Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 18.9, Problem 18P
Interpretation Introduction
Interpretation:
The structure should be drawn for the decarboxylation of the pyruvate –TPP intermediate and the decarboxylation of a Beta – keto group and then similarity between these two structures has to be shown.
Concept introduction:
Thiamine pyrophosphate (TPP) is the coenzyme required by enzymes that catalyse the transfer of an acyl group.
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Consider the following nucleophilic substitution reaction. The compound listed above the arrow is the solvent for the reaction. If nothing is listed over the arrow,
then the nucleophile is also the solvent for the reaction.
Part 1 of 2
Br
CH,CN
+ I¯
What is the correct mechanism for the reaction? Select the single best answer.
@SN2
○ SN 1
Part: 1/2
Part 2 of 2
Draw the products for the reaction. Include both the major organic product and the inorganic product. If more than one stereoisomer is possible, draw
only one stereoisomer. Include stereochemistry where relevant.
Click and drag to start drawing a
structure.
X
હૈ
20.33 Think-Pair-Share
(a) Rank the following dienes and dienophiles in order of increasing reactivity in the
Diels-Alder reaction.
(i)
CO₂Et
(ii)
COEt
||
CO₂Et
MeO
MeO
(b) Draw the product that results from the most reactive diene and most reactive
dienophile shown in part (a).
(c) Draw a depiction of the orbital overlap involved in the pericyclic reaction that oc-
curs between the diene and dienophile in part (b).
(d) Is the major product formed in part (b) the endo or exo configuration? Explain
your reasoning.
20.40 The following compound undergoes an intramolecular Diels-Alder reaction to give a
tricyclic product. Propose a structural formula for the product.
CN
heat
An intramolecular
Diels-Alder adduct
Chapter 18 Solutions
Essential Organic Chemistry (3rd Edition)
Ch. 18.1 - Prob. 1PCh. 18.2 - If H218O were used to hydrolyze lysozyme, which...Ch. 18.3 - Which of the following amino acid side chains can...Ch. 18.3 - Arginine and lysine side chains fit into trypsins...Ch. 18.4 - Which of the following amino acid side chains can...Ch. 18.4 - Prob. 6PCh. 18.5 - Prob. 7PCh. 18.5 - Draw the mechanism for the hydroxide-ion-catalyzed...Ch. 18.5 - What advantage does the enzyme gain by forming an...Ch. 18.7 - Prob. 10P
Ch. 18.7 - Prob. 11PCh. 18.8 - How many conjugated double bonds are there in a....Ch. 18.8 - Instead of adding to the 4a-position and...Ch. 18.8 - In succinate dehydrogenase, FAD is covalently...Ch. 18.8 - Prob. 15PCh. 18.9 - Acetolactate synthase is another TPP-requiring...Ch. 18.9 - Acetolactate synthase can also transfer the acyl...Ch. 18.9 - Prob. 18PCh. 18.9 - Prob. 19PCh. 18.10 - Prob. 21PCh. 18.11 - Prob. 23PCh. 18.11 - Which compound is more easily decarboxylated?Ch. 18.11 - Explain why the ability of PLP to catalyze an...Ch. 18.11 - Explain why the ability of PLP to catalyze an...Ch. 18.12 - What groups are interchanged in the following...Ch. 18.13 - Why is the coenzyme called tetrahydrofolate?Ch. 18.13 - What amino acid is formed by the following...Ch. 18.13 - How do the structures of tetrahydrofolate and...Ch. 18.13 - What is the source of the methyl group in...Ch. 18 - Prob. 32PCh. 18 - Prob. 33PCh. 18 - From what vitamins are the following coenzymes...Ch. 18 - Prob. 35PCh. 18 - For each of the following reaction, name both the...Ch. 18 - Explain why serine proteases do not catalyze...Ch. 18 - Prob. 38PCh. 18 - For each of the following enzyme catalyzed...Ch. 18 - Trisephosphate isomerase (TIM) catalyzes the...Ch. 18 - Prob. 41PCh. 18 - What acyl groups have we seen transferred by...Ch. 18 - When UMP is dissolved in T2O, exchange of T for H...Ch. 18 - Prob. 44PCh. 18 - When transaminated, the three branched-chain amino...Ch. 18 - Aldolase shows no activity if it is incubated with...
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- What is the reaction mechanism for this?arrow_forwardWhat is the reaction mechanism for this?arrow_forwardCurved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. + Drawing Arrows CH3ONA, CH3OH heat : Br:O Na → H H Br Na + H H H H H :0: .H + Undo Reset Done Q CH3 Drag To Pan +arrow_forward
- What is the reaction mechanism for this?arrow_forward20.19 Predict the structure of the major 1,2-addition product formed by reaction of one mole of Cl₂ with 3-methylenecyclohexene. Also predict the structure of the 1,4-addition product formed under these conditions. 20.20 Which of the two molecules shown do you expect to be the major product formed by 1,2-addition of HCI to cyclopentadiene? Explain. Cyclopentadiene + HC 3-Chlorocyclopentene (racemic) or 4-Chlorocyclopentene (racemic)arrow_forward20.35 Propose structural formulas for compounds A and B and specify the configuration of compound B. EtO₂C 250°C C14H2004 CO₂Et 1. Oso, then NaHSO3 2. HIO4 C14H2006 A Barrow_forward
- 20.21 Predict the major product formed by 1,4-addition of HCI to cyclopentadiene. 20.22 Draw structural formulas for the two constitutional isomers with the molecular for- mula C₂H,Br, formed by adding one mole of Br, to cyclopentadiene.arrow_forwardAdd substituents to draw the conformer below (sighting down the indicated bond), then rotate the back carbon to provide the conformation that will be capable of an E2 elimination. R/S stereochemistry is graded. + I I H CH3 Ph Досн Br OCH 3 Drawing Q H Atoms, Bonds and Rings Charges Tap a node to see suggestions. H H H H H Undo Reset Remove Done Rotatearrow_forward20.17 Predict the structure of the major product formed by 1,2-addition of HBr to 3-methylenecyclohexene. 3-Methylenecyclohexene 20.18 Predict the major product formed by 1,4-addition of HBr to 3-methylenecyclohexene.arrow_forward
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