Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 10.8, Problem 10.12P
α-Hydroxyketones and α-hydroxyaldehydes are also oxidized by treatment with periodic acid.
It is not the α-hydroxyketone or
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The following molecule belongs to a class of compounds called enediols; each carbon of
the double bond carries an-OH group. Draw structural formulas for the a-hydroxyketone
and the a-hydroxyaldehyde with which this enediol is in equilibrium.
CH-OH
a-Hydroxyaldehyde =
C-OH= a -Hydroxyketone
ČH3
An enediol
Acetylene reacts with
sodium amide in the
presence of propyl
halide
produces aldehyde
produces ketones
It produces 2-pentane
Hydration of aldehydes and ketones can be catalyzed by acid
or base. Bases catalyze hydration by:
protonating the carbonyl oxygen
making the carbonyl group more electrophilic
employing hydroxide ion, which is a better nucleophile than water
making the carbonyl group less electrophilic
shifting the equilibrium position of the reaction to favor products
Chapter 10 Solutions
Organic Chemistry
Ch. 10.1 - Write IUPAC names for these alcohols and include...Ch. 10.1 - Classify each alcohol as primary, secondary, or...Ch. 10.1 - Write IUPAC names for these unsaturated alcohols.Ch. 10.2 - Arrange these compounds in order of increasing...Ch. 10.2 - Prob. 10.5PCh. 10.4 - Predict the position of equilibrium for this...Ch. 10.5 - Show how to convert (R)-2-pentanol to...Ch. 10.6 - Draw structural formulas for the alkenes formed by...Ch. 10.6 - Propose a mechanism to account for this...Ch. 10.7 - Propose a mechanism to account for the following...
Ch. 10.7 - Prob. AQCh. 10.7 - Prob. BQCh. 10.7 - Prob. CQCh. 10.7 - Prob. DQCh. 10.7 - Which step in the reaction would you expect to be...Ch. 10.7 - Prob. FQCh. 10.7 - Prob. GQCh. 10.8 - Prob. 10.11PCh. 10.8 - Prob. AQCh. 10.8 - Prob. BQCh. 10.8 - Prob. CQCh. 10.8 - Why does nature use a reagent as complex as NAD+...Ch. 10.8 - -Hydroxyketones and -hydroxyaldehydes are also...Ch. 10.9 - Write IUPAC names for these thiols.Ch. 10 - Which are secondary alcohols?Ch. 10 - Name each compound.Ch. 10 - Prob. 10.16PCh. 10 - Name and draw structural formulas for the eight...Ch. 10 - Arrange these compounds in order of increasing...Ch. 10 - Arrange these compounds in order of increasing...Ch. 10 - Prob. 10.20PCh. 10 - Prob. 10.21PCh. 10 - Arrange the compounds in each set in order of...Ch. 10 - Prob. 10.23PCh. 10 - The decalinols A and B can be equilibrated using...Ch. 10 - Prob. 10.25PCh. 10 - Select the stronger acid from each pair and...Ch. 10 - Prob. 10.27PCh. 10 - In each equilibrium, label the stronger acid, the...Ch. 10 - Write equations for the reaction of 1-butanol with...Ch. 10 - Write equations for the reaction of 2-butanol with...Ch. 10 - Prob. 10.31PCh. 10 - When (R)-2-butanol is left standing in aqueous...Ch. 10 - Two diastereomeric sets of enantiomers, A/B and...Ch. 10 - Acid-catalyzed dehydration of 3-methyl-2-butanol...Ch. 10 - Show how you might bring about the following...Ch. 10 - Propose a mechanism for the following pinacol...Ch. 10 - Prob. 10.37PCh. 10 - Show how each alcohol or diol can be prepared from...Ch. 10 - Dihydropyran is synthesized by treating...Ch. 10 - Show how to convert propene to each of these...Ch. 10 - Prob. 10.41PCh. 10 - Prob. 10.42PCh. 10 - The tosylate of a primary alcohol normally...Ch. 10 - Prob. 10.44PCh. 10 - Show how to convert cyclohexene to each compound...Ch. 10 - Prob. 10.46PCh. 10 - Ethanol (CH3CH2OH) and dimethyl ether (CH3OCH3)...Ch. 10 - Prob. 10.48PCh. 10 - Prob. 10.49PCh. 10 - Prob. 10.50PCh. 10 - Write the products of the following sequences of...Ch. 10 - Alcohols are important for organic synthesis,...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Prob. 10.57PCh. 10 - Prob. 10.58PCh. 10 - Prob. 10.59P
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- 17-60 1-Propanol can be prepared by the reduction of an aldehyde, but it cannot be prepared by the acid catalyzed hydration of an alkene. Explain why it cannot be prepared from an alkene.arrow_forward17-72 The following molecule is an enediol; each carbon of the double bond carries an —OH group. Draw structural formulas for the hydroxyketone and the a-hydroxyaldehyde with which this enediol is in equilibrium.arrow_forward17-35 Suppose that you take a bottle of benzaldehyde (a liquid, bp 179°C) from a shelf and find a white solid in the bottom of the bottle. The solid turns litmus red; that is, it is acidic. Yet aldehydes are neutral compounds. How can you explain these observations?arrow_forward
- Esterification of Carboxylic Acids Provide the reactions (chemical equations) on esterification of the following acids: Ethanoic acid Butanoic acid Benzoic acid Acetic acid + methanol Acetic acid + ethanol Salicylic acid + methanol Acetic acid + benzyl alcoholarrow_forwardAldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule of alcohol gives an acetal and a molecule of water. ROH, H+ OH OR Aldehyde/ketone Alcohol ROH, H+ Draw the structural formulas for the hemiacetal and the acetal formed between the following compounds: OH OH OR OR • Use the wedge/hash bond tools to indicate stereochemistry where it exists. + H₂Oarrow_forwardhelparrow_forward
- 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.arrow_forwardA mixture of the compounds shown below is dissolved in cyclohexane. An aqueous solution of NaOH is added to the solution, and two layers are formed. Which compound(s) is(are) found in the aqueous layer? он HO Benzoic acid Beta-naphthol Naphthalene O Benzoic acid only O Beta-naphthol only O Naphthalene O Both Benzoic acid and beta-naphthol O Both beta-naphthol and naphthalenearrow_forwardAn organic chemistry student combines sodium amide and an alkyne. The major ion product of that reaction is then combined with an aldehyde, followed by a work-up with pyridine. Which of the following functional groups will be in the major product? aldehyde ketone alkyne alcohol alkene Grignard reagent O amidearrow_forward
- A synthetic organic molecule, G, which contains both aldehyde and ether functional groups, is subjected to a series of reactions in a multi-step synthesis pathway. In the first step, G undergoes a Wittig reaction, leading to the formation of an alkene, H. Subsequently, H is treated with an ozone (O3) reagent followed by a reducing agent in an ozonolysis reaction, resulting in the formation of two different products, I and J. Considering the functional groups present in G and the nature of the reactions involved, what are the most probable structures or functional groups present in products I and J? A. I contains a carboxylic acid group, and J contains an aldehyde group. B. I contains a ketone group, and J contains an alcohol group. C. I and J both contain aldehyde groups. D. I contains an ester group, and J contains a ketone group. Don't use chat gpt.arrow_forwardBenzene can be hydroxylated by treating it with hydrogen peroxide and a strong acid such as trifluoromethanesulfonic acid (TfOH). Propose amechanism for this reactionarrow_forward17-28 Show how acetaldehyde can form hydrogen bonds with water.arrow_forward
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