Connect 1-Semester Online Access for Principles of General, Organic & Biochemistry
2nd Edition
ISBN: 9780077633707
Author: Janice Smith
Publisher: Mcgraw-hill Higher Education (us)
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Textbook Question
Chapter 16, Problem 16.38AP
Why is phenylalanine water soluble but 4-phenylbutanoic acid (C6H5CH2CH2CH2COOH), a compound of similar molecular weight, water insoluble?
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Complete the following table. The only density needed is already given. Show your
calculations in a neat and easy-to-follow manner in the space below the table. All units
should be included and significant figures should be given close attention. Be sure to notice
that the amount of material should be in millimoles rather than moles, and the theoretical
mass of the product should in milligrams rather than grams.
LOCH 3
+
H2SO4
HNO 3
O=C-OCH 3
NO2
x
H₂O
F.W.
4.0 mL 1.3 M
amount
0.50 mL
in H2SO4
mg Theoretical
Theoretical
mmoles
density
1.09
Kumada Coupling:
1. m-Diisobutylbenzene below could hypothetically be synthesized by Friedel-Crafts reaction. Write out the reaction with a
mechanism and give two reasons why you would NOT get the desired product.
Draw the reaction (NOT a mechanism) for a Kumada coupling to produce the molecule above from m-dichlorobenzene.
Calculate the theoretical yield for the reaction in question 2 using 1.5 g of p-dichlorobenzene and 3.0 mL isobutyl bromide.
What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What
other impurities are present in your product and how do you know?
Wintergreen from Aspirin:
1. In isolating the salicylic acid, why is it important to press out as much of the water as possible?
2. Write the mechanism of the esterification reaction you did.
3.
What characteristic absorption band changes would you expect in the IR spectrum on going from aspirin to salicyclic acid and
then to methyl salicylate as you did in the experiment today? Give approximate wavenumbers associated with each functional
group change.
What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What
other impurities are present in your product and how do you know?
Chapter 16 Solutions
Connect 1-Semester Online Access for Principles of General, Organic & Biochemistry
Ch. 16.2 - In addition to the amino and carboxyl groups, what...Ch. 16.2 - How do the OH groups in Ser, Thr, and Tyr differ?Ch. 16.2 - Draw both enantiomers of each amino acid in...Ch. 16.2 - Which of the following amino acids is naturally...Ch. 16.3 - Draw the structure of the amino acid valine at...Ch. 16.3 - Identify the amino acid shown with all uncharged...Ch. 16.3 - Draw the positively charged, neutral, and...Ch. 16.4 - Identify the N-terminal and C-terminal amino acid...Ch. 16.4 - (a) Identify the N-terminal amino acid in the...Ch. 16.4 - Identify the individual amino acids in each...
Ch. 16.4 - Prob. 16.11PCh. 16.5 - Prob. 16.12PCh. 16.6 - Prob. 16.13PCh. 16.6 - Draw the structures of each pair of amino acids...Ch. 16.6 - The fibroin proteins found in silk fibers consist...Ch. 16.7 - Prob. 16.16PCh. 16.7 - Prob. 16.17PCh. 16.8 - Prob. 16.18PCh. 16.8 - Prob. 16.19PCh. 16.8 - Prob. 16.20PCh. 16.9 - Prob. 16.21PCh. 16.9 - Prob. 16.22PCh. 16.9 - The nerve gas sarin acts as a poison by covalently...Ch. 16.10 - Prob. 16.24PCh. 16 - Prob. 16.25UKCCh. 16 - Prob. 16.26UKCCh. 16 - For each amino acid: [1] draw the L enantiomer in...Ch. 16 - For each amino acid: [1] give the name; [2] give...Ch. 16 - For the given tripeptide: (a) identify the amino...Ch. 16 - For the given tripeptide: (a) identify the amino...Ch. 16 - Label the regions of secondary structure in the...Ch. 16 - Label the regions of secondary structure in the...Ch. 16 - What type of interactions occur at each of the...Ch. 16 - Using the given representations for an enzyme and...Ch. 16 - Naturally occurring amino acids are L--amino...Ch. 16 - Why do neutral amino acids exist as zwitterions...Ch. 16 - The amino acid alanine is a solid at room...Ch. 16 - Why is phenylalanine water soluble but...Ch. 16 - Draw the structure of a naturally occurring amino...Ch. 16 - Draw the structure of a naturally occurring amino...Ch. 16 - For each amino acid: [1] draw the l enantiomer in...Ch. 16 - For each amino acid: [1] draw the l enantiomer in...Ch. 16 - Draw both enantiomers of each amino acid and label...Ch. 16 - Which of the following Fischer projections...Ch. 16 - For each amino acid: [1] give the name; [2] give...Ch. 16 - For each amino acid: [1] give the name; [2] give...Ch. 16 - Draw the amino acid leucine at each pH: (a) 6; (b)...Ch. 16 - Draw the amino acid isoleucine at each pH: (a) 6;...Ch. 16 - Draw the structure of the neutral, positively...Ch. 16 - Draw the structure of the neutral, positively...Ch. 16 - For each tripeptide: [1] identify the N-terminal...Ch. 16 - For each tripeptide: [1] identify the N-terminal...Ch. 16 - For the given tripeptide: (a) identify the amino...Ch. 16 - For the given tripeptide: (a) identify the amino...Ch. 16 - Locate the peptide bond in the dipeptide shown in...Ch. 16 - Label the N-terminal and C-terminal amino acids in...Ch. 16 - Draw the structures of the amino acids formed when...Ch. 16 - Draw the structures of the amino acids formed when...Ch. 16 - What amino acids are formed by hydrolysis of the...Ch. 16 - Give the three-letter abbreviations for the amino...Ch. 