Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 21, Problem 66P
Synthesize (Z)-hept-5-en-2-one from ethyl acetoacetate
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Chapter 21 Solutions
Organic Chemistry (6th Edition)
Ch. 21.2 - Problem 23.1 Draw the enol or keto tautomer(s) of...Ch. 21.2 - Problem 23.3 When phenylacetaldehyde is dissolved...Ch. 21.3 - Prob. 5PCh. 21.3 - Problem 23.5 Which bonds in the following...Ch. 21.3 - Prob. 7PCh. 21.3 - Prob. 8PCh. 21.3 - Prob. 9PCh. 21.4 - Prob. 10PCh. 21.5 - Prob. 11PCh. 21.7 - Problem 23.11 Draw the products of each...
Ch. 21.7 - Problem 23.12 Draw the products of each reaction....Ch. 21.7 - Prob. 14PCh. 21.7 - Prob. 15PCh. 21.8 - Prob. 16PCh. 21.8 - Prob. 17PCh. 21.8 - Prob. 18PCh. 21.8 - Problem 23.18 How can pentan-2-one be converted...Ch. 21.8 - Problem 23.19 Identify A, B, and C, intermediates...Ch. 21.9 - Problem 23.20 Which of the following compounds...Ch. 21.9 - Problem 23.21 Draw the products of each...Ch. 21.9 - Prob. 23PCh. 21.9 - Prob. 24PCh. 21.9 - Prob. 25PCh. 21.10 - Prob. 26PCh. 21.10 - Prob. 27PCh. 21.10 - Prob. 28PCh. 21.10 - Prob. 29PCh. 21 - 23.29 Draw enol tautomer(s) for each compound....Ch. 21 - 22.30 The cis ketone A is isomerized to a trans...Ch. 21 - 23.31 Draw enol tautomer(s) for each compound.
...Ch. 21 - Prob. 33PCh. 21 - Prob. 34PCh. 21 - 23.35 Rank the labeled protons in each compound in...Ch. 21 - Prob. 36PCh. 21 - Prob. 37PCh. 21 - 23.38 Acyclovir is an effective antiviral agent...Ch. 21 - 23.39 Explain why forms two different alkylation...Ch. 21 - Prob. 40PCh. 21 - 23.42 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 42PCh. 21 - Prob. 43PCh. 21 - 23.45 Devise a synthesis of valproic acid , a...Ch. 21 - Prob. 57PCh. 21 - 23.57 Draw a stepwise mechanism showing how two...Ch. 21 - 23.58 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 65PCh. 21 - 23.66 Synthesize (Z)-hept-5-en-2-one from ethyl...
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- CH3 Ph3P-CHCH3 H3C H3C Aldehydes and ketones are converted into alkenes by means of a direct nucleophilic addition called the Wittig reaction. In the reaction, a triphenylphosphorine ylide, also called a phosphorane, adds to an aldehyde/ketone to give a four-membered cyclic intermediate called an oxaphosphetane. The oxaphosphetane is not isolated but instead spontaneously decomposes to release triphenylphosphine oxide and an alkene. Ph3P-CHCH3 H3C The ylide is formed by reaction of triphenylphosphine, a good nucleophile, with a primary alkyl halide in an S 2 reaction, followed by deprotonation of the carbon with a strong base, such as butyllithium. The carbonyl carbon and the carbon originally bonded to the halogen become the two carbons with the double bond in the product alkene :0: CH3 Com The real value of the Wittig reaction lies in its ability to yield an alkene of predictable structure, as the C-C bond is precisely where the C=O bond was in the reactant and no isomers (other than…arrow_forwardWhat is the major product formed when 3-methyl-1-butene is treated with Hg(C2H3O2)2 in a THF/ethanol mixture followed by NaBH4 in base?arrow_forwardDraw the principal organic product for the reaction of 1-bromopentane with lithium in diethyl ether, followed by formaldehyde in diethyl ether, and then followed by dilute acid.arrow_forward
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