Interpretation:
The structures for compounds A–J showing stereochemistry in a given sequence are to be written and the stereochemical relationship between (A and C) and (H and J) are to be determined.
Concept introduction:
Electrophiles are electron deficient species that have positive or partially positive charge. Lewis acids are electrophiles that accept electron pair.
Nucleophiles are electron rich species that have negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair.
Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a
Nucleophilic substitution reaction is a reaction in which an electron rich nucleophile attacks the positive or partial positive charge of an atom or a group of atoms to replace a leaving group.
The
The
An
The nucleophilic substitutions in which a nucleophile replaces a leaving group are known as
The stability of carbocation:
Enantiomers and diastereomers are two types of stereoisomers. Enantiomers share mirror image relationship and diastereomers are those in which stereochemistry differs at any one of the chiral centers.
Reaction of alkene with boron hydride followed by treatment with hydrogen peroxide, results in cis addition of hydrogen and hydroxyl groups around the double bond.
Reaction of alcohol with tosyl or mesyl chloride forms tosylates or mesylates, which retains the stereochemistry as the reaction is ester formation and does not involve the chiral carbon.
Tosylates or mesylates can undergo nucleophilic substitution with halides, hydroxides, and acetylides resulting in formation of products with inversion of configuration as the attack of nucleophile occurs at the back side.
Epichlorohydrin is a compound which contains epoxide and chloro substitution alkyl chain. It is formed when ring closure occurs between the hydroxyl and halogen of adjacent carbon atoms.
Want to see the full answer?
Check out a sample textbook solutionChapter 11 Solutions
Organic Chemistry
- (a) Draw the structure of (1E,4R)-1,4-dimethylcyclodecene. (b) Draw the enantiomer and name it, including its E,Z and R,S prefixes. (c) Draw two diastereomers and name them, including the E,Z and R,S prefixes.arrow_forward(a) What product is formed when triene N undergoes thermal electrocyclic ring closure? (b) What product is formed when triene N undergoes photochemical ring closure? (c) Label each process as conrotatory or disrotatory.arrow_forward(a) What product is formed when triene N undergoes thermal electrocyclic ring closure? (b)What product is formed when triene N undergoes photochemical ring closure? (c) Label each process as conrotatory or disrotatory.arrow_forward
- (a) What alkene yields A and B when it is treated with Br2 in CCl4? (b) What alkene yields C and D under the same conditions?arrow_forwardConsider the tetracyclic aromatic compound drawn below, with rings labeled as A, B, C, and D. (a) Which of the four rings is most reactive in electrophilic aromatic substitution? (b) Which of the four rings is least reactive in electrophilic aromatic substitution? (c) What are the major product(s) formed when this compound is treated with one equivalent of Br2?arrow_forwardAssign E or Z stereochemistry to each of the following alkenes, and convert each drawing into a skeletal structure (red = 0, yellow-green = Cl). (a) (b)arrow_forward
- The cis ketone A is isomerized to a trans ketone B with aqueous NaOH. A similar isomerization does not occur with ketone C. (a) Draw the structure of B using a chair cyclohexane. (b) Label the substituents in C as cis or trans, and explain the difference in reactivity.arrow_forward1 Provide the IUPAC name of the following compounds, with clear indication of stereochemistry for stereocenters and alkene. (a) (b) Br (c) Me. (d) Mearrow_forward(a) Draw the products (including stereoisomers) formed when 2methylhex-2-ene is treated with HBr in the presence of peroxides. (b) Draw the products (including stereoisomers) formed when (S)-2,4dimethylhex-2-ene is treated with HBr and peroxides under similar conditions.arrow_forward
- Chondrocole A is a marine natural product isolated from red seaweed that grows in regions of heavy surf in the Pacic Ocean. (a) Predict the solubility of chondrocole A in water and CH2Cl2. (b) Locate the stereogenic centers and label each as R or S. (c) Draw a stereoisomer and a constitutional isomer of chondrocole A.arrow_forwardGive IUPAC names for the following structures. (If appropriate, specify relative stereochemistry.) (a) (b) S Sarrow_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
- 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