Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 17, Problem 53P
Draw the products of the following reactions:
- a. 1,3-cyclohexanedione + LDA/THF, followed by allyl bromide
- b. γ-butyrolactone + LDA/THF, followed by methyl iodide
- c. 2,7-octanedione + sodium hydroxide
- d. diethyl 1,2-benzenedicarboxylate + sodium ethoxide: (1) slow addition of ethyl acetate; (2) HCl
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Identify products A and B from the given 1H NMR data.a. Treatment of CH2 = CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A?b. Treatment of acetone [(CH3)2C = O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1 H) ppm. What is the structure of B?
Draw the products of the following reactions:
a. 1,3-cyclohexanedione + LDATHF, followed by allyl bromide
b. y-butyrolactone + LDA/THF, followed by methyl iodide
c. 2,7-0ctanedione + sodium hydroxide
d. diethyl 1,2-benzenedicarboxylate + sodium ethoxide: (1) slow addition of ethyl acetate; (2) HCI
Draw the products of the following reactions:
a. diethyl heptanedioate: (1) sodium ethoxide; (2) HCl
b. pentanoic acid + PBr3 + Br2, followed by hydrolysis
c. acetone + LDA/THF: (1) slow addition of ethyl acetate; (2) HCl
d. diethyl 2-ethylhexanedioate: (1) sodium ethoxide; (2) HCl
e. diethyl malonate: (1) sodium ethoxide; (2) isobutyl bromide; (3) HCl, H2O + ∆
f. acetophenone + LDA/THF: (1) slow addition of diethyl carbonate; (2) HCl
Chapter 17 Solutions
Organic Chemistry (8th Edition)
Ch. 17.1 - Prob. 1PCh. 17.1 - Prob. 2PCh. 17.1 - Prob. 3PCh. 17.1 - Prob. 4PCh. 17.1 - Rank the compounds in each of the following groups...Ch. 17.2 - Explain why 92% of 2,4-pemtanedione exists as the...Ch. 17.3 - Draw the enol tautomers for each of the following...Ch. 17.3 - Prob. 8PCh. 17.4 - Prob. 9PCh. 17.4 - Prob. 10P
Ch. 17.5 - Show how the following compounds can be prepared...Ch. 17.6 - What compound is formed when a dilute solution of...Ch. 17.7 - Prob. 13PCh. 17.7 - Prob. 14PCh. 17.7 - How many stereoisomers are obtained from each of...Ch. 17.7 - Prob. 16PCh. 17.8 - Prob. 17PCh. 17.9 - Prob. 18PCh. 17.9 - What reagents should be used to prepare the...Ch. 17.10 - Prob. 20PCh. 17.10 - What aldehyde or ketone would be obtained when...Ch. 17.11 - Prob. 22PCh. 17.11 - How could you prepare the following compound using...Ch. 17.12 - Prob. 25PCh. 17.12 - What two carbonyl compound are required for the...Ch. 17.12 - Propose a mechanism for the following reaction:Ch. 17.13 - Draw the products of the following reactions:Ch. 17.13 - Prob. 29PCh. 17.13 - Prob. 30PCh. 17.14 - Prob. 31PCh. 17.15 - Write the mechanism for the reaction of a...Ch. 17.15 - Prob. 33PCh. 17.15 - Prob. 34PCh. 17.15 - Draw the product of the reaction of each of the...Ch. 17.16 - Draw the product obtained by heating each pair of...Ch. 17.16 - What two carbonyl compounds are needed to...Ch. 17.17 - Prob. 38PCh. 17.18 - Prob. 39PCh. 17.18 - Prob. 40PCh. 17.19 - Prob. 41PCh. 17.20 - Prob. 43PCh. 17.21 - Propose a mechanism for the formation of...Ch. 17.21 - Prob. 45PCh. 17.21 - a. If the biosynthesis of palmitic acid were...Ch. 17.21 - Prob. 47PCh. 17 - Prob. 48PCh. 17 - Prob. 49PCh. 17 - Number the following compounds in order of...Ch. 17 - The 1H NMR chemical shifts of nitromethane,...Ch. 17 - Prob. 52PCh. 17 - Draw the products of the following reactions: a....Ch. 17 - A racemic mixture of 2-methyl-1-phenyl-1-butanone...Ch. 17 - Draw the products of the following reaction:Ch. 17 - Prob. 56PCh. 17 - Prob. 57PCh. 17 - In the presence of excess base and excess halogen,...Ch. 17 - Identify A-L. (Hint: A shows three singles in its...Ch. 17 - Using cyclopentanone as the reactant, show the...Ch. 17 - Show how 4-methyl-3-hexanol can be synthesized...Ch. 17 - Show how the following compound can be synthesized...Ch. 17 - Show how the following compounds can be prepared...Ch. 17 - Prob. 64PCh. 17 - Prob. 65PCh. 17 - Indicate how each of the following compounds can...Ch. 17 - Prob. 67PCh. 17 - The ketone whose 1H NMR spectrum is shown here was...Ch. 17 - Indicate how the following compounds can be...Ch. 17 - Compound A with molecular formula C6H10 has two...Ch. 17 - Prob. 71PCh. 17 - Draw the products of the following reactions:Ch. 17 - Prob. 73PCh. 17 - a. Show how the amino acid alanine can be...Ch. 17 - Show how the following compounds can be...Ch. 17 - Prob. 76PCh. 17 - Explain why the following bromoketone forms...Ch. 17 - Prob. 78PCh. 17 - A carboxylic arid is formed when an -haloketone...Ch. 17 - An , -unsaturated carbonyl compound can be...Ch. 17 - What carbonyl compounds are required to prepare a...Ch. 17 - Prob. 82PCh. 17 - A Cannizzaro reaction is the reaction of an...Ch. 17 - Propose a mechanism for each of the following...Ch. 17 - The following reaction is known as the benzoni...Ch. 17 - Prob. 86PCh. 17 - Prob. 87PCh. 17 - Prob. 88PCh. 17 - Prob. 89PCh. 17 - Prob. 90PCh. 17 - Propose a mechanism for the following reaction:Ch. 17 - What reagents are required to convert the reactant...Ch. 17 - Starting with bromocyclohexane, how can each of...Ch. 17 - Describe how the following compounds can be...Ch. 17 - Prob. 4PCh. 17 - Describe three ways to synthesize the following...Ch. 17 - Explain why 92% of 2.4-pentanedione exists as the...Ch. 17 - Describe how the following compound can be...Ch. 17 - Prob. 8PCh. 17 - Prob. 9PCh. 17 - Prob. 10PCh. 17 - Show how the following compounds can be...
