Interpretation: The starting material of each of the two examples in the textbook should be replaced with one of its diastereomers and the product of SN2 displacement with the nucleophile shown should be written.
Concept Introduction:
Diastereomers are stereoisomers which are not mirror images of one another. Stereoisomers with two or more stereocenters can be diastereomers.
SN2 reactions are a type of nucleophilic substitution reactions. In SN2reactions, the addition of the nucleophile and the departure of the leaving group occur simultaneously. So, the nucleophile attacks the molecule from the opposite side of the leaving group. As a result, the geometry of the molecule changes and the stereochemical configuration of the molecule is inverted.
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Organic Chemistry: Structure and Function
- (c) Hydrolysis of the haloalkane shown below results in the formation of two alcohols B and C that are stereoisomers of each other. Give the structures of the alcohols B and C and propose a mechanism for their formation ensuring that you explain the stereochemical outcome observed. H3CH2C CH3 H20, heat Br B + Carrow_forwardThe reaction of 1-iodopropane with potassium thiocyanate (KSCN) in certain solvents results in the formation of two isomeric products, propylthiocyanate and propylisothiocyanate (see scheme below), via the SN2 reaction mechanism. Attempts to prepare a similar mixture of these same isomeric products (propylthiocyanate and propylisothiocyanate) starting from 1-propene is illustrated below. Despite the strong acidity of thiocyanic acid (recall pKa = 1.1), this addition reaction does not lead to either of the products indicated. Based on your knowledge of alkene addition reactions, explain this experimental result.arrow_forwardFollowing are diastereomers (A) and (B) of 3-bromo-3,4-dimethylhexane. On treat- ment with sodium ethoxide in ethanol, each gives 3,4-dimethyl-3-hexene as the major product. One diastereomer gives the E alkene, and the other gives the Z alkene. Which diastereomer gives which alkene? Account for the stereoselectivity of each B-elimination. H C-C Mẹ Me Br H Ме Br C-C Me Et Et Et Et (A) (В)arrow_forward
- 3. Isoerythrogenic acid, C18H26O2, is an acetylenic fatty acid that turns a vivid blue on exposure to UV light. On Catalytic hydrogenation over a palladium catalyst, five molar equivalents of hydrogen are absorbed, and stearic acid, CH3(CH2)16CO2H, is produced. Ozonolysis of isoerythrogenic acid yields the following products: formaldehyde, CH2O, malonic acid, HO2CCH2CO2H, adipic acid, HO2C(CH2)4CO2H, and the aldehyde carboxylic acid, OHC(CH2)6CO2H. Provide a structure for isoerythrogenic acid.arrow_forwardCH3 Br,/FeBr3 C3H;BrO 5 Using resonance structures, justify whether the acetyl group of compound 5 will direct the bromination reaction to the meta or ortho/para positions.arrow_forwardAlkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions -X티 Hö: H-O -CH3 -CH3 H30*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. For each reaction, fill in the missing starting material, reagents, or products. Some reactions have multiple possible answers. Where reagents are missing, more than one step may be needed. Depict all stereochemical details clearly when appropriate. (а) OH CH, (b) (1) excess O3 H3C (2) (CH3)2S `CH3 (c) (1) excess O3 2 CH3 (2) excess (CH3)2S (d) (1) BH3 (2) Н.О2 NaOH H20arrow_forwardChemistry (ii) Would you expect the rate of hydrolysis of methyl-p-fluorobenzoate (X = F) to be substantially greater than, significantly less than, or about the same as that of the unsubstituted compound; Ox (p-F) = 0.06? Give a short justification of your answer – calculations are unnecessary.arrow_forward
- The reaction of 1-bromopropane and sodium hydroxide in ethanol occurs by an SN2mechanism. What happens to the rate of this reaction under the following conditions?(a) The concentration of NaOH is doubled.(b) The concentrations of both NaOH and 1-bromopropane are doubled.(c) The volume of the solution in which the reaction is carried out is doubled.arrow_forwardProvide the systematic name for each of the following isomeric esters with the chemical formula C-H₁2O₂. (Be sure to indicate double bond stereochemistry using (E)/(Z) notation. Indicate stereochemistry in rings with the terms cis or trans. It is not necessary to use italics in writing compound names.) ball & stick - + labels ball & stick- + labels ball & stick + labels 12arrow_forwardTwo substitution products result from the reaction between 3-chloro-3-methyl-1- butene with sodium acetate (CH3COO – Na +) in acetic acid under SN1. Identify the products.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning