Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 29, Problem 29.4P
Interpretation Introduction
Interpretation: The zwitterionic form of L-thyroxine is to be drawn.
Concept introduction: Amino acids are naturally occurring compounds in which the amino group is present on the
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Aspirin is the common name for the compound acetylsalicylic acid, widely used as a
fever reducer and as a pain killer. Salicylic acid, whose name comes from Salix, the
willow family of plants, was derived from willow bark extracts. In folk medicine, willow
bark teas were used as headache remedies and other tonics. Nowadays, salicylic acid
is administered in the form of aspirin which is less irritating to the stomach than salicylic
acid. To prepare aspirin, salicylic acid is reacted with an excess of acetic anhydride.
A small amount of a strong acid is used as a catalyst which speeds up the reaction. In
this experiment, phosphoric acid will be used as the catalyst. The excess acetic acid
will be quenched with the addition of water. The aspirin product is not very soluble in
water so the aspirin product will precipitate when water is added. The synthesis
reaction of aspirin is shown below:
Actic anhydride
5 ml.
Acetic acid
Salicylic acid
28
Acetylsalicylie acid
Procedure
1)
Mix salicylic…
1
2
3
4
Draw The
Structures?
Z-Butenedioic acid
(maleic acid)
2,5-Dimethylbenzoic acid
Z-2-Chloro-3-phenyl-2-
propenoic acid (cis-B-
chloroallocinnamic acid)
Decanedioic acid (sebacic
acid)
E-3-Phenyl-2-propenoic acid
(trans-cinnamic acid)
Using the data in Appendix C, determine which of the following bases is strong enough to deprotonate acetonitrile (CH3CN), so that equilibrium favors the products: (a) NaH; (b) Na2CO3; (c) NaOH; (d) NaNH2; (e) NaHCO3.
Chapter 29 Solutions
Organic Chemistry
Ch. 29 - Prob. 29.1PCh. 29 - Problem 29.2
What form exists at the isoelectric...Ch. 29 - Problem 29.3
Explain why the of the group of an...Ch. 29 - Prob. 29.4PCh. 29 - Problem 29.5
What -halo carbonyl compound is...Ch. 29 - Problem 29.6
The enolate derived from diethyl...Ch. 29 - Problem 29.7
What amino acid is formed when is...Ch. 29 - Problem 29.8
What aldehyde is needed to synthesize...Ch. 29 - Problem 29.9
Draw the products of each...Ch. 29 - Prob. 29.10P
Ch. 29 - Prob. 29.11PCh. 29 - Prob. 29.12PCh. 29 - Problem 29.13
What alkene is needed to synthesize...Ch. 29 - Problem 29.14
Draw the structure of each peptide....Ch. 29 - Problem 29.15
Name each peptide using both the...Ch. 29 - Prob. 29.16PCh. 29 - Prob. 29.17PCh. 29 - Problem 29.18
Glutathione, a powerful antioxidant...Ch. 29 - Problem 29.19
Draw the structure of the...Ch. 29 - Problem 29.20
Give the amino acid sequence of an...Ch. 29 - a What products are formed when each peptide is...Ch. 29 - Prob. 29.22PCh. 29 - Devise a synthesis of each peptide from amino acid...Ch. 29 - Devise a synthesis of the following dipeptide from...Ch. 29 - Prob. 29.25PCh. 29 - Consider two molecules of a tetrapeptide composed...Ch. 29 - What types of stabilizing interactions exist...Ch. 29 - Prob. 29.28PCh. 29 - Draw the product formed when the following amino...Ch. 29 - With reference to the following peptide: a...Ch. 29 - Devise a synthesis of the following dipeptide from...Ch. 29 - Prob. 29.32PCh. 29 - Histidine is classified as a basic amino acid...Ch. 29 - Tryptophan is not classified as a basic amino acid...Ch. 29 - What is the structure of each amino acid at its...Ch. 29 - What is the predominant form of each of the...Ch. 29 - 29.37 What is the predominant form of each of the...Ch. 29 - a. Draw the structure of the tripeptide A–A–A, and...Ch. 29 - 29.39 Draw the organic products formed in each...Ch. 29 - 29.40 What alkyl halide is needed to synthesize...Ch. 29 - 29.41 Devise a synthesis of threonine from diethyl...Ch. 29 - 29.42 Devise a synthesis of each amino acid from...Ch. 29 - Prob. 29.43PCh. 29 - Prob. 29.44PCh. 29 - Prob. 29.45PCh. 29 - Prob. 29.46PCh. 29 - Prob. 29.47PCh. 29 - 29.48 Brucine is a poisonous alkaloid obtained...Ch. 29 - Prob. 29.49PCh. 29 - Prob. 29.50PCh. 29 - Draw the structure for each peptide: (a) Phe–Ala;...Ch. 29 - 29.52 For the tetrapeptide Asp–Arg–Val–Tyr:
a....Ch. 29 - Prob. 29.53PCh. 29 - Prob. 29.54PCh. 29 - 29.55 Draw the amino acids and peptide fragments...Ch. 29 - Prob. 29.56PCh. 29 - Prob. 29.57PCh. 29 - Prob. 29.58PCh. 29 - 29.59 An octapeptide contains the following amino...Ch. 29 - 29.60 Draw the organic products formed in each...Ch. 29 - Draw all the steps in the synthesis of each...Ch. 29 - 29.62 Write out the steps for the synthesis of...Ch. 29 - 29.63 Besides the Boc and Fmoc protecting groups...Ch. 29 - 29.64 Another method to form a peptide bond...Ch. 29 - 29.65 Draw the mechanism for the reaction that...Ch. 29 - 29.66 Which of the following amino acids are...Ch. 29 - 29.67 After the peptide chain of collagen has been...Ch. 29 - Prob. 29.68PCh. 29 - Prob. 29.69PCh. 29 - 29.70 The anti-obesity drug orlistat works by...Ch. 29 - Prob. 29.71P
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- When the conjugate acid of aniline, C6H5NH3+, reacts with the acetate ion, the following reaction takes place: C6H5NH3+(aq)+CH3COO(aq)C6H5NH2(aq)+CH3COOH(aq) If Kafor C6H5NH3+ is 1.35105 and Kafor CH3COOH is 1.86105 , what is K for the reaction?arrow_forwardSalsalate, which is an ester formed by the reaction of two molecules of salicylic acid, is another salicylate used as an aspirin alternative for those who are hypersensitive to aspirin. Draw the structures of salicylic acid and salsalate.arrow_forwardBecause amines are basic, they can often accept a proton. Draw the protonated structure of n-propylamine.arrow_forward
- Indinavir (trade name Crixivan) is a drug used to treat HIV. (a) At which sites can indinavir hydrogen bond to another molecule like itself? (b) At which sites can indinavir hydrogen bond to water?arrow_forwardFurosemide is a diuretic medication used to treat patients with congestive heart failure (CHF). It can treat fluid retention caused by CHF, liver disease or kidney failure. Please refer to the structure of Furosemide drawn below to answer the next five questionsarrow_forwardWhen hexanoic acid (a carboxlic acid) is heated, a reaction takes place that generates water (which must be removed) and a non-acidic product. What is the product? carboxylate carboxylic acid anhydride ester amide lies! all lies! no reaction will take place!arrow_forward
- Stanozolol is an anabolic steroid that promotes muscle growth. Althoughstanozolol has been used by athletes and body builders, many physicaland psychological problems result from prolonged use and it is bannedin competitive sports. Explain why the pKa of the N—H bond in the pyrazole ring iscomparable to the pKa of the O—H bond, making it considerably moreacidic than amines such as CH3NH2 (pKa = 40).arrow_forwardWhich type of amine is phentermine? a) a primary aliphatic amine b) a primary aromatic amine c) a tertiary aliphatic amine d) a tertiary aromatic aminearrow_forwardDraw the structures of aspirin, caffeine, and acetaminophen. Give the hybridization of each carbon atom and state which is acidic, weakly acidic, and basic. Identify the sites on each compound that make each acidic, weakly acidic, and basic.arrow_forward
- 2. Draw in the product (or products) formed from the acidic hydrolysis of the following compound. ^^ Hydrolysisarrow_forwardFollowing is the structure of unoprostone, a compound patterned after the natural prostaglandins antiglaucoma drug used to treat ocular hypertension. Compare the structural formula of this synthetic prostaglandin with that of PGF . Rescula, the isopropyl ester of unoprostone, is an НО COOH CH3 НО Unoprostone (antiglaucoma)arrow_forwardare involved in the regulation of glucose metabolism and in control tissue swelling by the control of inflammation, while regulating cellular salt balance between Na+ and K+. a.glucocorticoids, mineralocorticoids b. mineralocorticoids, glucocorticoids c. androgen, estrogen d. estrogen, androgen Which of the following represents an aldonic acid? OH OH но, но OH но —н но Но HO HO H но но H H- -OH -OH H OH H FOH H- -OH- OH HO но HO. OH II III IV V Refer to the structures. Which of the following compounds will react with acetyl chloride to give an amide and ester, respectively? NH2 ÇOOH CH3 он CHO II II IV V The six groups of enzymes are the following: I. Oxidoreductases II. Transferases III. Hydrolases IV. Isomerases V. Lyases VI. Ligases Fill in the blanks: catalyze hydrolysis while catalyze bond formation.arrow_forward
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