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
- The product of reaction between formaldehyde with 2-methyl propanal give 2,2-dimethyl-3-hydroxy propanal 2,2-dimethyl-3-hydroxy propanone 2,2-dimethyl-3-hydroxy propanoic acid 2,2-dimethyl-3-hydroxy propanol 4-phenyl-3-buten-2-one prepared from reaction between Benzaldehyde with acetic acid Benzaldehyde with acetaldehyde Benzaldehyde with formaldehyde Benzaldehyde with acetone Which predict product for reaction between heptane-6-one-1-al with sodium hydroxide * 1-(2-hydroxycyclopentyl) pentanone 1-(2-hydroxycyclopentyl) butanone 1-(2-hydroxycyclopentyl) ethanone 1-(2-hydroxycyclopentyl) propanonearrow_forwardShow the products from the reaction of p-bromoaniline with following reagents: a)CH3Cl(excess) b) HCl c) CH3COCl d) CH3MgBr e) CH3CH2Cl, AlCl3arrow_forwardHow might you convert geraniol into either ethyl geranylacetate or geranylacetone?arrow_forward
- What products are obtained from the reaction of the following compounds with LiAlH4 followed by treatment with dilute acid? a. ethyl butanoate c. methyl benzoate b. benzoic acid d. pentanoic acidarrow_forwardWhat compounds are formed from the reaction of benzoyl chloride with the following reagents? a. sodium acetate b. water c. excess dimethylamine d. aqueous HCl e. aqueous NaOH f. cyclohexanol g. excess benzylamine h. 4-chlorophenol i. isopropyl alcohol j. excess aniline k. potassium formatearrow_forwardThe reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This reaction, known as the Ritter reaction, doesnot work with primary alcohols. a. Propose a mechanism for the Ritter reaction.b. Why does the Ritter reaction not work with primary alcohols?c. How does the Ritter reaction differ from the acid-catalyzed hydrolysis of a nitrile to form an amide?arrow_forward
- 4. Draw a chemical reaction scheme that includes an arrow - pushing mechanism for each of the following reactions: a. Protonation of p-acetyl aniline by HCI followed by deprotonation with NaOH b. Deprotonation of benzoic acid by NaOH followed by protonation with HCIarrow_forwardAcetals are often prepared during the synthetic sequence to protect the carbonyl group of an aldehyde or ketone. Such an acetal is not reactive to each of the following reagents except: a.) LiAlH4 b.) PCC(Collins) c.) H3O+ d.) RMgBr e.) NaOHarrow_forwardPropose a mechanism for the reaction of acetic anhydride with water. a. How does this mechanism differ from the mechanism for the reaction of acetic anhydride with an alcohol?arrow_forward
- Arrange the compounds in order of INCREASING reactivity towards bromination. 1. Toluene, Nitrobenzene, Anisole, Aniline 2. Acetanilide, Benzaldehyde, Toluene, Iodobenzene 3. Acetophenone, Bromobenzene, Aniline, Phenolarrow_forwardPhosgene (COCl2) was used as a poison gas in World War I. What product would be formed from the reaction of phosgene with each of the following reagents? a. one equivalent of methanol b. excess methanol c. excess propylamine d. excess waterarrow_forward2. Draw the product of the reaction of cyclopentanone with each of the following reagents: a. Lithium aluminium hydride, followed by water b. Phenyllithium followed by dilute acid c. Aniline d. Chromic acid e. Sodium cyanide with addition of sulphuric acidarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Coenzymes and cofactors; Author: CH15 SWAYAM Prabha IIT Madras;https://www.youtube.com/watch?v=bubY2Nm7hVM;License: Standard YouTube License, CC-BY
Aromaticity and Huckel's Rule; Author: Professor Dave Explains;https://www.youtube.com/watch?v=7-BguH4_WBQ;License: Standard Youtube License