Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 8.4, Problem 5P
Interpretation Introduction
Interpretation:
Using Markovnikov's rule, the major organic product formed in the reaction of hydrogen chloride with each of the given alkene is to be identified.
Concept introduction:
When an unsymmetrically substituted alkene is treated with a hydrogen chloride, a proton adds to the carbon that has the greater number of hydrogens, and chlorine adds to the carbon that has fewer number of hydrogens. This is Markovnikov's rule of addition.
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Write the structure of the major organic product obtained by hydroboration–oxidation of each
of the following alkenes:
(a) 2-Methylpropene (d) Cyclopentene
(b) cis-2-Butene (e) 3-Ethyl-2-pentene
Give the structure of the product formed when each of the following alkenes reacts with bromine in water: (a) 2-Methyl-1-butene (c) 3-Methyl-1-butene (b) 2-Methyl-2-butene (d) 1-Methylcyclopentene
Markovnikov’s rule is needed to predict the major product formed in the reaction between water and 2-butene.
Chapter 8 Solutions
Organic Chemistry - Standalone book
Ch. 8.1 - What three alkenes yield 2-methylbutane on...Ch. 8.2 - Prob. 2PCh. 8.2 - Prob. 3PCh. 8.3 - Prob. 4PCh. 8.4 - Prob. 5PCh. 8.4 - Give a structural formula for the carbocation...Ch. 8.5 - Prob. 7PCh. 8.6 - Instead of the three-step process of Mechanism...Ch. 8.6 - The rates of hydration of the two alkenes shown...Ch. 8.6 - Is the electrophilic addition of hydrogen chloride...
Ch. 8.7 - You can calculate the equilibrium constant for the...Ch. 8.7 - Does the presence or absence of a catalyst such as...Ch. 8.7 - The gas phase reaction of ethanol with hydrogen...Ch. 8.8 - Prob. 14PCh. 8.8 - Hydroborationoxidation of -pinene, like its...Ch. 8.10 - Arrange the compounds 2-methyl-1-butene,...Ch. 8.10 - Give the structure of the product formed when each...Ch. 8.11 - Prob. 18PCh. 8.11 - Prob. 19PCh. 8.12 - Prob. 20PCh. 8.12 - Prob. 21PCh. 8.13 - Prob. 22PCh. 8.14 - Prob. 23PCh. 8.14 - Prob. 24PCh. 8 - How many alkenes yield...Ch. 8 - Prob. 26PCh. 8 - Catalytic hydrogenation of...Ch. 8 - Prob. 28PCh. 8 - Prob. 29PCh. 8 - Prob. 30PCh. 8 - Prob. 31PCh. 8 - A single epoxide was isolated in 7984% yield in...Ch. 8 - Prob. 33PCh. 8 - Prob. 34PCh. 8 - On catalytic hydrogenation over a rhodium...Ch. 8 - Prob. 36PCh. 8 - Prob. 37PCh. 8 - Prob. 38PCh. 8 - Prob. 39PCh. 8 - 1-Butene has a higher heat of hydrogenation than...Ch. 8 - Match the following alkenes with the appropriate...Ch. 8 - The heats of reaction were measured for addition...Ch. 8 - Complete the following table by adding + and -...Ch. 8 - Match the heats of hydrogenation (107 kJ/mol,...Ch. 8 - The iodination of ethylene at 25 C is...Ch. 8 - Specify reagents suitable for converting...Ch. 8 - (a) Which primary alcohol of molecular formula...Ch. 8 - Identify compounds A and B in the retrosynthesis...Ch. 8 - Identify compounds A and B in the retrosynthesis...Ch. 8 - Prob. 50PCh. 8 - On being heated with a solution of sodium ethoxide...Ch. 8 - Compound A (C7H15Br) is not a primary alkyl...Ch. 8 - Prob. 53PCh. 8 - Prob. 54PCh. 8 - A mixture of three alkenes (A, B, and C) was...Ch. 8 - Reaction of 3,3-dimethyl-1-butene with hydrogen...Ch. 8 - Dehydration of 2,2,3,4,4-pentamethyl-3-pentanol...Ch. 8 - Prob. 58PCh. 8 - East Indian sandalwood oil contains a hydrocarbon...Ch. 8 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 62PCh. 8 - Prob. 63PCh. 8 - Prob. 64PCh. 8 - On the basis of the mechanism of acid-catalyzed...Ch. 8 - As a method for the preparation of alkenes, a...Ch. 8 - Which of the following is the most reasonable...Ch. 8 - Prob. 68PCh. 8 - Oxymercuration Concerns about mercurys toxicity...Ch. 8 - Prob. 70DSPCh. 8 - Prob. 71DSPCh. 8 - Prob. 72DSPCh. 8 - Prob. 73DSPCh. 8 - Oxymercuration Concerns about mercurys toxicity...
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- Write a structural formula for each of the following compounds. a. o-Ethylpropylbenzene b. m-Xylene c. 2-Bromotoluene d. 2-Phenylpropanearrow_forwardConsider the structure of cyclohexene, if it undergoes epoxidation followed by exposure to water, which of the following final product is formed? a. Cyclohexan-1,2,-diol b. Cyclohexane c. Cyclohexanone d. Hexan-1,-6-dioic acidarrow_forwardUsing condensed structural formulas, write a balanced chemical equation of each of the following reactions. Hydrogenation of cyclohexene Addition of H2O to trans-2-pentene using H2SO4 as a catalyst Reaction of 2-chloropropane with benzene in the presence of AlCl3.arrow_forward
- Remembering markovnikov’s rule, draw the structure of the carbocation formed during the reaction of 2-methylpropene with HCl.arrow_forwardThe addition of HCl to these compounds will follow Markovnikov’s rule EXCEPT a.1-pentene. b.1-butene. c.2-butene. d.propene.arrow_forwardwrite the reaction in which chlorine-2 butane is formed as a result of the action of one of the following compounds a) butene-1 with chlorine b) butene-1 with HCl c) butene-2 with chlorine d) butadiene-1,3 with HClarrow_forward
- Consider the structure of cyclohexene, if it undergoes strong oxidation, which of the following final product is formed? a. Cyclohexan-1,2,-diol b. Cyclohexane c. Cyclohexanone d. Hexan-1,-6-dioic acidarrow_forwardThe reaction of the organoborane intermediate in the anti-Markovnikov hydration of an alkene is said to be an oxidation. The hydration of alkenes is said to be a reduction. What does this mean in terms of the total number of electrons of the alkene reactantarrow_forwardMarkovnikov's rule can best be explained by considering * a) the number of hydrogen atoms attached to each of the double bond carbons atoms. b) the number of alkyl groups attached to each of the double bond carbons atoms. c) the relative stabilities of the carbocations that can be formed from the alkene. d) the spatial arrangement of the groups around the double bond. e) All of the above are good explanations for Markovnikov's rule.arrow_forward
- Find the molecular formula of the alkyne and then write down the corresponding reactions when it is known that from a molecule of propanol-1 a molecule of water is eliminated and then a molecule of hydrogen.arrow_forwardSupply the structural formula of the product in each of the following alkene addition reactions. a. CH3CH=CHCH3 + Cl2 ? b. CH3CHCH=CH2 + HCl ?arrow_forwardDescribe the following: Halogenation of Aromatic Compounds Alkylation of Organic Compounds Nitration of Organic Compoundsarrow_forward
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