Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 21, Problem 21.2P
Interpretation Introduction
Interpretation: An explanation for the less reactivity of benzaldehyde than cyclohexanecarbaldehyde towards nucleophilic attack is to be stated.
Concept introduction: Both
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Why aldehydes and ketones do not undergo nucleophilic substitution reaction?
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Chapter 21 Solutions
Organic Chemistry
Ch. 21 - Rank the following compounds in order of...Ch. 21 - Prob. 21.2PCh. 21 - Give the IUPAC name for each aldehyde.Ch. 21 - Prob. 21.4PCh. 21 - Give the IUPAC name for each ketone.Ch. 21 - Prob. 21.6PCh. 21 - Prob. 21.7PCh. 21 - The boiling point of is significantly higher than...Ch. 21 - Which carbonyl group in each pair absorbs at a...Ch. 21 - Problem 21.10 Draw the structure of all...
Ch. 21 - Prob. 21.11PCh. 21 - Prob. 21.12PCh. 21 - Prob. 21.13PCh. 21 - Prob. 21.14PCh. 21 - Problem 21.15 Draw the product of each...Ch. 21 - Prob. 21.16PCh. 21 - Prob. 21.17PCh. 21 - Outline a synthesis of each Wittig reagent from...Ch. 21 - Draw the products including stereoisomers formed...Ch. 21 - Prob. 21.20PCh. 21 - Prob. 21.21PCh. 21 - Show two methods to synthesize each alkene: a...Ch. 21 - Problem 21.22 The product formed when reacts with...Ch. 21 - What 1 amine and carbonyl compound are needed to...Ch. 21 - Prob. 21.25PCh. 21 - Prob. 21.26PCh. 21 - Prob. 21.27PCh. 21 - Problem 21.28 Draw a stepwise mechanism for the...Ch. 21 - Problem 21.29 Draw the products of each...Ch. 21 - Problem 21.30 Label each compound as an acetal, a...Ch. 21 - Problem 21.31 Draw a stepwise mechanism for the...Ch. 21 - Problem 21.32 Draw the products of each...Ch. 21 - Problem 21.33 Safrole is a naturally occurring...Ch. 21 - Problem 21.35 How would you use a protecting group...Ch. 21 - Prob. 21.35PCh. 21 - Problem 21.37 Two naturally occurring compounds...Ch. 21 - Problem 21.38 Draw the products of each...Ch. 21 - Prob. 21.38PCh. 21 - Problem 21.40 (a) Give the IUPAC name for A and B....Ch. 21 - 21.41 Rank the following compounds in order of...Ch. 21 - Prob. 21.41PCh. 21 - Give the IUPAC name for each compound. a. d. g. b....Ch. 21 - Give the structure corresponding to each name. a....Ch. 21 - Including stereoisomers, draw the 11 aldehydes...Ch. 21 - Prob. 21.45PCh. 21 - Prob. 21.46PCh. 21 - What alkyl halide is needed to prepare each Wittig...Ch. 21 - 21.46 Draw the products of each reaction.
a. e....Ch. 21 - Prob. 21.49PCh. 21 - Prob. 21.50PCh. 21 - Prob. 21.51PCh. 21 - Prob. 21.52PCh. 21 - Prob. 21.53PCh. 21 - Rank the following compounds in order of...Ch. 21 - Which compound forms the higher concentration of...Ch. 21 - Prob. 21.56PCh. 21 - What Wittig reagent and carbonyl compound are...Ch. 21 - Prob. 21.58PCh. 21 - What reagents are needed to convert each compound...Ch. 21 - What reagents are needed to convert each compound...Ch. 21 - Prob. 21.61PCh. 21 - Devise a synthesis of each alkene using a Wittig...Ch. 21 - Devise a synthesis of each compound from...Ch. 21 - Prob. 21.64PCh. 21 - Prob. 21.65PCh. 21 - Prob. 21.66PCh. 21 - Prob. 21.67PCh. 21 - Prob. 21.68PCh. 21 - Prob. 21.69PCh. 21 - 21.64 Draw a stepwise mechanism for the following...Ch. 21 - 21.65 Draw a stepwise mechanism f or the following...Ch. 21 - Prob. 21.72PCh. 21 - 21.67 Draw a stepwise mechanism for each...Ch. 21 - 21.68 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 21.75PCh. 21 - Prob. 21.76PCh. 21 - Prob. 21.77PCh. 21 - Prob. 21.78PCh. 21 - Prob. 21.79PCh. 21 - 21.73 Although the carbonyl absorption of cyclic...Ch. 21 - 21.74 Use the and data to determine the...Ch. 21 - 21.75 A solution of acetone in ethanol in the...Ch. 21 - Compounds A and B have molecular formula ....Ch. 21 - 21.77 An unknown compound C of molecular formula ...Ch. 21 - 21.78 An unknown compound D exhibits a strong...Ch. 21 - Prob. 21.86PCh. 21 - -D-Glucose, a hemiacetal, can be converted to a...Ch. 21 - 21.81 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 21.89PCh. 21 - Prob. 21.90PCh. 21 - Prob. 21.91PCh. 21 - 21.86 Draw stepwise mechanism for the following...
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- Explain why methyl trifluoroacetate, CF3CO2CH3, is more reactive than methyl acetate, CH3CO2CH3, in nucleophilic acyl substitution reactions.arrow_forwardWhich functional group has the maximum reactivity toward nucleophilic attack? a) acid chloride b) ketone c) ester d) amidearrow_forwardExplain why carboxylic acids do not undergo nucleophilic acyl substitution reactions with amines.arrow_forward
- Why is it not advisable to use aqueous hydrochloric acid in a Grignard reaction of a ketone? A) The Grignard reagent will react with the acid and cannot react with the ketone. B) The ketone will be protonated and will become unreactive. C) The ketone will form an unreactive enol. D) The Grignard reagent won't dissolve in aqueous solutionsarrow_forwardDraw a stepwise mechanism for the following substitution. Explain why 2-chloropyridine reacts faster than chlorobenzene in this type of reaction.arrow_forwardDraw the products formed when p-methylaniline (p-CH3C6H4NH2) istreated with following reagent. NaNO2, HClarrow_forward
- Not all aldehyde give a positve Bendicts test. Which of the follwing aldehydes do? a. d. b. e. c.arrow_forwardDeprotection or the removal; Draw out the mechanism of acetal protecting group to ketonearrow_forwardDescribe the way that the following compound could be synthesize from benzene.arrow_forward
- Rank the following compounds in order of increasing reactivity toward nucleophilic attack.arrow_forwardDraw the products formed when attached compound is treated with HNO3 and H2SO4. State whether the reaction occurs faster or slower than a similar reaction with benzene.arrow_forwardElectrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict themajor products of the reactions of naphthalene with the following reagents. f) fuming sulfuric acidarrow_forward
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