Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 29, Problem 29.40P
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What alkene is needed to synthesize each amino acid by an enantioselective hydrogenation reaction using H2 and Rh*: (a) alanine; (b) leucine; (c) glutamine?
What alkyl halide is needed to synthesize each amino acid from diethyl acetamidomalonate: (a) Asn; (b) His; (c) Trp?
Draw the product formed when the following amino acid is treated with each reagent: (a) CH3OH, H+; (b) CH3COCl, pyridine; (c) HCl (1 equiv); (d) NaOH (1 equiv); (e) C6H5N=C=S.
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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- 2. Classify the following amino acids as nonpolar, polar basic, polar acidic, or polar neutral. (a) (b) (c) (d) H₂N-CH-COH CH-OH I CH3 || H₂N-CH-C-OH I CH₂ C=O 1 OH H₂N-CH-C-OH CH₂ T CH-CH3 CH₂ H₂N-CH-C-OH ī CH₂ OH 229arrow_forwardDraw the amino acids and peptide fragments formed when the decapeptide A–P–F–L–K–W–S–G–R–G is treated with each reagent or enzyme: (a) chymotrypsin; 8 pt helvetica roman (b) trypsin; (c) carboxypeptidase; (d) C6H5N = C = S.arrow_forwardDraw the product formed when the following amino acid is treated with each reagent: (a) CH3OH, H+; (b) CH3COCCl, pyridine; (c) HCl (1 equiv); (d) NaOH (1 equiv); (e) C6H5N = C = S.arrow_forward
- 8arrow_forwardDraw both enantiomers of each amino acid and label them as R or S: (a) phenylalanine; (b) methionine.arrow_forwardTreating chitin with H2O, -OH hydrolyzes its amide linkages, forming a compound called chitosan. What is the structure of chitosan? Chitosan has been used in shampoos, bers for sutures, and wound dressings.arrow_forward
- 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.arrow_forwardDraw the structure of each peptide. Label the N-terminal and C-terminal amino acids and all amide bonds. a. Val–Glu b. Gly–His–Leu c. M–A–T–Tarrow_forwardThe structure among the following that represents an amide (peptide) bond is: N H N-H -C-O- -C-O-H A B он C-0- -C-N- D structure A structure D structure B structure C |arrow_forward
- 22-48 How many amino acid residues in the A chain of insulin are the same in insulin from humans, cattle (bovine), hogs, and sheep?arrow_forward22-42 (a) How many atoms of the peptide bond lie in the same plane? (b) Which atoms are they?arrow_forwardFor the tripeptide GlyAlaCys a. What amino acid is located at the peptides N-terminal end? b. What amino acid is located at the peptides C-terminal end? c. How many peptide bonds are present? d. How many amide linkages are present?arrow_forward
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