
Organic Chemistry Study Guide and Solutions Manual, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134649771
Author: Paula Yurkanis Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Question
Chapter 17, Problem 86P
Interpretation Introduction
Interpretation: The carbon that will be labeled in orsellinic acid has to be predicted.
Concept introduction: The orsellinic acid is most commonly found in lichens. It can be synthesized from the condensation of acetyl thioester and malonyl thioester. The synthesis involved the formation of various intermediates. The synthesis involves one molecule of acetyl thioester and three molecules of malonyl thioester. A ring-closure takes place to form a cyclic intermediate which on dehydrogenation forms orsellinic acid.
Expert Solution & Answer

Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Predict the major organic product(s) of the following reactions. Indicate which of the following mechanisms is in operation: SN1, SN2, E1, or E2.
(c)
(4pts)
Mechanism:
heat
(E1)
CH3OH
+
1.5pts each
_E1 _ (1pt)
Br
CH3OH
(d)
(4pts)
Mechanism:
SN1
(1pt)
(e)
(3pts)
1111 I
H
10
Ill!!
H
LDA
THF (solvent)
Mechanism: E2
(1pt)
NC
(f)
Bri!!!!!
CH3
NaCN
(3pts)
acetone
Mechanism: SN2
(1pt)
(SN1)
-OCH3
OCH3
1.5pts each
2pts for either product
1pt if incorrect
stereochemistry
H
Br
(g)
“,、
(3pts)
H
CH3OH
+21
Mechanism:
SN2
(1pt)
H
CH3
2pts
1pt if incorrect
stereochemistry
H
2pts
1pt if incorrect
stereochemistry
A mixture of butyl acrylate and 4'-chloropropiophenone has been taken for proton NMR analysis. Based on this proton NMR, determine the relative percentage of each compound in the mixture
Chapter 17 Solutions
Organic Chemistry Study Guide and Solutions Manual, Books a la Carte Edition (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
Similar questions
- Q5: Label each chiral carbon in the following molecules as R or S. Make sure the stereocenter to which each of your R/S assignments belong is perfectly clear to the grader. (8pts) R OCH 3 CI H S 2pts for each R/S HO R H !!! I OH CI HN CI R Harrow_forwardCalculate the proton and carbon chemical shifts for this structurearrow_forwardA. B. b. Now consider the two bicyclic molecules A. and B. Note that A. is a dianion and B. is a neutral molecule. One of these molecules is a highly reactive compound first characterized in frozen noble gas matrices, that self-reacts rapidly at temperatures above liquid nitrogen temperature. The other compound was isolated at room temperature in the early 1960s, and is a stable ligand used in organometallic chemistry. Which molecule is the more stable molecule, and why?arrow_forward
- A mixture of C7H12O2, C9H9OCl, biphenyl and acetone was put together in a gas chromatography tube. Please decide from the GC resutls which correspond to the peak for C7,C9 and biphenyl and explain the reasoning based on GC results. Eliminate unnecessary peaks from Gas Chromatography results.arrow_forwardIs the molecule chiral, meso, or achiral? CI .CH3 H₂C CIarrow_forwardPLEASE HELP ! URGENT!arrow_forward
- Identify priority of the substituents: CH3arrow_forwardHow many chiral carbons are in the molecule? OH F CI Brarrow_forwardA mixture of three compounds Phen-A, Acet-B and Rin-C was analyzed using TLC with 1:9 ethanol: hexane as the mobile phase. The TLC plate showed three spots of R, 0.1 and 0.2 and 0.3. Which of the three compounds (Phen-A; Acet-B or Rin-C) would have the highest (Blank 1), middle (Blank 2) and lowest (Blank 3) spot respectively? 0 CH: 0 CH, 0 H.C OH H.CN OH Acet-B Rin-C phen-A A A <arrow_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 LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning

Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning


Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning