OWL V2 with MindTap Reader and Student Solutions Manual eBook for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
8th Edition
ISBN: 9781305865617
Author: Brown, Iverson, Anslyn, FOOTE
Publisher: Cengage Learning US
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Chapter 23, Problem 23.53P
Propose a synthesis for the systemic agricultural fungicide tridemorph from dodecanoic acid (lauric acid), propene, and a one-carbon building block. How many stereoisomers are possible for tridemorph?
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1. The ketone 2-heptanone has been identified as contributing to the odor of a number of dairy products, including condensed milk and cheddar cheese. Describe the synthesis of 2-heptanone from acetylene and any necessary organic and inorganic reagents.
2. Compound A has the molecular formula C14H25Br and was obtained by reaction of sodium acetylide (HC≡CNa) )with 1,12-dibromododecane. On treatment of compound A with sodium amide, it was converted to compound B (C14H24). Ozonolysis of compound B gave the diacid HO2C(CH2)12CO2H. Catalytic hydrogenation of compound B over Lindlar palladium gave compound C (C14H26), while hydrogenation over platinum gave compound D (C14H28). Sodium-ammonia reduction of compound B gave compound E (C14H26). Both C and E yielded O═CH(CH2)12CH═O on ozonolysis. Assign structures to compound A through E so as to be consistent with the observed transformations.
Propose a synthesis for the systemic agricultural fungicide tridemorph from dodecanoic
acid (lauric acid), propene, and a one-carbon building block. How many stereoisomers
are possible for tridemorph?
CH3
→CH3(CH2)10COOH + CH3CH=CH,
H3C
(CH2) 12CH3
Tridemorph
Dodecanoic acid
Propene
(Lauric acid)
A 2-bromobutane react with methanol and form a enantiomeric pair of 2-methoxybutane. Draw the structures of the enntiomeric pairs of ethers.
Chapter 23 Solutions
OWL V2 with MindTap Reader and Student Solutions Manual eBook for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
Ch. 23.1 - Prob. 23.1PCh. 23.2 - Prob. 23.2PCh. 23.2 - Prob. 23.3PCh. 23.2 - Prob. 23.4PCh. 23.5 - Prob. 23.5PCh. 23.5 - Prob. AQCh. 23.5 - What is the hybridization of the nitrogen in...Ch. 23.5 - Prob. CQCh. 23.5 - The pKas of the conjugate acids of aniline and...Ch. 23.5 - Prob. EQ
Ch. 23.5 - Prob. FQCh. 23.5 - Prob. GQCh. 23.5 - Select the stronger acid from each pair of...Ch. 23.6 - Prob. 23.7PCh. 23.6 - Prob. 23.8PCh. 23.6 - Prob. 23.9PCh. 23.7 - Prob. 23.10PCh. 23.8 - Prob. 23.11PCh. 23.8 - Prob. 23.12PCh. 23.8 - Prob. 23.13PCh. 23.9 - Prob. 23.14PCh. 23.10 - In Example 23.15, you considered the product of...Ch. 23 - Prob. 23.16PCh. 23 - Prob. 23.17PCh. 23 - Prob. 23.18PCh. 23 - Prob. 23.19PCh. 23 - Prob. 23.20PCh. 23 - Prob. 23.21PCh. 23 - Prob. 23.22PCh. 23 - Account for the formation of the base peaks in...Ch. 23 - Prob. 23.24PCh. 23 - Select the stronger base from each pair of...Ch. 23 - The pKa, of the conjugate acid of morpholine is...Ch. 23 - Which of the two nitrogens in pyridoxamine (a form...Ch. 23 - Prob. 23.28PCh. 23 - Prob. 23.29PCh. 23 - Prob. 23.30PCh. 23 - Prob. 23.31PCh. 23 - Suppose you have a mixture of these three...Ch. 23 - Prob. 23.33PCh. 23 - Prob. 23.34PCh. 23 - Prob. 23.35PCh. 23 - Prob. 23.36PCh. 23 - Prob. 23.37PCh. 23 - (S)-Glutamic acid is one of the 20 amino acid...Ch. 23 - Prob. 23.39PCh. 23 - Propose a structural formula for the compound...Ch. 23 - Prob. 23.41PCh. 23 - The pyrolysis of acetic esters to give an alkene...Ch. 23 - Propose steps for the following conversions using...Ch. 23 - Show how to bring about each step in this...Ch. 23 - Show how to bring about each step in the following...Ch. 23 - Prob. 23.48PCh. 23 - Prob. 23.49PCh. 23 - Methylparaben is used as a preservative in foods,...Ch. 23 - Prob. 23.51PCh. 23 - Prob. 23.52PCh. 23 - Propose a synthesis for the systemic agricultural...Ch. 23 - Prob. 23.54PCh. 23 - Several diamines are building blocks for the...Ch. 23 - Prob. 23.56PCh. 23 - Prob. 23.57PCh. 23 - Prob. 23.58PCh. 23 - Prob. 23.59PCh. 23 - Following is a retrosynthesis for the coronary...Ch. 23 - Prob. 23.61PCh. 23 - Prob. 23.62PCh. 23 - Given this retrosynthetic analysis, propose a...Ch. 23 - Prob. 23.64PCh. 23 - Following is a series of anorexics (appetite...Ch. 23 - Prob. 23.66PCh. 23 - Prob. 23.67PCh. 23 - Show how the synthetic scheme developed in Problem...Ch. 23 - Prob. 23.69PCh. 23 - Prob. 23.70PCh. 23 - Prob. 23.71PCh. 23 - Prob. 23.72P
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