Concept explainers
Consider the following sequence of reactions, taken from the early steps in a synthesis of ?-fluorooleic acid, a toxic natural compound from an African shrub. (?-Fluorooleic acid, also called “ratsbane,” has been used to kill rats and also as an arrow poison in tribal warfare. Two more steps beyond those below are required to complete its synthesis.)
(i) 1-Bromo-8-fluorooctane+sodium acetylide (the sodium salt of ethyne)
(ii) Compound
(iii) Compound
(iv) Compound
(a) Elucidate the structures of compounds A, B, C, and D above.
(b) Write the mechanism for each of the reactions above.
(c) Write the structure of the transition state for each reaction.
Want to see the full answer?
Check out a sample textbook solutionChapter 6 Solutions
ORGANIC CHEM LL W/WILEYPLUS BLCKBRD >I
Additional Science Textbook Solutions
Chemistry: The Central Science (14th Edition)
The Organic Chem Lab Survival Manual: A Student's Guide to Techniques
Essential Organic Chemistry (3rd Edition)
Chemistry: A Molecular Approach
Chemistry: Structure and Properties
- 4. identify the structure of A and B in the following synthetic scheme: Write out complete reactions for each step, showing the structure of all reactants and products. (a) cyclohexanol +Na2Cr2O7/H2SO4, H2O -------> A (b) A + Et2NH/H2SO4 ----->Barrow_forward(a) How will you convert:(i) Benzene to acetophenone (ii) Propanone to 2-Methylpropan-2-ol(b) Give reasons :(i) Electrophilic substitution in benzoic acid takes place at meta position.(ii) Carboxylic acids are higher boiling liquids than aldehydes, ketones and alcohols of comparable molecular masses.(iii) Propanal is more reactive than propanone in nucleophilic addition reactions.arrow_forwardStarting from bromoethane, the formation of which of the following compound requires more than one step of reaction? 2 (a) Methoxyethane (b) Ethanol (c) Ethanoic acid (d) Ethenearrow_forward
- How would you obtain(i) Picric acid (2, 4, 6-trinitrophenol) from phenol,(ii) 2-Methylpropene from 2-methylpropanol?arrow_forward(b) Consider the reaction of 1-bromobutane with a large excess of ammonia (NH3). Draw the reactants, the transition state, andthe products. Note that the initial product is the salt of an amine (RNH3+ Br - ), which is deprotonated by the excess ammonia to give the amine.arrow_forwardGive the structures of the products you would expect when each alcohol reacts with(1) HCl, ZnCl2; (2) HBr; (3) PBr3; (4) P>I2; and (5) SOCl2.(a) butan-1-ol (b) 2-methylbutan-2-ol(c) 2,2-dimethylbutan-1-ol (d) cis-3-methylcyclopentanolarrow_forward
- An organic compound A of unknown structure was found to have a molecular formula C8H16. When A was poured in water and heated, compound B having a molecular formula C8H18O was formed. B upon heating with sulfuric acid was converted to C as the major product which is identical to A. Ozonolysis of C gave one molecule each of two different products D and E, both having a molecular formula C4H8O. Write the reactions involved and determine the structure of A,B,C,D and E.arrow_forward11:43 Q1. (a) (c) (d) (b) Two stereoisomers of but-2-ene are formed when 2-bromobutane reacts with ethanolic potassium hydroxide. (i) Explain what is meant by the term stereoisomers. Library Name and outline a mechanism for the reaction of 2-bromo-2-methylpropane with ethanolic potassium hydroxide to form the alkene 2-methylpropene, (CH3)2C=CH₂ Name of mechanism Mechanism (ii) Draw the structures and give the names of the two stereoisomers of but-2-ene. Stereoisomer 1 Name (iii) Name this type of stereoisomerism. Select Name Stereoisomer 2 When 2-bromo-2-methylpropane reacts with aqueous potassium hydroxide, 2-methylpropan-2-ol is formed as shown by the following equation. CH3 H₂C-C-CH3 + KOH Br Page 2 of 14 CH3 H3C-C-CH3 + KBr ОН State the role of the hydroxide ions in this reaction. Write an equation for the reaction that occurs when CH3CH₂CH₂CH₂Br reacts with an excess of ammonia. Name the organic product of this reaction. Equation Name of product 9,284 Photos, 1,166 Videos For You…arrow_forwardThe odor of ripe bananas and many other fruits is due to the presence of esters. For example: Banana oil (isopentyl acetate) (a) Write the name (common or IUPAC) of the ester responsible for the fragrance of the following: pineapple, orange, apple, peach, & lavender (b) Choose one fragrant from (a) and name the alcohol and the carboxylic acid needed to synthesize this ester. (c) Show the detailed mechanism of the Fischer Esterification reaction that will be involved in the synthesis of the fragrant you have chosen in part (a).arrow_forward
- The following compounds are given to you:2-Bromopentane, 2-Bromo-2-methylbutane, 1-Bromopentane(i) Write the compound which is most reactive towards SN2 reaction.(ii) Write the compound which is optically active.(iii) Write the compound which is most reactive towards P-elimination reaction.arrow_forward1. b) Show the MECHANISM for the POLAR addition of molecular chlorine to cyclopentane. c) The reaction of toluene and ethylbenzene was through the alkyl groups, -CH 3 and -CH 2 CH 3, respectively. Why didn’t xylene, which has TWO methyl groups, react with bromine in the time allotted?arrow_forwardWrite the structure of the major organic product formed in the reaction of 1-pentene with each of the following: (a) Hydrogen chloride (b) Dilute sulfuric acid (c) Diborane in diglyme, followed by basic hydrogen peroxide (d) Bromine in carbon tetrachloride (e) Bromine in water (f) Peroxyacetic acid (g) Ozone (h) Product of part (g) treated with zinc and water (i) Product of part (g) treated with dimethyl sulfide (CH3)2Sarrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY