Following are two diastereomers of 3-bromo-3,4-dimethylhexane. On treatment 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 the E alkene? Me Br Ме Br Me H Mer Et Et b Et Et a a Following are two diastereomers of 3-bromo-2,3,4-trimethylhexane. On treatment with sodium ethoxide in ethanol, each gives 2,3,4-trimethyl-3-hexene as the major product. One diastereomer gives the E alkene, and the other gives the Z alkene. Which diastereomer gives the Z alkene? Me H Me Me Br Et Me Br Et iPr H iPr a b Following are two diastereomers of 3-bromo-4-ethyl-2,3,5-trimethylhexane. On treatment with sodium ethoxide in ethanol, each gives 3-ethyl-2,4,5-trimethyl-3-hexene as the major product. One diastereomer gives the E alkene, and the other gives the Z alkene. Which diastereomer gives the Z alkene? Br iPr H H Br Me iPr iPr Et Ме Et iPr a b b Ill

Following are two diastereomers of 3-bromo-3,4-dimethylhexane. On treatment 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 the E alkene? Me Br Ме Br Me H Mer Et Et b Et Et a a Following are two diastereomers of 3-bromo-2,3,4-trimethylhexane. On treatment with sodium ethoxide in ethanol, each gives 2,3,4-trimethyl-3-hexene as the major product. One diastereomer gives the E alkene, and the other gives the Z alkene. Which diastereomer gives the Z alkene? Me H Me Me Br Et Me Br Et iPr H iPr a b Following are two diastereomers of 3-bromo-4-ethyl-2,3,5-trimethylhexane. On treatment with sodium ethoxide in ethanol, each gives 3-ethyl-2,4,5-trimethyl-3-hexene as the major product. One diastereomer gives the E alkene, and the other gives the Z alkene. Which diastereomer gives the Z alkene? Br iPr H H Br Me iPr iPr Et Ме Et iPr a b b Ill

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter9: Nucleophilic Substitution And Β-elimination

Section: Chapter Questions

Problem 9.39P: Following are diastereomers (A) and (B) of 3-bromo-3,4-dimethylhexane. On treatment with sodium...

See similar textbooks

Similar questions

Reaction of HBr with 2-methylpropene yields 2-bromopropane. What is the structure of the carbocation intermediate formed during the reaction? Show the mechanism of the reaction.
5. Compound A, C 10H 18O, undergoes reaction with dilute H 2SO 4 at 50 °C to yield a mixture of two alkenes, C 10H 16. The major alkene B, gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Which of the following reactions are correct.
Reaction of HBr with 2-methylpropene yields 2-bromo-2-methylpropane. What is the structure of the carbocation formed during the reaction? Show the mechanism of the reaction.
Based on what you know about the relative stabilities of alkyl radicals and benzylic radicals, predict the product of addition of HBr to 1-phenylpropene in the presence of a free-radical initiator. Propose a mechanism for this reaction.
For each reaction, give the expected substitution product and predict whether the mechanism will be first order (SN1) or second order (SN2): a) 2-chloro-2-methylbutane + CH3COOH b) isobutyl bromide + NaOMe c) 1-iodo-1-methylcyclohexane + CH3CH2OH Q3. 2-Bromopentane, when treated with ‎ alcoholic KOH yields a mixture of three alkenes A, B and C. Identify A, B and C. Which is predominant?
1. Predict the elimination products of the following reactions. When two alkenes are possible, predict which one will be the major product. Explain your answers, showing the degree of substitution of each double bond in the products. 2. Which of these reactions are likely to produce both elimination and substitution products? (a) 2-bromopentane +NaOCH3 (b) 3-bromo-3-methylpentane +NaOMe(Me= methyl, CH3) (c) 2-bromo-3-ethylpentane +NaOH (d) cis-1-bromo-2-methylcyclohexane +NaOEt (Et= ethyl, CH2CH3)
3H. Put it all together. Predict the E1 products of the following reaction. Label alkenes as E/Z. 4. Predict the E1 products of the following reaction. Label akenes as E/Z.
Ozonolysis (O3 in CH2Cl2) of compound A under reducing conditions (Zn /acetic acid) gives formaldehyde, 2-butanone, and compound B. Catalytic hydrogenation (H2/Pd) of A gives 2,7-dimethylnonane. What is a possible structure for compound A? a. 2,7-Dimethyl-2,8-nonadieneb. 2,7-Dimethyl-1,8-nonadienec. 2,7-Dimethyl-1,6-nonadiened. 2,7-Dimethyl-1,7-nonadiene
Reaction of hbr with 2-methylpropene yields 2 bromo 2 methylpropane. What is the structure of the carbocation formed during the reaction? Show the mechanism of reaction.
Amines are converted into alkenes by a two-step process called Hofmann elimination. SN2 reaction of the amine with an excess of CH3I in the first step yields an intermediate that undergoes E2 reaction when treated with silver oxide as base. Pentylamine, for example, yields 1-pentene. Propose a structure for the intermediate, and explain why it readily undergoes elimination.
Acid-catalyzed hydrolysis of a 1, 2-epoxycyclohexane produces a transdiaxial 1, 2-diol. What product would you expect to obtain from acidic hydrolysis of cis-3-tert-butyl-l, 2-epoxycyclohexane? (Recall that the bulky tert-butyl group locks the cyclohexane ring into a specific conformation.)