EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 6, Problem 70P
a. Draw the product or products that will be obtained from the reaction of cis-2-butene and trans-2-butene with each of the following reagents. If a product can exist as stereoisomers, show which stereoisomers are formed.
- 1. HCl
- 2. BH3/THF, followed by HO–, H2O2, H2O
- 3. a peroxyacid
- 4. Br2 in CH2Cl2
- 5. Br2 + H2O
- 6. H2 + Pd/C
- 7. H2O + H2SO4
- 8. CH3OH + H2SO4
b. With which reagents do the two
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A. REACTIONS OF ALKENES- provide the product(s) or reagents that are needed
to accomplish the following transformations
CH3
1. BH 3, THF
2. H₂O₂, NaOH, H₂O
. Which of the following can be both formed from bromoethane and converted directly into ethanal? CH3CH2Br → X → CH3CHO
a. CH3CH2OH
b. CH3OCH3
c. CH3COOH
d. H2C=CHBr
Draw the product(s) of the following reactions.
CH3
H₂C-C-CEC-H
OH
1. BH3/THF
2. H₂O₂/ aqueous NaOH
• You do not have to consider stereochemistry.
Separate multiple products using the + sign from the drop-down menu.
• You do not have to explicitly draw H atoms.
• If no reaction occurs, draw the organic starting material.
Chapter 6 Solutions
EBK ORGANIC CHEMISTRY
Ch. 6.1 - Draw the mechanism for the reaction of cyclohexene...Ch. 6.2 - a. How many bond orbitals are avilable for...Ch. 6.2 - Prob. 3PCh. 6.2 - Prob. 4PCh. 6.3 - Prob. 5PCh. 6.4 - Prob. 6PCh. 6.4 - Prob. 7PCh. 6.4 - What alkene should be used to synthesize each of...Ch. 6.5 - The pKa of a protonated alcohol is about 2.5, and...Ch. 6.5 - Prob. 10P
Ch. 6.5 - Prob. 11PCh. 6.6 - a. What is the major product or each or the...Ch. 6.6 - Prob. 14PCh. 6.6 - Prob. 15PCh. 6.7 - What is the major product obtained from the...Ch. 6.8 - Which is more highly regionselective: reaction of...Ch. 6.8 - Prob. 19PCh. 6.9 - What will be the product of the preceding reaction...Ch. 6.9 - Prob. 21PCh. 6.9 - Prob. 22PCh. 6.9 - Prob. 23PCh. 6.9 - What is the product of the addition of 1Cl to...Ch. 6.9 - What will be the major product obtained from the...Ch. 6.9 - Propose a mechanism for the following reaction:Ch. 6.10 - Draw structures for the following: a. 24...Ch. 6.10 - What alkene would you treat with a peroxyacid in...Ch. 6.11 - What products are formed when the following...Ch. 6.11 - Prob. 31PCh. 6.11 - Prob. 32PCh. 6.11 - The following product was obtained from the...Ch. 6.12 - What characteristics must the reactant of a...Ch. 6.13 - Prob. 36PCh. 6.13 - What stereoisomers are obtained from each of the...Ch. 6.13 - Prob. 41PCh. 6.13 - Prob. 42PCh. 6.13 - Prob. 43PCh. 6.13 - Prob. 45PCh. 6.13 - Prob. 46PCh. 6.13 - Prob. 47PCh. 6.13 - Prob. 48PCh. 6.13 - Prob. 49PCh. 6.13 - Prob. 50PCh. 6.14 - Prob. 51PCh. 6.16 - Prob. 53PCh. 6.16 - Explain why 3-methykyclohexene should not be used...Ch. 6 - Prob. 55PCh. 6 - Prob. 56PCh. 6 - Prob. 57PCh. 6 - What is the major product of the reaction of...Ch. 6 - Give two names for each of the following:Ch. 6 - Prob. 60PCh. 6 - What are the products of the following reactions?...Ch. 6 - When 3-methyl-1-butene reacts with HBr, two alkyl...Ch. 6 - Draw curved arrows to show the flow of electrons...Ch. 6 - What reagents are needed to carry out the...Ch. 6 - Prob. 65PCh. 6 - Prob. 66PCh. 6 - Prob. 67PCh. 6 - What is more stable? a. CH3C+HCH3orCH3C+HCH2ClCh. 6 - Prob. 69PCh. 6 - a. Draw the product or products that will be...Ch. 6 - Prob. 71PCh. 6 - The second-order rate constant (in units of M1s1)...Ch. 6 - Which compound has the greater dipole moment?Ch. 6 - Prob. 74PCh. 6 - Prob. 75PCh. 6 - Prob. 76PCh. 6 - Prob. 77PCh. 6 - Prob. 78PCh. 6 - Prob. 79PCh. 6 - Prob. 80PCh. 6 - Prob. 81PCh. 6 - Prob. 82PCh. 6 - Prob. 83PCh. 6 - Prob. 84PCh. 6 - Prob. 85PCh. 6 - Prob. 86PCh. 6 - Draw the products of the following reactions. If...Ch. 6 - Prob. 88PCh. 6 - Prob. 89PCh. 6 - Prob. 90PCh. 6 - Two chemists at Dupont found that lCH2Znl is...Ch. 6 - Prob. 92PCh. 6 - Prob. 93PCh. 6 - What alkene gives the product shown after...Ch. 6 - Prob. 95PCh. 6 - Prob. 96PCh. 6 - Prob. 97PCh. 6 - Prob. 98PCh. 6 - Prob. 99PCh. 6 - Prob. 100PCh. 6 - Propose a mechanism for the following reaction:Ch. 6 - Prob. 102PCh. 6 - Prob. 103P
