CNCT ORG CHEM 6 2020
6th Edition
ISBN: 9781266807244
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
Which aldoses are oxidized to optically inactive aldaric acids: (a) D-erythrose; (b) Dlyxose; (c) D-galactose?
Chapter 29 Solutions
CNCT ORG CHEM 6 2020
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
- 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.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
- Atorvastatin (Lipitor) is used to decrease patient serum cholesterol levels. It works by inhibiting an enzyme called HMG-COA reductase. See"Connections to Biological Chemistry" one synthesis of atorvastatin that produces the desired single enantiomer of the final product, the following reagents are used. Draw the structures of synthetic intermedi- ates A and B. In -Cl NaCN НО. A B DMSO Pyridinearrow_forwardA chiral alkyne A with molecular formula C6H10 is reduced with H2 and Lindlar catalyst to B having the R conguration at its stereogenic center. What are the structures of A and B?arrow_forwardAlkenes 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_forward
- Hydrogenation of alkene A with D2 in the presence of Pd-C affords asingle product B. Keeping this result in mind, what compound is formedwhen A is treated with each reagent: (a) mCPBA; (b) Br2, H2O followedby base? Explain these results.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
- (a) Give an acceptable name for each compound, (b) Draw the organic products formed when A or B is treated with each reagent: [1] H3O+; [2] −OH, H2O; [3] CH3CH2CH2MgBr (excess), then H2O; [4] LiAlH4, then H2O.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_forwardIdentify A, B, C, and D in the preceding problem if D is oxidized to an optically inactive aldaric acid; if A, B, and C are oxidized to optically active aldaric acids; and if interchanging the aldehyde and alcohol groups of A leads to a different sugar.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