Concept explainers
(a)
Interpretation:
Newman projections must be utilized to explain why trans-stilbene is the major product when (S)-1-bromo-1,2-diphenylethane is used.
Concept Introduction :
During the elimination reaction, anti-periplanar groups are removed to form a double bond. Newman projection is the representation of a molecule when it is viewed through a particular bond between two atoms.
(b)
Interpretation:
Newman projections must be utilized to explain why trans-stilbene is the major product when (R)-1-bromo-1,2-diphenylethane is employed.
Concept Introduction :
During the elimination reaction, anti-periplanar groups are removed to form a double bond. Newman projection is the representation of a molecule when it is viewed through a particular bond between two atoms.
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Chapter 7 Solutions
ORGANIC CHEMISTRY
- Draw the products of the following reactions. If the products can exist as stereoisomers show what stereoisomers are formed. a. cis-2-pentene + Br2/CH2Cl2 b. trans-2-pentene + Br2/CH2Cl2 c. 1- butene + HCl d. methylcyclohexene + HBr e. trans-3-hexene + Br2/CH2Cl2 f. cis-3-hexene + Br2/CH2Cl2 g. 3,3-dimethyl-1-pentene + HBr h. cis-2-butene + HBr i. (Z)-2,3-dichloro-2-butene + H2, Pd/C j. (E)-2,3-dichloro-2-butene + H2, Pd/C k. (Z)-3,4-dimethyl-3-hexene + H2, Pd/C l. (E)-3,4-dimethyl-3-hexene + H2, Pd/Carrow_forward10. A compound X of molecular formula C8H12 with no triple bonds reacts with one equivalent of H2 to give a new compound having molecular formula CaH14. What can be inferred about the structure of compound X? A) Compound X has 3 rings. B) Compound X has 3 pi bonds. Compound X has 1 ring and 2 pi bonds. D) Compound X has 2 rings and 1 pi bond. 11. Determine the product of the following reaction. H, Lindlar's cat. %3D IV A)I B) II C) III D) IV Type here to search 互i | A C 三Darrow_forwarda. Identify two alkenes that react with HBr to form 1-bromo-1-methylcyclohexane without undergoing a carbocation rearrangement. b. Would both alkenes form the same alkyl halide if DBr were used instead of HBr? (D is an isotope of H, so D+ reacts like H+.)arrow_forward
- Draw the structure of the major organic product of the reaction below. CH3 CH₂CHCH₂CH₂CH=CH₂ + CHC13 KOH • Use the wedge/hash bond tools to indicate stereochemistry where it exists. Show stereochemistry in a meso compound. If the reaction produces a racemic mixture, just draw one stereoisomer.arrow_forward3. Draw the structures of the products, showing stereochemistry where relevant. a) 1-methylcyclohexene HBr b) Br2 1-methylcyclohexene Br2 1-methylcyclohexene → H2O 4. When bromine adds to the double bond in cyclohexene, the resulting dibromide is trans. This stereochemistry is due to: a) The intermediate bromonium ion d) Markovnikov's rule b) the intermediate carbocation d) IUPAC rulesarrow_forward10. Draw ALL possible stereoisomers possible for 8i. Give the configurations of each stereocenter in 8i. (NOTE: Ph is the abbreviation for an aromatic ring and is assigned a priority of 4 in the structure for 8i, below) H₂C U CH3 MAIII OH Product 8iarrow_forward
- + Draw one of the two stereoisomers of the major product from this reaction. Use a dash or wedge bond to indicate stereochemistry of substituents on asymmetric centers. Ignore inorganic byproducts. 1. BH 3-THF 2. H2O2, NaOH Qarrow_forward15. Which of the following carbocations is the most stable? a) ethyl carbocation, CH3CH2+ b) rpropyl carbocation, CH3CH2CH2* c) Isopropyl carbocation, (CH3)2CH* d) t-butyl carbocation, (CH3)3C+arrow_forwardDraw one of the two stereoisomers of the major product from this reaction. Use a dash or wedge bond to indicate the stereochemistry of substituents on asymmetric centers. Ignore inorganic byproducts. C 1. BH3-THF 2. H2O2, NaOHarrow_forward
- Draw a structural formula for the substitution product of the reaction shown below. ● H3C- ● H3C H Br + Na OCCH3 DMF • Use the wedge/hash bond tools to indicate stereochemistry where it exists. If more than one stereoisomer of product is formed, draw both. Separate multiple products using the + sign from the drop-down menu. Products that are initially formed as ions should be drawn in their neutral forms. DMF = dimethylformamidearrow_forward1A. What is the trend for carbocation stability? 1B. In the reaction of 2-hexene with HBr, which of the products is expected to be formed in a larger amount. Explain your answer. 1C. Why do carbocation rearrangements occur?arrow_forward1% mol Pd(OAc)2 4% mol Ph3P B с CH3CN A (1 ring) (2 rings) (3 rings) The above reaction involves two sequential Heck reactions and three organopalladium intermediates. In the box below draw the structure of intermediate C. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Use R1 for the PdL₂I group. The R group tool is located in the charges and lone pairs drop-down menu. Sn [F ?arrow_forward
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