Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 18, Problem 18.41SP
Acetals can serve as protecting groups for 1,2-
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Br2, H3O+
གོ་ཤི་ན་ཤི་
H3C CH3
CH3
CH3
Aldehydes and ketones can be halogenated at their a-position by reaction with Cl₂, Br2, or 12, under acidic conditions. Using Br2 under acidic conditions, an intermediate enol is formed which adds
bromine at the a-position. The reaction stops after the addition of one bromine because the electron-withdrawing halogen decreases the basicity of the carbonyl oxygen, making the protonation less
favorable.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
:OH
:OH
Br-Br
H3C
H3C.
Br
Br
CH₂
H₂
H3C CH3
H3C CH3
2b
Give the products of the following substitution reactions. For every reaction, show electron pairs on both nucleophile and leaving group.
CH3
གོན་ནི། ཡོན་
Br₂,
H₂C
CH₂Br
H3C CH3
H₂C CH3
Aldehydes and ketones can be halogenated at their a-position by reaction with Cl₂, Br2, or 12, under acidic conditions. Using Br₂ under acidic conditions, an intermediate enol is formed which adds
bromine at the a-position. The reaction stops after the addition of one bromine because the electron-withdrawing halogen decreases the basicity of the carbonyl oxygen, making the protonation less
favorable.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
:0:
:OH
н-он
H-OH₂
H₂O
H₂C.
H3C.
CH3
CH3
H3C CH3
H3C CH3
Σα
Chapter 18 Solutions
Organic Chemistry (9th Edition)
Ch. 18.3 - Give the IUPAC name and (if possible) a common...Ch. 18.5D - NMR spectra for two compounds are given here,...Ch. 18.5D - Why were no products from the McLafferty...Ch. 18.5D - Use equations to show the fragmentation leading to...Ch. 18.5E - Prob. 18.5PCh. 18.7D - Show how you would synthesize each compound from...Ch. 18.8 - Prob. 18.7PCh. 18.9 - Predict the products of the following reactions....Ch. 18.9 - Show how the following transformations may be...Ch. 18.10 - Prob. 18.10P
Ch. 18.11 - Show how you would accomplish the following...Ch. 18.11 - Prob. 18.12PCh. 18.12 - Propose mechanisms for a. the acid-catalyzed...Ch. 18.12 - Rank the following compounds in order of...Ch. 18.13 - Prob. 18.15PCh. 18.13 - Show how you would accomplish the following...Ch. 18.14 - Prob. 18.17PCh. 18.14 - Prob. 18.18PCh. 18.14 - Prob. 18.19PCh. 18.14 - Prob. 18.20PCh. 18.15 - 2,4-Dinitrophenylhydrazine is frequently used for...Ch. 18.15 - Prob. 18.22PCh. 18.15 - Prob. 18.23PCh. 18.16 - Prob. 18.24PCh. 18.16 - Prob. 18.25PCh. 18.16 - Show what alcohols and carbonyl compounds give the...Ch. 18.16 - In the mechanism for acetal hydrolysis shown, the...Ch. 18.16 - Prob. 18.28PCh. 18.17 - Show how you would accomplish the following...Ch. 18.18 - Prob. 18.30PCh. 18.18 - Prob. 18.31PCh. 18.18 - Prob. 18.32PCh. 18.18 - Show how Wittig reactions might be used to...Ch. 18.19 - Predict the major products of the following...Ch. 18.20C - Prob. 18.35PCh. 18.20C - Predict the major products of the following...Ch. 18 - Draw structures of the following derivatives. a....Ch. 18 - Prob. 18.38SPCh. 18 - Predict the major products of the following...Ch. 18 - Rank the following carbonyl compounds in order of...Ch. 18 - Acetals can serve as protecting groups for...Ch. 18 - Sketch the expected proton NMR spectrum of...Ch. 18 - A compound of formula C6H10O2 shows only two...Ch. 18 - The proton NMR spectrum of a compound of formula...Ch. 18 - The following compounds undergo McLafferty...Ch. 18 - An unknown compound gives a molecular ion of m/z...Ch. 18 - Show how you would accomplish the following...Ch. 18 - Prob. 18.48SPCh. 18 - Prob. 18.49SPCh. 18 - Propose mechanisms for the following reactions.Ch. 18 - Show how you would accomplish the following...Ch. 18 - Show how you would synthesize the following...Ch. 18 - Predict the products formed when cyclohexanone...Ch. 18 - Predict the products formed when...Ch. 18 - Show how you would synthesize octan-2-one from...Ch. 18 - Prob. 18.56SPCh. 18 - Both NaBH4 and NaBD4 are commercially available,...Ch. 18 - When LiAIH4 reduces 3-methylcyclopentanone, the...Ch. 18 - Prob. 18.59SPCh. 18 - Show how you would accomplish the following...Ch. 18 - There are three dioxane isomers 1,2-dioxane,...Ch. 18 - Two structures for the sugar glucose are shown on...Ch. 18 - Prob. 18.63SPCh. 18 - Prob. 18.64SPCh. 18 - Prob. 18.65SPCh. 18 - Prob. 18.66SPCh. 18 - Within each set of structures, indicate which will...Ch. 18 - Prob. 18.68SPCh. 18 - Prob. 18.69SPCh. 18 - Prob. 18.70SPCh. 18 - The UV spectrum of an unknown compound shows...Ch. 18 - a. Simple aminoacetals hydrolyze quickly and...Ch. 18 - The mass spectrum of unknown compound A shows a...Ch. 18 - Prob. 18.74SPCh. 18 - Prob. 18.75SPCh. 18 - Prob. 18.76SPCh. 18 - Prob. 18.77SP
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- Some alcohols undergo rearrangement or other unwanted side reactions when they dehydrate in acid. Alcohols may be dehydrated under mildly basic conditions using phosphorus oxychloride (POCl3) in pyridine. The alcohol reacts with phosphorus oxychloride much like it reacts with tosyl chloride, displacing a chloride ion from phosphorus to give an alkyl dichlorophosphate ester. The dichlorophosphate group is an outstanding leaving group. Pyridine reacts as a base with the dichlorophosphate ester to give an E2 elimination. Propose a mechanism for the dehydration of cyclohexanol by POCl3 in pyridine.arrow_forwardH3C OH 1. Br2, PBг3 2. H₂O H3C OH Br The a-bromination of carbonyl compounds by Br₂ in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br2 reacts in an a-substitution reaction. Hydrolysis of the acid bromide completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br Br зь P-Br Br H₂C H₂C SH Br Brarrow_forwardWrite the mechanisms for the following reactions bellow, justifying each substitution position.arrow_forward
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