Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 5, Problem 5.22P
Interpretation Introduction
Interpretation:
Way in which racemization of trans-cycloalkane take place without breaking any bonds has to be determined. Also reason for trans-cyclononene racemize whereas trans-Cyclooctene does not under these conditions has to be explained.
Concept-Introduction:
Conformational isomerism is a type of stereoisomerism where isomers are able to get interconverted only by rotations about bonds that were formally single bonds.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
trans-Cyclooctene has been resolved, and its enantiomers are stable at room temperature. trans-Cyclononene has also been resolved, but it racemizes with a half-life of 4 min at 0°C. How can racemization of this cycloalkene take place without breaking any bonds? Why does trans-cyclononene racemize under these conditions but trans-cyclooctene does not? You will find it especially helpful to examine the molecular models of these cycloalkenes.
Using what you know about the conformational energetics of substituted cyclohexanes, predict which of the two decalin isomers is more stable. Explain your reasoning.
Which of the following statements about cycloaddition reactions is not true?
Cycloaddition reactions form a cyclic product with two new bonds.
The course of the reaction is determined by the symmetry of the molecular orbitals of the products.
Cycloaddition reactions are concerted.
Cycloaddition reactions are stereospecific.
Chapter 5 Solutions
Organic Chemistry
Ch. 5.1 - Calculate the index of hydrogen deficiency for...Ch. 5.1 - Prob. 5.2PCh. 5.2 - Write the IUPAC name of each alkene. (a) (b)Ch. 5.2 - Prob. 5.4PCh. 5.2 - Prob. 5.5PCh. 5.2 - Prob. 5.6PCh. 5.2 - Prob. 5.7PCh. 5.2 - Prob. 5.8PCh. 5 - Predict all approximate bond angles about each...Ch. 5 - Prob. 5.10P
Ch. 5 - The structure of 1,2-propadiene (allene) is shown...Ch. 5 - Prob. 5.12PCh. 5 - Draw structural formulas for these alkenes. (a)...Ch. 5 - Name these alkenes and cycloalkenes.Ch. 5 - Prob. 5.15PCh. 5 - Prob. 5.16PCh. 5 - Prob. 5.17PCh. 5 - For each molecule that shows cis, trans isomerism,...Ch. 5 - -Ocimene, a triene found in the fragrance of...Ch. 5 - Prob. 5.20PCh. 5 - Prob. 5.21PCh. 5 - Prob. 5.22PCh. 5 - Prob. 5.23PCh. 5 - Prob. 5.24PCh. 5 - Measure the CH3,CH3 distance in the...Ch. 5 - Prob. 5.26PCh. 5 - Measure the CCC and CCH bond angles in the...Ch. 5 - Prob. 5.28PCh. 5 - Prob. 5.29PCh. 5 - Prob. 5.30PCh. 5 - Prob. 5.31PCh. 5 - Prob. 5.32PCh. 5 - Prob. 5.33PCh. 5 - Pyrethrin II and pyrethrosin are two natural...Ch. 5 - Prob. 5.35PCh. 5 - Prob. 5.36PCh. 5 - Bromine adds to cis- and trans-2-butene to give...
