Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 23, Problem 23.42P
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Which of the following chemical equations depicts an alkylation reaction?
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C6H12() → C6H10() + H2(g)
CH2ClCH2Cl(g) + H2(g) → CH3CH3(g) + Cl2(g)
CHClCHCl(g) → CH2ClCH2Cl(g)
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Chapter 23 Solutions
Organic Chemistry
Ch. 23 - Problem 23.1 Draw the enol or keto tautomer(s) of...Ch. 23 - Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.3PCh. 23 - Prob. 23.4PCh. 23 - Which CH bonds in the following molecules are...Ch. 23 - Prob. 23.6PCh. 23 - Prob. 23.7PCh. 23 - When ethyl acetoacetate (CH3COCH2CO2CH2CH3) is...Ch. 23 - Prob. 23.9PCh. 23 - Prob. 23.10P
Ch. 23 - Prob. 23.11PCh. 23 - Problem 23.11 Draw the products of each...Ch. 23 - Problem 23.12 Draw the products of each reaction....Ch. 23 - Prob. 23.14PCh. 23 - Prob. 23.15PCh. 23 - Prob. 23.16PCh. 23 - Prob. 23.17PCh. 23 - Prob. 23.18PCh. 23 - Problem 23.18 How can pentan-2-one be converted...Ch. 23 - Problem 23.19 Identify A, B, and C, intermediates...Ch. 23 - Prob. 23.21PCh. 23 - Problem 23.21 Draw the products of each...Ch. 23 - Prob. 23.23PCh. 23 - What alkyl halides are needed to prepare each...Ch. 23 - Prob. 23.25PCh. 23 - Prob. 23.26PCh. 23 - Prob. 23.27PCh. 23 - Prob. 23.28PCh. 23 - Prob. 23.29PCh. 23 - 23.29 Draw enol tautomer(s) for each compound....Ch. 23 - 22.30 The cis ketone A is isomerized to a trans...Ch. 23 - Draw enol tautomers for each compound. a. b. c.Ch. 23 - Prob. 23.33PCh. 23 - What hydrogen atoms in each compound have a pKa25?...Ch. 23 - Rank the labeled protons in each compound in order...Ch. 23 - Prob. 23.36PCh. 23 - Prob. 23.37PCh. 23 - Prob. 23.38PCh. 23 - Prob. 23.39PCh. 23 - 23.38 Acyclovir is an effective antiviral agent...Ch. 23 - Prob. 23.41PCh. 23 - 23.39 Explain why forms two different alkylation...Ch. 23 - 23.41 Acid-catalyzed bromination of pentanone ...Ch. 23 - Draw a stepwise mechanism for each reaction. a. b.Ch. 23 - What alkyl halides are needed to prepare each...Ch. 23 - Use the malonic ester synthesis to prepare each...Ch. 23 - 23.45 Devise a synthesis of valproic acid , a...Ch. 23 - Synthesize each compound from diethyl malonate....Ch. 23 - Prob. 23.49PCh. 23 - What alkyl halides are needed to prepare each...Ch. 23 - Synthesize each compound from ethyl acetoacetate....Ch. 23 - Draw the organic products formed in each reaction....Ch. 23 - 23.51 Draw the products formed (including...Ch. 23 - Prob. 23.54PCh. 23 - 23.54 Clopidogrel is the generic name for Plavix,...Ch. 23 - 23.55 What reaction conditions—base, solvent, and...Ch. 23 - Explain why each of the following reactions will...Ch. 23 - Prob. 23.58PCh. 23 - 23.57 Draw a stepwise mechanism showing how two...Ch. 23 - 23.58 Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.61PCh. 23 - 23.60 Draw stepwise mechanisms illustrating how...Ch. 23 - Prob. 23.63PCh. 23 - Prob. 23.64PCh. 23 - Convert acetophenone (C6H5COCH3) into each of the...Ch. 23 - Prob. 23.66PCh. 23 - Prob. 23.67PCh. 23 - Prob. 23.68PCh. 23 - Synthesize each product from ethyl acetoacetate...Ch. 23 - Prob. 23.70PCh. 23 - Prob. 23.71PCh. 23 - 23.68 Capsaicin, the spicy component of hot...Ch. 23 - 23.69 Treatment of W with , followed by , affords...Ch. 23 - Prob. 23.74PCh. 23 - Prob. 23.75PCh. 23 - Prob. 23.76PCh. 23 - Prob. 23.77PCh. 23 - Prob. 23.78P
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- helparrow_forwarda)Step by step show the reaction of 1 mol of water from the 3,3-dimethyl-2-pentanol compound in acid-catalyzed medium.Name the main product formed. b)Indicate whether the resulting product shows the geometric isomer or not. c)Write the products formed when the product is ozonized and oxidized.arrow_forwardDescribe a sequence of reactions by which cis-2-pentene could be prepared from acetylene.arrow_forward
- Draw the structure of the organic product formed when the given compounds undergo the three-step reaction sequence indicated. Select Draw Rings More Erase C Br 1. NaOC,H5. C,H5OH 2. NaOH, H2O 3. H3O*, heatarrow_forwardA) An Alcohol X has the structure of (CH,), C(OH)CH(CH,),. i) State the IUPAC name of alcohol X. i) Outline the mechanism for the reaction occurring when alcohol X is converted into 2,3-dimethylbut-2-ene in the presence of a strong acid. i) Name the reaction in part ii). iv) Draw the structure and state the IUPAC name of an isomer of 2,3-dimethyl-2- butene which is also formed in the reaction. v) Explain why two products are obtained. vi) Write an equation for the reaction between alcohol X and ethanoyl chloride. vii) Outline a mechanism for this reaction, using ROH to represent the alcohol in the mechanism.arrow_forwardWhat is the slow, rate-determining step, in the acid-catalyzed dehydration of 2- butanol? Loss of a b-hydrogen from the carbocation to form an alkene. Protonation of the alcohol to form an oxonium ion. Loss of water from the oxonium ion to form a carbocation. The simultaneous loss of a B-hydrogen and water from the oxonium ion.arrow_forward
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- Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardAldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule of alcohol gives an acetal and a molecule of water. We study this reaction in Chapter 16. Draw structural formulas for the hemiacetal and acetal formed from these reagents. The stoichiometry of each reaction is given in the problem.arrow_forwardWrite in the correct reagents for these transformations: a) cyclohexanol -→ chlorocyclohexane b) 2-butanone 2-butanol ward 2-butanol 2-butanone toluene - → benzoic acid nitrobenzene → anilinearrow_forward
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