Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
5th Edition
ISBN: 9781260170405
Author: SMITH
Publisher: MCG
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Chapter 22, Problem 22.55P
When acetic acid (
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Exercice 5 Complete the following reactions, giving details of the reaction mechanisms Exercice 6 Give
the compound A formed in the following reaction → NaOH
Can you draw the mechanism for the synthesis of cyclohexene from cyclohexanol through an acid-catalyzed dehydration reaction. Where
Phosphoric acid donates a proton ((H^+)) to the hydroxyl group of cyclohexanol, forming a protonated cyclohexanol intermediate. • The protonated cyclohexanol undergoes dehydration, leading to the removal of a water molecule and the formation of cyclohexene. • The released proton combines with water to form hydronium ion (H3O+), regenerating the catalyst.
The mechanism should illustrate the acid-catalyzed dehydration process, where phosphoric acid facilitates the removal of water from cyclohexanol, resulting in the formation of cyclohexene.
Ketones and aldehydes react with sodium acetylide (the sodium salt of acetylene) to give alcohols, as shown in the following example:
R1
ОН
1. НС—с: Na*
R2
R1
R2
2. Нзо"
HC
Draw the structure of the major reaction product when the following compound reacts with sodium acetylide, assuming that the reaction takes
preferentially from the Si face of the carbonyl group.
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
• You do not have to explicitly draw H atoms.
• If a group is achiral, do not use wedged or hashed bonds on it.
CH3
CH
Chapter 22 Solutions
Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
Ch. 22 - Prob. 22.1PCh. 22 - Draw the three possible resonance structures for...Ch. 22 - Prob. 22.3PCh. 22 - Give an IUPAC or common name for each compound. a....Ch. 22 - Problem 22.5 Draw the structure corresponding to...Ch. 22 - Problem 22.6 Explain why the boiling point of is...Ch. 22 - Problem 22.7 How would the compounds in each pair...Ch. 22 - Problem 22.8 Deduce the structures of compounds ...Ch. 22 - Problem 22.9 Without reading ahead in Chapter 22,...Ch. 22 - Rank the compounds in each group in order of...
Ch. 22 - Prob. 22.11PCh. 22 - Prob. 22.12PCh. 22 - Prob. 22.13PCh. 22 - Prob. 22.14PCh. 22 - Problem 22.15 Draw the products of each...Ch. 22 - Problem 22.16 Draw the products of each reaction.
...Ch. 22 - Prob. 22.17PCh. 22 - Problem 22.18 Draw a stepwise mechanism for the...Ch. 22 - Prob. 22.19PCh. 22 - Problem 22.20 Fenofibrate is a...Ch. 22 - Problem 22.21 What product is formed when the...Ch. 22 - How would you synthesize olestra from sucrose?
Ch. 22 - Problem 22.23 What is the composition of the soap...Ch. 22 - Problem 22.24 Draw a stepwise mechanism for the...Ch. 22 - Prob. 22.25PCh. 22 - Problem 22.26 Some penicillins cannot be...Ch. 22 - Prob. 22.27PCh. 22 - Prob. 22.28PCh. 22 - Prob. 22.29PCh. 22 - Problem 22.30 Glucosamine is a dietry supplement...Ch. 22 - Draw the products of each reaction. a. c. b.Ch. 22 - Draw a tautomer of each compound.
a. b. c.