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- Draw the product(s) of the following reactions. 1. BH3 / THF 2. H₂O₂/aqueous NaOH H3C-CEC-H • You do not have to consider stereochemistry. • Separate multiple products using the + sign from the drop-down menu. • You do not have to explicitly draw H atoms. • If no reaction occurs, draw the organic starting material.arrow_forward5.Synthesis. Make the following products from a suitable cyclic alkene starting material. Look at the functional group PATTERN present in the molecule, including stereochemistry. Br CH 3 Br CH3arrow_forward43. Identify the reagent that will produce the following brominated product in greatest amount. Br A. Br2/uv B. Br2/FeBr3 C. NBS D. B12/CC14 44. Under acidic condition, which of the following compounds can not be oxidized by KMnO4. A. toluene B. 2-butene C. methylcyclohexane D. 2-butyne 45. What alkene product can be produced from the reaction of 2-hexyne with Lindlar's catalyst? A. cis-2-Hexene B. trans-2-Hexene C. Hexane D. A and Barrow_forward
- 1. What is it's type of reaction (Sn1, Sn2, E1, E2, Nucleophilic Addition, Nucleophilic Acyl Substition or Redox reaction). 2.What is it's major product.arrow_forwardCH3 CH3 Br- Br2 .CH3 CH2Cl2 CH3 H3C H3C Br Electrophilic addition of bromine, Brɔ, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl,. In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 CH3 CH3 CH3 H3C H3C :Br: :Br:arrow_forward2. Name each alkyne. a. CH3CH₂CH₂C=CH b. CH3CH₂CH₂C=CCH3 3. Predict the product of the following reactions. a. CH = CCH3 + HCI b. CH CCH₂CH3 + O2arrow_forward
- Draw the major organic product formed by reaction of 2-hexyne with the following reagent: H₂O in H₂SO4 / HgSO4. • Consider E/Z stereochemistry of alkenes. • In cases where there is more than one answer, just draw one. • If no reaction occurs, draw the organic starting material.arrow_forwardDraw the alkene that would react with the reagent given to account for the product formed. ? + + H₂O **** H₂S04 • 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. CH3 CH3 CHCCH3 | | OH CH3 +1arrow_forwardBr2 ? How many moles of Br are required to completely halogenate the alkene? A. Three moles B. Four moles C. Two moles D. One mole What is the expected arrangement of the bromine atoms relative to each other among the carbon involved in pi bonding? A. trans-configuration B. anti-conformation C. cis-configuration D. syn-conformation What happens to bromine when it is adjacent to an alkene during a chemical reaction? A. Bromine becomes polarized. B. Bromine becomes acidic. C. Bromine becomes hybridized. D. Bromine becomes stable. The relative arrangement of bromine atoms in the product is primarily due to: A. Hydrogen bonding B. Electronegativity C. Atomic weight D. Repulsion What is your observation after the reaction? A. Bromine water decolorizes. B. A brown precipitate forms. C. The alkene becomes denser. D. A yellow flame is produced.arrow_forward
- 1. RCOOOH 2. CgHgMgBr 3. Mild H30* 4. H2CRO4 5. CgHgMgBr 6. H3O*, heat Work through the synthesis on a separate sheet of paper, and then draw the structure of the final organic product. • You do not have to consider stereochemistry. • Do not draw organic or inorganic by-products. opy aste C. CH3 -CH3 ČH3 49%arrow_forwardWhat reagent (reactant) could be used to produce the product above from 1-butene? A. HBr B. Br2 C. OBR D. more than one of the above is correctarrow_forwardWhat about the second step in the electrophilic addition of HCl to an alkene-the reaction of chloride ion with the carbocation intermediate? Is this step exergonic or endergonic? Does the transition state for this second step resemble the reactant (carbocation) or the product (alkyl chloride)? Make a rough diagram of what the transition state may look like?arrow_forward
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