Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 18.12, Problem 18.13P
Propose mechanisms for
- a. the acid-catalyzed hydration of chloral to form chloral hydrate.
- b. the base-catalyzed hydration of acetone to form acetone hydrate.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
The reaction of an alkyl halide with
aceto acetic ester results to the
production of alan
O A. ketone
O B. secondary alcohol
C. primary alcohol
O D. acid
What explains why many aldehydes and ketones can undergo self- condensation reactions in basic conditions?
A. The alpha carbon can lose a proton and act like a nucleophile and the carbonyl carbon a an electrophile
B. The alpha carbon can gain a proton and act like an electrophile and the carbonyl carbon is a nucleophile
C. The oxygen of the carbonyl group can attack the carbon of the carbonyl group
D. Only esters can undergo self-condensation reactions
Which could explain the stronger acidity of phenols compared to alcohols. Why?
a.pi-electron delocalization
b.steric effect
c.hydrogen bonding
d.hyperconjugation
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
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- What is the major organic product obtained from the following reaction? A. aldehyde B. alcohol C. anhydride D. carboxylic acidarrow_forwardCompare aldehydes and ketones as to (Use acetaldehyde and acetone as examples). 1. Reaction with Tollen’s reagent 2. Reaction with Fehling’s reagent 3. Reaction with dilute NaOHarrow_forwardWhat reagents would you use to convert methyl propanoate to the following compounds? a. isopropyl propanoate b. sodium propanoate c. N-ethylpropanamide d. propanoic acidarrow_forward
- Complete these reactions. (a) (b)arrow_forwardEsters and amides are most easily made by nucleophilic acyl substitution reactions on… A. alcohols B. acid chlorides C. acid anhydrides D. carboxylates E. carboxylic acidsarrow_forwardConsider the structure of pent-2-ene, if it undergoes ozonolysis, which of the following final product is formed? a.Ethanal and Propanal b.Ethanal and Propanone c.CO2 and Propanal d.Ethanal and CO2arrow_forward
- Which of the following sets of reagents would not be an acceptable method for the preparation of ethylacetate? A. acetic acid, ethanol, and an acid catalyst B. Sodium acetate and ethanol C. Acetic anhydride and ethanol D. Sodium acetate and ethyliodidearrow_forward16. If toluene is synthesized from benzene and methyl chloride, what reaction has been observed? A. Halogenation B. Friedel-Craft's alkylation C. Sulfonation D. Nitrationarrow_forwardWhich of the following reactions will result in the formation of an acyl halide? Select one: a. The reaction of a carboxylic acid with phosphorus trichloride. b. The treatment of an alcohol with ethyl bromide. c. The reaction of an ester with hydrochloric acid. d. The addition of an alkene to dilute hydrochloric acid.arrow_forward
- 1. Which of the following organic compounds is the least polar? a. CH3CH2CHO b. CH3COCH3 c. CH3CH2CH2OH d. CH3CH2OCH3 e. CH3COOH 2. Which reagent can be used to convert acetic anhydride to acetic acid? a. NH3 b. CH3COO- c. CH3OH d. None of these e. H2Oarrow_forwardIdentify the role/function of the indicated molecule in the reaction? 1. LIAIH, ether 2. Но NaN3 Br -NH2 a. Nucleophile b. Electrophile c. Base O d. Acidarrow_forwardDescribe the reaction when a. Formaldehyde mixed with a fainty pink solution of potassium permanganate with a few drops of sulfuric acid. b. Acetaldehyde mixed with a fainty pink solution of potassium permanganate with a few drops of sulfuric acid. c. Benzaldehyde mixed with a fainty pink solution of potassium permanganate with a few drops of sulfuric acid.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Characteristic Reactions of Benzene and Phenols; Author: Linda Hanson;https://www.youtube.com/watch?v=tjEqEjDd87E;License: Standard YouTube License, CC-BY
An Overview of Aldehydes and Ketones: Crash Course Organic Chemistry #27; Author: Crash Course;https://www.youtube.com/watch?v=-fBPX-4kFlw;License: Standard Youtube License