Ch. 22 - Draw the product of each reaction. a. b.Ch. 22 - Draw the product of each reaction. a. b.Ch. 22 - Prob. 22.35PCh. 22 - Problem 22.36 Outline two different ways that can...Ch. 22 - 22.37 Rank the following compounds in order of...Ch. 22 - Prob. 22.38PCh. 22 - Prob. 22.39PCh. 22 - 22.40 Give the IUPAC or common name for each...Ch. 22 - 22.41 Give the structure corresponding to each...Ch. 22 - Prob. 22.42PCh. 22 - 22.43 Explain why is a stronger acid and a weaker...Ch. 22 - (a) Propose an explanation for the difference in...Ch. 22 - Draw the product formed when phenylacetic acid is...Ch. 22 - Draw the product formed when phenylacetonitrile ...Ch. 22 - 22.47 Draw the organic products formed in each...Ch. 22 - Prob. 22.48PCh. 22 - Prob. 22.49PCh. 22 - Prob. 22.50PCh. 22 - Prob. 22.51PCh. 22 - Prob. 22.52PCh. 22 - Prob. 22.53PCh. 22 - 22.54 Draw a stepwise mechanism f or the following...Ch. 22 - 22.55 When acetic acid () is treated with a trace...Ch. 22 - Prob. 22.56PCh. 22 - Prob. 22.57PCh. 22 - Draw a stepwise mechanism for the following...Ch. 22 - Prob. 22.59PCh. 22 - Prob. 22.60PCh. 22 - Prob. 22.61PCh. 22 - Draw a stepwise mechanism for the following...Ch. 22 - 22.63 Acid-catalyzed hydrolysis of forms compound...Ch. 22 - 22.64 What carboxylic acid and alcohol are needed...Ch. 22 - Problem 22.65 Devise a synthesis of each compound...Ch. 22 - Prob. 22.66PCh. 22 - Prob. 22.67PCh. 22 - Prob. 22.68PCh. 22 - Prob. 22.69PCh. 22 - 22.70 What polyester or poly amide can be prepared...Ch. 22 - 22.71 What two monomers are needed to prepare each...Ch. 22 - Prob. 22.72PCh. 22 - 22.73 How can IR spectroscopy be used to...Ch. 22 - 22.74 Rank the following compounds in order of...Ch. 22 - 22.75 Identify the structures of each compound...Ch. 22 - 22.76 Identify the structures of A and B, isomers...Ch. 22 - Prob. 22.77PCh. 22 - 22.78 Identify the structure of compound C...Ch. 22 - 22.79 Identify the structures of D and E, isomers...Ch. 22 - 22.80 With reference to amides A and B, the...Ch. 22 - Prob. 22.81PCh. 22 - Prob. 22.82PCh. 22 - Prob. 22.83PCh. 22 - Draw a stepwise mechanism for the following...Ch. 22 - Draw a stepwise mechanism for the following...
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- The following pKa values have been measured. Explain why a hydroxyl group in the para position decreases the acidity while a hydroxyl group in the meta position increases the acidity.arrow_forwardComplete each acid-base reaction and predict whether the position of equilibrium lies toward the left or toward the right. (a) CH3CCH+CH3CH2ONa+CH3CH3OH (b) CH3CCCH2CH2OH+Na+NH2NH3(l)arrow_forwardH3C OH OH H+ CH3 Esters can be synthesized by an acid-catalyzed nucleophilic acyl substitution between an alcohol and a carboxylic acid; this process is called the Fischer esterification reaction. Because the alcohol oxygen is a poor nucleophile, the carbonyl carbon is made a better electrophile by protonation of the carbonyl oxygen. The steps of the synthesis are all reversible. The reaction is generally driven to completion by using an excess of the liquid alcohol as a solvent, or by distilling off the product as it forms. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CIX 10-4 H₂O CH3 H₂O CH3arrow_forward
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- b) The Wolf-Kishner reduction is a reaction used in Organic Chemistry to convert carbonyl functionalities into methylene group. The reaction was used to convert an aldehyde or ketone to an alkane using hydrazine, base and thermal conditions. The mechanism begins with the attack of hydrazine of the aldehyde or ketone. Stage 1: The reaction of aldehyde/ketone with hydrazine to produce hydrazine Stage 2: Reaction with the base and heat to convert hydrozone to alkane Write the mechanism of the reaction.arrow_forwardThe behavior of esters and ketones in a reaction with a nucleophile is different because: 1) the carbonyl of the ketone is more positive. 2) the ester cannot form a tetrahedral intermediate. 3) the two oxygens of the ester sterically hinder the nucleophile attack. 4) there is a reasonable leaving group in the ester. O 2 O 4 O 1arrow_forwardThis question is about the reaction scheme shown. CH₂ CH₂ step 2 step 1 NO₂ NH₂ NHCOCK, Amine A CH₂CI step 4 step 5 Amine B State the reagents needed for step 1 and the reagents needed for step 2. step 1 step 2 Give the name of the mechanism for the reaction in step 3. CH₂ CHÍNH, step 3arrow_forward
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