9. The free radical bromination of cis-1,2,3-trimethylcyclopropane yields equal amounts of (S)- meso-3-methyl-2,4-dibromopentane and (dl)-3-methyl-2,4-dibromopentane as the sole reaction products. In contrast, bromination of trans-1,2,3-trimethylcyclopropane yields the same two products and a significant amount of (R)-meso-3-methyl-2,4- dibromopentane. Provide a detailed mechanistic analysis which accounts for the observed stereochemistry of the ring-opened dibromides.

9. The free radical bromination of cis-1,2,3-trimethylcyclopropane yields equal amounts of (S)- meso-3-methyl-2,4-dibromopentane and (dl)-3-methyl-2,4-dibromopentane as the sole reaction products. In contrast, bromination of trans-1,2,3-trimethylcyclopropane yields the same two products and a significant amount of (R)-meso-3-methyl-2,4- dibromopentane. Provide a detailed mechanistic analysis which accounts for the observed stereochemistry of the ring-opened dibromides.

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

Chapter6: Reactions Of Alkenes

Section: Chapter Questions

Problem 6.27P: Reaction of this bicycloalkene with bromine in carbon tetrachloride gives a trans dibromide. In both...

See similar textbooks

Similar questions

1)Chemistry students are taking an experimental course in organic chemistry at a public university. During an experiment involving conjugated dienes, some doubts arose when discussing the results obtained so far: (a) A student obtained two products from the reaction of 1,3-cyclohexadiene with Br2. His lab partner was surprised to get only one product from the reaction of 1,3 - cyclohexadiene with HBr. Explain these distinct results. (b) One student, seeing the discussion of colleagues, commented that she obtained two distinct products when reacting 1,3,5-hexatriene with HBr, with different yields just by changing the reaction temperature. Explain the results she obtained using reaction mechanism and based on kinetic and thermodynamic control involving conjugated dienes.
Please state which is the main product when 2-methylbuta-1,3-diene reacts with one equivalent of HBr for a limited time below 0 °C?
reaction of either 3-bromo-1-butene or (Z) -1-bromo-2-butene with water under SN1 condition yields the same product explain why
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.
Draw the structure of the conjugated diene that will react with one equivalent of HBr to yield a racemic mixture of 3-bromocyclohexene.
Show stereo chemistry and possible outcomes and the steps for the reaction.
How many possible monoborminated products including stereoisomers would you expect for the reaction of 2,3-dimethylpentane with Br2 in the presence of light? (4,6,5,7)?
In the reaction below, 3-Buten-2-one reacts with 2,3-Dimethyl-1,3-butadieneand 1,3-Butadieneat 140°C and 30°C, respectively. Explain why these two dienes react at different temperatures.
Reaction of this bicycloalkene with bromine in carbon tetrachloride gives a trans dibromide. In both (a) and (b), the bromine atoms are trans to each other. However, only one of these products is formed. Which trans dibromide is formed? How do you account for the fact that it is formed to the exclusion of the other trans dibromide?
Draw and name all stereoisomers of 3-chlorohepta-2,4-diene using the E-Z nomenclature.
draw the expected transition state for the reaction of trans,trans -1,4 diphenyl butadiene with maleic anhydride using the endo rule and predict the stereochemistry of the major qnd minor products from the reaction. help me to draw this..
1-Chloro-1,2-diphenylethane can undergo E2 elimination to give either cis- or trans-1,2-diphenylethylene (stilbene). Draw Newman projections of the reactive conformations leading to both possible products, and suggest a reason why the trans alkene is the major product.