16 - What is the difference between the primary and...Ch. 16 - What is the difference between the tertiary and...Ch. 16 - What type of intermolecular forces exist between...Ch. 16 - Which of the following pairs of amino acids can...Ch. 16 - List two amino acids that would probably be...Ch. 16 - List two amino acids that would probably be...Ch. 16 - Compare -keratin and hemoglobin with regards to...Ch. 16 - Compare collagen and myoglobin with regards to...Ch. 16 - When a protein is denatured, how is its primary,...Ch. 16 - Hydrogen bonding stabilizes both the secondary and...Ch. 16 - Describe the function or biological activity of...Ch. 16 - Describe the function or biological activity of...Ch. 16 - Use the given representations for an enzyme,...Ch. 16 - Use the given representations for an enzyme and...Ch. 16 - How are enzyme inhibitors used to treat high blood...Ch. 16 - How are enzyme inhibitors used to treat HIV? Give...Ch. 16 - What structural feature in -keratin makes...Ch. 16 - Why does the -keratin in hair contain many...Ch. 16 - Why must vegetarian diets be carefully balanced?Ch. 16 - Why does cooking meat make it easier to digest?Ch. 16 - Sometimes an incision is cauterized (burned) to...Ch. 16 - Prob. 16.82APCh. 16 - How is sickle cell disease related to hemoglobin...Ch. 16 - The silk produced by a silkworm is a protein with...Ch. 16 - Explain the difference in the mechanism of action...Ch. 16 - How are blood enzyme levels used to diagnose...Ch. 16 - Explain why two amino acids aspartic acid and...Ch. 16 - Prob. 16.88CP
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- Synthesis of ZybanⓇ: 1. Write a mechanism for the bromination of m-chloropropiophenone. Br₂ CH2Cl2 Cl Br 2. Give the expected m/z (to a round number) for the molecular ion from the product above (including isotopic peaks). 3. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardSynthesis of Ibuprofen-Part 2: 1. Some pain relievers including ibuprofen (MotrinⓇ) and naproxen (Aleve®) are "α-arylpropanoic acids." Look up the structure of naproxen (AleveⓇ), another a-arylpropionic acid. Using the same reactions that we used for making ibuprofen, show how to make naproxen from the compound below. Show all intermediates and reagents in your synthesis. Show how you would prepare ibuprofen starting from p-isobutylbenzene rather than p-isobutylacetophenenone. What reaction steps would need to change/add? 3. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardAcid Catalyzed Aromatization of Carvone: 1. Starting with the ketone, below, draw a mechanism for the reaction to give the phenol as shown. H2SO4 HO- H₂O 2. Why do we use CDCl instead of CHCl, for acquiring our NMR spectra? 3. Why does it not matter which enantiomer of carvone is used for this reaction? What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forward
- Assign this H NMRarrow_forwardPlease complete these blanks need that asaparrow_forwardNitration of Methyl Benzoate: 1. Predict the major product for the reaction below AND provide a mechanism. Include ALL resonance structures for the intermediate. C(CH3)3 NO₂* ? 2. Assuming the stoichiometry is 1:1 for the reaction above, what volume of concentrated nitric acid would be required to mononitrate 0.50 grams of the compound above? What product(s) might you expect if you nitrated phenol instead of methyl benzoate? Explain your reasoning. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forward
- Sodium Borohydride Reduction (continued on the next page): 1. Draw the product of each of the reactions below and give the formula mass to the nearest whole number. ? (1) NaBH (2) acid (1) NaBD4 (2) acid ? 2. In mass spectra, alcohols typically break as shown in equation 8 in chapter 11 (refer to your lab manual). The larger group is generally lost and this gives rise to the base peak in the mass spectrum. For the products of each of the reactions in question # 1, draw the ion corresponding to the base peak for that product and give its mass to charge ratio (m/z). 3. Given the reaction below, calculate how many mg of 1-phenyl-1-butanol that can be produced using 31 mg NaBH4 and an excess of butyrophenone. 4. + NaBH4 OH (after workup with dilute HCI) What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardAspirin from Wintergreen: 1. In isolating the salicylic acid, why is it important to press out as much of the water as possible? Write a step-by-step mechanism for the esterification of salicylic acid with acetic anhydride catalyzed by concentrated H₂SO4. 3. Calculate the exact monoisotopic mass of aspirin showing your work. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardSynthesis of Ibuprofen-Part 1: 1. What characteristic absorption band changes would you expect in the IR spectrum on going from p-isobutylacetophenone to 1-(4-isobutylphenyl)-ethanol and then to 1-(4-isobutylphenyl)-1-choroethane as you did in the experiment today? Give approximate wavenumbers associated with each functional group change. Given that the mechanism of the chlorination reaction today involves formation of a benzylic carbocation, explain why the following rearranged product is not formed. محرم محمد 3. Why do we use dilute HCl for the first step of the reaction today and concentrated HCI for the second step? What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forward
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