ORGANIC CHEMISTRY
6th Edition
ISBN: 9781260826791
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 27.2, Problem 6P
The enolate derived from diethyl acetamidomalonate is treated with each of the following
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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.
Write the products of the following acid-base reactions:
(a) CH3OH + H2SO4 ² ?
(b) CH3OH + NANH2 2 ?
(c) CH3NH3+ Cl- + NaOH ?
The following chemical reaction is used to synthesize a flavouring agent that has an aroma similar to bananas.
H₂SO4(aq)
CH3COOH(1) + CH₂(CH₂)₂OH(1)
I
||
Identify the type of reaction that is represented by this synthesis.
Select one:
O hydrogenation
O esterification
O addition
O substitution
O elimination
Identify the functional group and the IUPAC name for each of the three compounds in the reaction below:
H₂SO4(aq)
I
Compound Functional Group IUPAC Name
II
CH₂COOH(1) + CH₂(CH₂)₂OH(1)
I
||
III
CH3COO(CH₂)₂CH₂(1) + H₂O(1)
III
IV
◆
→
◆
CH3COO(CH₂)₂CH₂(1) + H₂O(1)
IV
|||
◆
◆
Chapter 27 Solutions
ORGANIC CHEMISTRY
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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- The oxidation of 3-methylbutanal with potassium permanganate in an acid medium produces compound A and the reduction of cyclohexanone with NaBH4 produces compound B. Indicate the CORRECT alternative: a) A reacts rapidly with water to produce a carboxylic acid. b) Reaction of B with methylamine produces an amide. c) Reaction of A with an acyl chloride produces an ester. d) B reacts with HCN to produce a cyanohydrin. e) The reaction of A and B in an acid medium produces cyclohexyl 3-methylbutanoate.arrow_forwardDraw the structure of a compound of molecular formula C 9H 11NO that contains a benzene ring and a: (a) 1 ° amide; (b) 2 ° amide; (c) 3 ° amide.arrow_forward(a) Draw the structures for the eight constitutional isomers of molecular formula C 4H 11N. (b) Give the systematic name for each amine. (c) Identify the chirality center present in one of the amines.arrow_forward
- When the ester ethyl butanoate, CH3CH2CH2COOCH,CH3, is hydrolyzed under acidic conditions, which compounds are the products? O cthyl alcohol and the butanoate ion O ethyl alcohol and butanoic cid O butanol and cthanoic (acctic acid) O butanol and the cthanoate ionarrow_forwardTrimyristin is obtained from coconut oil and has the molecular formula C45H86O6. On being heated with aqueous sodium hydroxide followed by acidification, trimyristin was converted to glycerol and tetradecanoic acid as the only products. What is the structure of trimyristin?arrow_forward(i) Draw the structural formula of compounds L, M, N and P (ii) Name the type of chemical reaction for the formation of compound N.arrow_forward
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