Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 20, Problem 20.11P
Draw the structure of both an acid chloride and an ester that can be used to prepare each compound by reduction.
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When reacting an acid halide with amines, it is necessary to use at least two moles of the amine because:
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B) Using one mole of the amine leads to a neutralization reaction between the two reactants
C) Excess amine is needed to react with the hydrohalic acid produced
D) The second mole of amine is needed for deprotonation.
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Phenols are aromatic rings with an alcohol functional group attached directly to the ring. These compounds have unique acidity and solubility for alcohol groups. Predict the solubility of this phenol in water.
Chapter 20 Solutions
Organic Chemistry-Package(Custom)
Ch. 20 - Prob. 20.1PCh. 20 - Which carbonyl groups in the anticancer drug taxol...Ch. 20 - Prob. 20.3PCh. 20 - Prob. 20.4PCh. 20 - Problem 20.5 What aldehyde or ketone is needed to...Ch. 20 - Prob. 20.6PCh. 20 - Problem 20.7 Draw the products formed when is...Ch. 20 - Prob. 20.8PCh. 20 - Prob. 20.9PCh. 20 - Prob. 20.10P
Ch. 20 - Draw the structure of both an acid chloride and an...Ch. 20 - Problem 20.12 Draw the products formed from ...Ch. 20 - Prob. 20.13PCh. 20 - Prob. 20.14PCh. 20 - What product is formed when...Ch. 20 - Prob. 20.16PCh. 20 - Problem-20.16 Review the oxidation reactions using...Ch. 20 - Problem-20.17 Write the step(s) needed to convert ...Ch. 20 - Problem-20.18 Oct-1-yne reacts rapidly with ,...Ch. 20 - Draw the product formed when each organometallic...Ch. 20 - Draw the product of each reaction. a.c. b.d.Ch. 20 - Draw the products including stereochemistry of the...Ch. 20 - What Grignard reagent and carbonyl compound are...Ch. 20 - Problem 20.24 Linalool (the Chapter 9 opening...Ch. 20 - Problem 20.25 What Grignard reagent and carbonyl...Ch. 20 - Prob. 20.26PCh. 20 - Draw the products formed when each compound is...Ch. 20 - What ester and Grignard reagent are needed to...Ch. 20 - What organocuprate reagent is needed to convert...Ch. 20 - What reagent is needed to convert (CH3)2CHCH2CHO...Ch. 20 - Prob. 20.31PCh. 20 - What carboxylic acid formed from each alkyl halide...Ch. 20 - Prob. 20.33PCh. 20 - Prob. 20.34PCh. 20 - Problem 20.35 Synthesize each compound from...Ch. 20 - Prob. 20.36PCh. 20 - 20.37 Devise a synthesis of each alcohol from...Ch. 20 - 20.38 Draw the products formed when pentanal is...Ch. 20 - Prob. 20.39PCh. 20 - Draw the product formed when CH3CH2CH2MgBr is...Ch. 20 - Draw the product formed when (CH3CH2CH2CH2)2CuLi...Ch. 20 - The stereochemistry of the products of reduction...Ch. 20 - Prob. 20.43PCh. 20 - What reagent is needed to convert...Ch. 20 - What reagent is needed to convert...Ch. 20 - Draw the products or each reduction reaction. a....Ch. 20 - Prob. 20.47PCh. 20 - Draw all stereoisomers formed in each reaction. a....Ch. 20 - Prob. 20.49PCh. 20 - 20.46 Treatment of ketone A with ethynylithium...Ch. 20 - 20.47 Explain why metal hydride reduction gives an...Ch. 20 - Prob. 20.52PCh. 20 - 20.49 Identify the lettered compounds in the...Ch. 20 - Prob. 20.54PCh. 20 - Draw a stepwise mechanism for each reaction. a. b.Ch. 20 - Prob. 20.56PCh. 20 - 20.54 Draw a stepwise mechanism for the following...Ch. 20 - What Grignard reagent and aldehyde or ketone are...Ch. 20 - Prob. 20.59PCh. 20 - What ester and Grignard reagent are needed to...Ch. 20 - What organolithium reagent and carbonyl compound...Ch. 20 - 20.59 What epoxide and organometallic reagent are...Ch. 20 - Prob. 20.63PCh. 20 - 20.61 Propose two different methods to synthesize...Ch. 20 - Synthesize each compound from cyclohexanol using...Ch. 20 - Prob. 20.66PCh. 20 - Prob. 20.67PCh. 20 - Devise three different methods to prepare each...Ch. 20 - Convert benzene into each compound. You may also...Ch. 20 - Design a synthesis of each compound from alcohols...Ch. 20 - Synthesize each compound from the given starting...Ch. 20 - 20.69 An unknown compound A (molecular formula )...Ch. 20 - 20.70 Treatment of compound C (molecular formula )...Ch. 20 - 20.71 Treatment of compound E (molecular formula )...Ch. 20 - 20.72 Reaction of butanenitrile () with methyl...Ch. 20 - 20.73 Treatment of isobutene with forms a...Ch. 20 - Prob. 20.77PCh. 20 - Prob. 20.78PCh. 20 - 20.76 Lithium tri-sec-butylborohydride, also known...Ch. 20 - Prob. 20.80PCh. 20 - Prob. 20.81PCh. 20 - Prob. 20.82PCh. 20 - 20.80 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.84P
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- Which three carboxylic acids have salts that are used extensively as food preservatives?arrow_forwardList the following compounds in order of increasing water solubility: a.ethoxyethane b.propanoic acid c.pentane d.1 butanolarrow_forwardDraw structural formulas for the following entities. a. Propanoate ion b. Sodium propanoate c. Acetate ion d. Sodium acetatearrow_forward
- Ester compounds often have a sweet, pleasant odor. Many characteristic fruit scents are largely due to the natural presence of one or more ester compounds. As such, artificial scents for foods are often composed of complex mixtures of various esters. The exact identity and ratio of ingredients that compose a particular scent are closely guarded secrets in the food and fragrance industry. Suppose that you are a chemist working for a company that i creating a new line of air fresheners. The company is considering three scents: apple, pear, and pineapple. The project manager has asked you to prepare the ester compounds that are largely responsible for these scents. The structural formulas for these ester compounds are shown here: Alcohols for Air Freshener Project Molar mass Density Cost, per (g/mL) Reagent (g/mol) 1.00 L methanol 32.04 0.79 $46.20 ethanol 46.07 0.79 $112.00 1-propanol 60.10 0.80 $72.70 1-butanol 74.12 0.81 $72.60 Use the structural formulas of the alcohols and…arrow_forwardGive an acceptable name for these compounds.arrow_forward1) To identify which contains more acid vinegar or lemon juice neutralization with sodium hydroxide can be used. Explain how. 2) The long filaments making up the thread of woven synthetic fabrics are likely polyesters. Describe the special characteristic that the alcohol and carboxylic acid must have so that they can react with each other to produce such long filaments.arrow_forward
- Polyphenols are compounds found in many fruits, vegetables, tea, and wine. Predict the solubility of this polyphenol, gallic acid, in water.arrow_forwardDefine about Reduction of Acid Chlorides and Esters ?arrow_forwardwhy n-hexanol has higher boiling point than n-hexane. why acetic acid is more acidic then butanoic acid. why sugar is soluble in water in terms of their molecular interactions.arrow_forward
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