Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 22, Problem 22.58P
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
Organic Chemistry-Package(Custom)
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.Ch. 22 - Problem 22.5 Draw the structure corresponding to...Ch. 22 - Prob. 22.6PCh. 22 - How would the compounds in each pair differ in...Ch. 22 - Problem 22.8 Deduce the structures of compounds ...Ch. 22 - Prob. 22.9PCh. 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 - What is the composition of the soap prepared by...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.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 - Prob. 22.40PCh. 22 - Give thestructure corresponding to each name. a....Ch. 22 - Prob. 22.42PCh. 22 - Prob. 22.43PCh. 22 - 22.43 Explain why is a stronger acid and a weaker...Ch. 22 - Draw the product formed when pentanoyl chloride...Ch. 22 - Draw the product formed when pentanoic anhydride...Ch. 22 - Draw the product formed when phenylacetic acid is...Ch. 22 - Prob. 22.48PCh. 22 - Prob. 22.49PCh. 22 - Draw the product formed when phenylacetonitrile ...Ch. 22 - Prob. 22.51PCh. 22 - Prob. 22.52PCh. 22 - Prob. 22.53PCh. 22 - Prob. 22.54PCh. 22 - Prob. 22.55PCh. 22 - Prob. 22.56PCh. 22 - Draw a stepwise mechanism for each reaction. a. b.Ch. 22 - When acetic acid CH3COOH is treated with a trace...Ch. 22 - Prob. 22.59PCh. 22 - Prob. 22.60PCh. 22 - Prob. 22.61PCh. 22 - Prob. 22.62PCh. 22 - Prob. 22.63PCh. 22 - Draw a stepwise mechanism for the following...Ch. 22 - 22.63 Acid-catalyzed hydrolysis of forms compound...Ch. 22 - Prob. 22.66PCh. 22 - Devise a synthesis of each compound using...Ch. 22 - Convert 1-bromohexane (CH3CH2CH2CH2CH2CH2Br) into...Ch. 22 - Prob. 22.69PCh. 22 - Prob. 22.70PCh. 22 - Prob. 22.71PCh. 22 - Prob. 22.72PCh. 22 - Prob. 22.73PCh. 22 - Prob. 22.74PCh. 22 - Devise a synthesis of each labeled compound using...Ch. 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. 22.78PCh. 22 - How can IR spectroscopy be used to distinguish...Ch. 22 - Rank the compounds in each group 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. 22.83PCh. 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. 22.87PCh. 22 - Prob. 22.88PCh. 22 - Prob. 22.89PCh. 22 - Draw a stepwise mechanism for the following...Ch. 22 - Draw a stepwise mechanism for the following...
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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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