ORGANIC CHEMISTRY
6th Edition
ISBN: 9781266633973
Author: SMITH
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 29, Problem 44P
Interpretation Introduction
Interpretation: The mechanism for the given reaction is to be drawn.
Concept introduction: In biological reactions, allylic carbocations are the intermediates that are required for the formation of Farnesyl diphosphate.
The general steps involved in the biological formation of Farnesyl diphosphate are stated below.
➢ The first step is the generation of allylic carbocation by the loss of the diphosphate group.
➢ The second step is the nucleophilic attack of isopentyl diphosphate to form new bond.
➢ The third step is the deprotonation to give final product.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Hydrogenation of alkene A with Dz in the presence of Pd-C affords a single product B. Keeping this result in mind, what
compound is formed when A is treated with each reagent: (a) MCPBA; (b) Br2, H,O followed by base? Explain these results.
D2
Pd-C
A
B
An aldose A, is reduced by sodium borohydride to an optically inactive alditol B. The Ruff degredation of A forms C. Oxidation of C by nitric acid generates the optically inactive diacid D. The ruff degreation of C forms D-glyceraldehyde. draw the structures for compounds A through D and discuss a mechanism for the reduction step using sodium borohydride
For alkenes A, B, C, and D:
(a) Rank A—D in order of increasing heat ofhydrogenation;
(b) rank A—D in order of increasing rate of reaction withH2, Pd-C;
(c) draw the products formed when each alkene is treated withozone, followed by Zn, H2O.
Chapter 29 Solutions
ORGANIC CHEMISTRY
Ch. 29.2 - Problem 31.1
One component of jojoba oil is a wax...Ch. 29.3 - Problem 31.2
How would you expect the melting...Ch. 29.3 - Problem 31.3
Draw the products formed when...Ch. 29.3 - Problem 31.4
The main fatty acid component of the...Ch. 29.3 - Prob. 5PCh. 29.7 - Problem 31.10
Locate the isoprene units in each...Ch. 29.7 - Problem 31.11
Locate the isoprene units in...Ch. 29.7 - Problem 31.12
Write a stepwise mechanism for the...Ch. 29.7 - Prob. 14PCh. 29.8 - Prob. 15P
Ch. 29.8 - Prob. 16PCh. 29.8 - Prob. 17PCh. 29 - 31.17 Locate the isoprene units in each...Ch. 29 - Prob. 25PCh. 29 - Locate the isoprene units in each compound. a. e....Ch. 29 - 31.27 Classify each terpene and terpenoid in...Ch. 29 - Prob. 33PCh. 29 - Draw three-dimensional structures f or each...Ch. 29 - Prob. 37PCh. 29 - Prob. 38PCh. 29 - Prob. 39PCh. 29 - Prob. 40PCh. 29 - 31.38 Draw the products formed when cholesterol is...Ch. 29 - 31.39 Draw a stepwise mechanism for the following...Ch. 29 - 31.40 Draw a stepwise mechanism for the following...Ch. 29 - Prob. 44P
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
- a.) Give an acceptable name for compound C. (b) Draw the organicproducts formed when C is treated with each reagent: [1] H3O+; [2] −OH,H2O; [3] CH3CH2CH2MgBr (excess), then H2O; [4] LiAlH4, then H2O.arrow_forward(a) What is the major alkene formed when A is dehydrated with H2SO4? (b) What is the major alkene formed when A is treated with POCl3 and pyridine? Explain why the major product is different in these reactions.arrow_forwardDienynes undergo metathesis to afford fused bicyclic ring systems. (a) Explain how A is converted to B. (b) Keeping this reaction in mind, draw the two products formed by dienyne metathesis of C.arrow_forward
- Alkenes can be converted to alcohols by hydroboration-oxidation. (a) Draw the structure of the alcohol or alcohols formed in the reaction sequence. Clearly indicate stereochemistry by drawing a wedged bond, a dashed bond and two O Hint in-plane bonds per each chiral carbon. Draw hydrogen atoms that are connected to wedge-and-dash bonds.(b) Characterize the product or products of the reactions. The first step of the reaction, hydroboration, involves addition of BH, to the double bond, with -BH, attached to one carbon and hydrogen Be sure to draw hydrogens on oxygen, where applicable. attached to the other. Consider both Rings the regioselectivity and the Select Draw More Erase stereochemistry of this addition. H Diborane, B,H,, is a source of borane, BH,, and can be used 1. B2H6, interchangeably. Diglyme is a solvent. diglyme 2. H2О2, НО", The product or products of the reaction are characterized as being O S. O racemic. O achiral. O R,S (and/or S,R). O R. O S,S. O R.R. O diastereomers.arrow_forwardA compound of cycloalkene can be prepared through dehydration of 2-methylcyclohexanol. a) Outline stepwise mechanism of the reactions b) Determine the major and minor products formed.arrow_forwardA D-aldopentose A is oxidized to an optically inactive aldaric acid with HNO3. A is formed by the Kiliani–Fischer synthesis of a D-aldotetrose B, which is also oxidized to an optically inactive aldaric acid with HNO3. What are the structures of A and B?arrow_forward
- 12.41 Hydrogenation of alkene A with D₂ in the presence of Pd-C affords a single product B. Keeping this result in mind, what compound is formed when A is treated with each reagent: (a) mCPBA; (b) Br2, H₂O followed by base? Explain these results. A D₂ Pd-C B H Harrow_forwardDraw a stepwise mechanism for the biological conversion of linalyl diphosphate to limonene.arrow_forwardDraw all of the substitution and elimination products formed from thegiven alkyl halide with each reagent: (a) CH3OH; (b) KOH. Indicate thestereochemistry around the stereogenic centers present in the products,as well as the mechanism by which each product is formed.arrow_forward
- Stereochemistry and pKa Ivermectin is an antibacterial and antiparascitic natural product that is produced by fermentation cultures of the bacteria Streptomyces avermectilis. It is an inexpensive and well-tolerated treatment for river blindness in humans caused by the parasitic nematode Onchocerce volvulus. It is also an excellent horse dewormer. There is no scientific evidence that is has any effect on SARS-COV2. Please examine the chemical structure carefully and answer the questions that follow. In the circles please assign (E) or (Z) configuration to the double bonds indicated with an arrow. In the boxes please assign the absolute configuration i.e. (R) or (S) to the stereogenic centers indicated with an arrow. In the triangle please provide an approximate value for the pKa of the protons indicated with an arrow. Meo HO O MeO НО HOarrow_forwardQuestion 5.35arrow_forwardDraw all stereoisomers formed when each alkene is treated with mCPBA.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 Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning