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ORGANIC CHEMISTRY (LOOSELEAF)
6th Edition
ISBN: 9781260475630
Author: SMITH
Publisher: MCG
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Chapter 27, Problem 68P
Interpretation Introduction
Interpretation: A stepwise synthesis of the tripeptide Val-Leu-Val from
Concept introduction: Amino acids are biologically important organic molecules that contain
When two or more amino acids are linked in a chain, a compound called peptide is formed in which the carboxyl group of each acid is joined to the amino group of the next forming a
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Devise a synthesis of CH3CH2C≡CCH2CH2CH3 using CH3CH2CH=CH2 as the starting material. You may use any other organic compounds or inorganic reagents.
Devise a synthesis of CH3CH2C ≡ CCH2CH2OH from CH3CH2OH as the only organic starting material. You may use any other needed reagents.
Devise a stepwise synthesis of the tripeptide Val–Leu–Val from 3-methylbutanal [(CH3)2CHCH2CHO] as the only organic starting material. You may also use any required inorganic or organic reagents.
Chapter 27 Solutions
ORGANIC CHEMISTRY (LOOSELEAF)
Ch. 27.1 - Prob. 1PCh. 27.1 - Problem 29.2
What form exists at the isoelectric...Ch. 27.1 - Problem 29.3
Explain why the of the group of an...Ch. 27.1 - Prob. 4PCh. 27.2 - Problem 29.5
What -halo carbonyl compound is...Ch. 27.2 - Problem 29.6
The enolate derived from diethyl...Ch. 27.2 - Problem 29.7
What amino acid is formed when is...Ch. 27.2 - Problem 29.8
What aldehyde is needed to synthesize...Ch. 27.2 - Problem 29.9
Draw the products of each...Ch. 27.3 - Prob. 10P
Ch. 27.3 - Prob. 11PCh. 27.3 - Prob. 12PCh. 27.4 - Problem 29.13
What alkene is needed to synthesize...Ch. 27.5 - Problem 29.14
Draw the structure of each peptide....Ch. 27.5 - Problem 29.15
Name each peptide using both the...Ch. 27 - Draw the product formed when the following amino...Ch. 27 - With reference to the following peptide: a...Ch. 27 - Prob. 31PCh. 27 - Histidine is classified as a basic amino acid...Ch. 27 - Tryptophan is not classified as a basic amino acid...Ch. 27 - What is the structure of each amino acid at its...Ch. 27 - What is the predominant form of each of the...Ch. 27 - 29.37 What is the predominant form of each of the...Ch. 27 - a. Draw the structure of the tripeptide A–A–A, and...Ch. 27 - 29.39 Draw the organic products formed in each...Ch. 27 - 29.40 What alkyl halide is needed to synthesize...Ch. 27 - Prob. 50PCh. 27 - Draw the structure for each peptide: (a) Phe–Ala;...Ch. 27 - 29.52 For the tetrapeptide Asp–Arg–Val–Tyr:
a....Ch. 27 - Prob. 53PCh. 27 - Prob. 54PCh. 27 - 29.55 Draw the amino acids and peptide fragments...Ch. 27 - Prob. 56PCh. 27 - Prob. 57PCh. 27 - Prob. 58PCh. 27 - 29.59 An octapeptide contains the following amino...Ch. 27 - 29.60 Draw the organic products formed in each...Ch. 27 - 29.65 Draw the mechanism for the reaction that...Ch. 27 - 29.66 Which of the following amino acids are...Ch. 27 - 29.67 After the peptide chain of collagen has been...Ch. 27 - Prob. 68PCh. 27 - Prob. 69PCh. 27 - 29.70 The anti-obesity drug orlistat works by...Ch. 27 - Prob. 71P
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- Name the structure. Heating compound A in the presence of H2SO4 results in which product?arrow_forwardDevise a synthesis of each compound from CH3CH2OH as the only organic starting material; that is, every carbon in the product must come from a molecule of ethanol. You may use any other needed inorganic reagents.arrow_forwardSynthesize the product from the given material. Give the reagents necessary and draw out any intermediate products along the way.arrow_forward
- Determine the reagents and the structure of the intermediate products to complete the following reaction sequence (1/2 eq.) NaNH, Br OH OHarrow_forwardDevise a synthesis of each compound using CH3CH2CH=CH2 as the starting material. You may use any other organic compounds or inorganic reagents.arrow_forwarda) b) c) d) type type OEt type SN ₂ HI ether Br₂, H₂O alkere in a) NaOEt/EtOH b) neutralize type elimination Ixp a) cH₂ B‹ b) NaOH you c) aq. malonic Ester Synthesis aq, HCl OHarrow_forward
- Devise a synthesis of CH3CH2C≡CCH2CH2CH3using CH3CH2CH=CH2as the starting material. You may use any other organic compounds or inorganic reagents.arrow_forwardThe reaction of p-cresol with CH2=O resembles the reaction of phenol (PhOH) with CH2=O, except that the resulting polymer is thermoplastic but not thermosetting. Draw the structure of the polymer formed, and explain why the properties of these two polymers are so different.arrow_forwardWhat product is formed when attached compound is treated with either Ag2O, NH4OH or Na2Cr2O7, H2SO4, H2O?arrow_forward
- could you synthesize isopropyl propyl ether, using isopropyl alcohol as the only carbon-containing reagent?arrow_forwardDraw the product formed when CH3CH2C=CH is treated with each of the following sets of reagents: (a) H2O, H2SO4, HgSO4; and (b) R2BH, followed by H2O2, HO−.arrow_forwardThe following reaction could be classified as which type of acyl substitution? More than one step might be nucleophilic needed. O || CH3CH₂CHCH₂C-Cl CH3 Select one or more: reduction. hydrolysis. alcoholysis. amoniolysis Grignard reaction. + O || CH₂CH₂CHCH₂C-OH CH;arrow_forward
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