Knowledge Booster
Similar questions
- Poly and B-Ryan are asked by their supervisor to synthesize (1R,3R)-1-chloro-1,3- dimethylcyclopentane. To accomplish their syntheses, Poly chooses to start from a trisubstituted alkene while B-Ryan chooses to start from a disubstituted alkene isomer. Poly's synthesis provides a mixture of isomers while B-Ryan's provides two stereoisomers. Both synthetic approaches are shown below. Me Me, Me, .CI Me HCI A B-Ryan's Synthesis Me 'CI + 75% 25% Ме Me Me Me... Me B Me C HCI A Poly's Synthesis -Me Ме 'CI 'CI + + Me.. .CI + a trace mixture ; of constitutional D Ме chloroalkane isomers Using your mechanistic knowledge of alkene reactions: (a) Explain the selectivity (regio and stereo) observed in B-Ryan's synthesis. (b) Propose a mechanism that accounts the formation of isomer C in Poly's synthesis. (c) Draw the major stereoisomer(s) formed in the "trace mixture of constitutional isomers" isolated in Poly's synthesis. 9.arrow_forwardFrom trans-1-chloro-2-isopropylcyclohexane, only 3-isopropylcyclohexene, the less substituted alkene, is formed. Using conformational analysis, explain why this product is observed. Also, will the E2 reaction with trans-1-chloro- 2-isopropylcyclohexane or cis-1-chloro-2-isopropylcyclohexane occur faster under the same basic conditions? CH;O Na* CH3OH CI trans-1-Chloro-2 (R)-3-Isopropylcyclohexene isopropylcyclohexanearrow_forwardG.170.arrow_forward
- Compound W, C8H₁7Br, and X, CgH₁7Cl, are products of the radical bromination (W), and chlorination (X), of 2,4-dimethylhexane. W and X are each chiral. W reacts readily in water to form a chiral substitution product Y, CgH17OH. Reaction of a single enantiomer of W produces a single enantiomer of Y as the only substitution product. X likewise reacts readily in water though at a slower rate than W; a chiral substitution product Z, C8H₁7OH, is again formed. Unlike w, however, reaction of a single enantiomer of X produces Z that is nearly racemic. Propose structures for W and X. 0 • Do not use stereobonds in your answer. In cases where there is more than one possible structure for each molecule, just give one for each. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. ● +▾ 99.8) ChemDoodleⓇ + v ChemDoodleⓇarrow_forwardCompound A, C₂H16 reacts with 1 molar equivalent(s) of hydrogen on catalytic hydrogenation. A undergoes reaction with ozone, followed by Zn treatment, to give: O CH3 O || CH3CCH₂CCH₂CCH3 CH3 Compound A Propose a structure for A. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one.arrow_forwardFor the alkenes shown below, consider the symmetry properties of the HOMO and the LUMO and decide whether this concerted cycloaddition reaction is likely to occur.arrow_forward
- Consider the reaction between (1S,3S)‑1‑chloro‑3‑methylcyclopentane and methanethiol in the presence of sodium hydroxide. (a) Draw the organic product and clearly indicate stereochemistry by showing the hydrogen on the chirality centers and using wedge and dash bonds. (b) Then analyze the stereochemistry of the product. racemic chiral achiral (1R, 3S) (1R, 3R) (1S, 3S)arrow_forwardEstimate the stabilization gained as a result of conjugation when 1,4-pentadiene is converted to trans-1,3-pentadiene. Note that the answer is not as simple as comparing the heats of hydrogenation of 1,4-pentadiene and trans-1,3pentadiene. Although the double bonds are moved from unconjugated to conjugated, the degree of substitution of one of the double bonds is also changed, in this case, from a monosubstituted double bond to a trans disubstituted double bond. To answer this question, you must separate the effect that is the result of conjugation from that caused by a change in the degree of substitution.arrow_forwardMono-chlorination of n-butane yields 1-chlorobutane (30%) and 2- chlorobutane (70%). If each C-H bond had the same reactivity, the expected ratio of 1-chlorobutane to 2-chlorobutane would be: 30% : 70% 40% : 60% 50% 50% 60% : 40% 70% : 30%arrow_forward
- The major product of the following reaction exists as two stereoisomers. Draw both isomers: show all hydrogen atoms in the structures. Use wedge and dash bonds to indicate the stereochemistry (you don’t need to draw wedge and dash bonds for C-H bonds of CH3 and CH2 groups). Assign stereo configuration of the asymmetric carbon atoms and write the relationship between two isomers.arrow_forwarddescribe about the stability of some compounds ( provide some examples) and intermediates such as double bonds (Zaitsev rule), carbocations, carbanions, and carbenes.arrow_forwardHydrohalogenation of alkenes in the presence of peroxide adds a halide at the vinyl position. Which halide can be used in UV-catalyzed hydrohalogenation reaction in the presence of diethyl ether to obtain alkyl halide. Note: Distillation of the diethyl ether used in the reaction resulted in a violent explosion. * Molecular fluorine, only molecular bromine, only Molecular chlorine only molecular iodine, only Bromine and Molecular Chlorine, only naharrow_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