. 19 - Propose a mechanism for each of the following...Ch. 19 - Prob. 84PCh. 19 - Describe how naphthalene can he prepared from the...Ch. 19 - Prob. 86PCh. 19 - Using resonance contributors for the carbocation...Ch. 19 - Prob. 88PCh. 19 - When heated with chromic acid, compound A forms...Ch. 19 - Prob. 90PCh. 19 - Prob. 91PCh. 19 - What reagents are required to carry out the...Ch. 19 - Show how the following compounds can be prepared...Ch. 19 - An unknown compound reacts with ethyl chloride and...Ch. 19 - How can you distinguish the following compounds...Ch. 19 - P-Fluoronitrobenzene is more reactive toward...Ch. 19 - a. Explain why the following reaction leads to the...Ch. 19 - Describe how mescaline can be synthesized from...Ch. 19 - Propose a mechanism for the following reaction...Ch. 19 - Explain why hydroxide ion catalyzes the reaction...Ch. 19 - Propose a mechanism for each of the following...Ch. 19 - Prob. 102PCh. 19 - Prob. 103PCh. 19 - Describe how 3-methyl-1-phenyl-3-pentanol can he...Ch. 19 - a. How can aspirin be synthesized from benzene? b....Ch. 19 - Prob. 106PCh. 19 - Show how Novocain, a painkiller used frequently by...Ch. 19 - Prob. 108PCh. 19 - Saccharin, an artificial sweetener, is about 300...
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- > Can the molecule on the right-hand side of this organic reaction be made in good yield from no more than two reactants, in one step, by moderately heating the reactants? esc ? A O O •If your answer is yes, then draw the reactant or reactants in the drawing area below. You can draw the reactants in any arrangement you like. • If your answer is no, check the box under the drawing area instead. olo 18 Ar Explanation Check BB Click and drag to start drawing a structure. 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center Accessibilityarrow_forwardName the structurearrow_forward> For each pair of substrates below, choose the one that will react faster in a substitution reaction, assuming that: 1. the rate of substitution doesn't depend on nucleophile concentration and 2. the products are a roughly 50/50 mixture of enantiomers. Substrate A Substrate B Faster Rate X CI (Choose one) (Choose one) CI Br Explanation Check Br (Choose one) C 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy A F10arrow_forward
- How to draw this mechanism for the foloowing reaction in the foto. thank youarrow_forwardPredict the major products of the following organic reaction: Some important notes: CN A? • Draw the major product, or products, of the reaction in the drawing area below. • If there aren't any products, because no reaction will take place, check the box below the drawing area instead. • Be sure to use wedge and dash bonds when necessary, for example to distinguish between major products that are enantiomers. No reaction. Explanation Check Click and drag to start drawing a structure. 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use Privacy Centerarrow_forwardDraw the major product of the following reaction. Do not draw inorganic byproducts. H3PO4 OHarrow_forward
- Predict the major products of this organic reaction: HBr (1 equiv) Δ ? Some important notes: • Draw the major product, or products, of this reaction in the drawing area below. • You can draw the products in any arrangement you like. • Pay careful attention to the reaction conditions, and only include the major products. • Be sure to use wedge and dash bonds when necessary, for example to distinguish between major products that are enantiomers. • Note that there is only 1 equivalent of HBr reactant, so you need not consider the case of multiple additions. Explanation Check X ©2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacyarrow_forwardFor the structure below, draw the resonance structure that is indicated by the curved arrow(s). Be sure to include formal charges. :ÖH Modify the second structure given to draw the new resonance structure. Include lone pairs and charges in your structure. Use the + and - tools to add/remove charges to an atom, and use the single bond tool to add/remove double bonds.arrow_forwardUsing the table of Reactants and Products provided in the Hints section, provide the major product (with the correct stereochemistry when applicable) for questions below by selecting the letter that corresponds to the exact chemical structures for the possible product. OH conc Hydrochloric acid 40°C Temp A/arrow_forward
- Using arrows to designate the flow of electrons, complete the reaction below and provide a detailed mechanism for the formation of the product OH conc Hydrochloric acid 40°C Temp All chemical structures should be hand drawn on a piece of paper Paragraph BI UAE +varrow_forwarddraw out the following structures plesearrow_forwardDraw everything on a piece of paper outlining the synthesis from acetaldehyde to 2 cyclopentene carboxaldehyde using carbon based reagants with 3 carbons or fewers. Here is the attached image.arrow_forward
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