O. Reaction of HBr with 3-methylcyclohexene yields a mixture of four products: cis- and trans-1-bromo-3-methylcyclohexane and cis- and trans-1-bromo-2- methylcyclohexane. The analogous reaction of HBr with 3-bromocyclohexene yields trans-1,2-dibromocyclohexane as the sole product. Draw structures of the possible intermediates, and then explain why only a single product is formed in this reaction.

O. Reaction of HBr with 3-methylcyclohexene yields a mixture of four products: cis- and trans-1-bromo-3-methylcyclohexane and cis- and trans-1-bromo-2- methylcyclohexane. The analogous reaction of HBr with 3-bromocyclohexene yields trans-1,2-dibromocyclohexane as the sole product. Draw structures of the possible intermediates, and then explain why only a single product is formed in this reaction.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter14: Conjugated Compounds And Ultraviolet Spectroscopy

Section14.SE: Something Extra

Problem 54AP

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Reaction of HBr with 3-methylcyclohexene yields a mixture of four products: cis-and trans-1-bromo-3-methylcyclohexane and cis-and trans-1-bromo-2-methylcyclohexane. The analogous reaction of HBr with 3-bromocyclohexene yields trans-1, 2-dibromocyclohexane as the soleproduct. Draw structures of the possible intermediates, and then explain why only a single product is formed in this reaction.
What stereoisomers are obtained from the following reactions? a. 1-butene + H2O + H2SO4 b. cyclohexene + HBr c. cis-3-heptene + Br2 d. trans-3-hexene + Br2
Give the structure corresponding to each name.a. 3-bromo-4-ethylheptaneb. 1,1-dichloro-2-methylcyclohexanec. 1-bromo-4-ethyl-3-uorooctaned. (S)-3-iodo-2-methylnonanee. (1R,2R)-trans-1-bromo-2-chlorocyclohexanef. (R)-4,4,5-trichloro-3,3-dimethyldecane
CH3 CH3 CH3 CH;=ĊCH,CHCH;OH H2SO4, H3C H3C Referring to the above reaction: 1. Which atom does the H2SO4 first remove? 2. Identify the reaction if it's hydrogenation, hydrohalogenation, etc. 3. Propose a mechanism for the reaction, using the arrow formalism to indicate the flow of electrons.
Classify the following substituents according to whether they are electron donors or electron acceptors relative to hydrogen by the resonance and the inductive mechanisms. 1. -CI: chloro 3. Inductive effect 2. -CH₂CH₂CH3C=CH Inductive effect :0: || —CH,CH,CH,CH=CH-C—CCH3 Resonance effect Resonance effect Inductive effect Resonance effect
b. Increasing reactivity with HBr H3C Н H3C A Н least reactive н н Н В I H3C Н C I н н Н D CH₂CH3 most reactive
Dehydrohalogenation of 1-chloro-1-methylcyclopropane affords two alkenes (A and B) as products. Explain why A is the major product despite the fact that it contains the less substituted double bond.
Compounds X and Y are both C5H11CI products formed in the radical chlorination of pentane. Base-promoted E2 elimination of X and Y gives, in each case, a single C5H10 alkene (ignoring double bond stereochemistry). Both X and Y react in SN2 fashion with sodium iodide in acetone; Y reacts faster than X. What is the structure of Y? • 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. ChemDoodle (Previous Next
Which stereoisomer of 3-hexene forms (3S,4S)-4-bromo-3-hexanol and (3R,4R)-4-bromo-3-hexanol when it reacts with Br2 and H2O?
cis-1-Bromo-4-tert-butylcyclohexane and trans-1-bromo-4-tert-butylcyclohexane both react with sodium ethoxide in ethanol to form 4-tert-butylcyclohexene. Explain why the cis isomer reacts much more rapidly than the trans isomer.
1. Illustrate details mechanism of reactions for bromination of the following alkane. State each of the steps involves. CH3 Br2 CH `CH3 hv, 25°C H3C 2. Draw the two chair conformations of cis-1-chloro-4-methylcyclohexane. Which of the conformers is more stable?
A chemist allows some pure (2S,3R)-3-bromo-2,3-diphenylpentane to react with a solution of sodium ethoxide(NaOCH2 CH3) in ethanol. The products are two alkenes: A (cis-trans mixture) and B, a single pure isomer. Under the same conditions, the reaction of (2S,3S)-3-bromo-2,3-diphenylpentane gives two alkenes, A (cis-trans mixture) and C. Upon catalytic hydrogenation, all three of these alkenes (A, B, and C) give 2,3-diphenylpentane. Determine the structures of A, B, and C; give equations for their formation; and explain the stereospecificity of these reactions.