
Concept explainers
Interpretation:
The structures of the major organic products formed in the reaction of
Concept introduction:
When an unsymmetrically substituted alkene reacts with a hydrogen halide, the hydrogen adds to the carbon that has the greater number of hydrogens, and the halogen adds to the carbon that has fewer hydrogens. This rule is called Markovnikov’s rule.
During hydroboration oxidation, hydrogen forms a bond with the carbon atom that has fewer hydrogens attached to it and the hydroxyl atom forms a bond with the carbon atom that has a greater number of hydrogens attached to it. This is a rule opposite to the Markovnikov’s addition.

Answer to Problem 28P
Solution:
Explanation of Solution
(a) Reaction of
The given alkene,
Hydrogen chloride gets added to the double bond of
(b) Reaction of
This reaction is an acid catalyzed electrophilic addition reaction of alkenes in which water molecule adds to the double bond in
A molecule of water adds to the double bond of
The addition mechanism for this reaction follows the Markovnikov’s rule. Therefore, the major organic product for the above acid-catalyzed electrophilic addition reaction is
(c) Reaction of
Hydroboration-oxidation leads to the overall hydration of an alkene. In hydroboration-oxidation,
The hydrogen atom in the water molecule adds to the carbon
In case of
(d) Reaction of
Bromine reacts rapidly with alkenes by electrophilic addition. The products are called vicinal dibromides, meaning that the bromine atoms get attached to adjacent double bonded carbon atoms. It is carried out in suitable solvents like
A molecule of bromine adds across the double bond in
(e) Reaction of
Chlorine and bromine react with alkenes in aqueous solution to give the corresponding vicinal halohydrins – compounds that add a halogen and hydroxyl group on adjacent carbon atoms in the alkene. The halogen atom forms a bond with that carbon atom in alkene, which has a greater number of hydrogen atoms, while the hydroxyl group bonds to that carbon atom in alkene, which has a fewer number of hydrogen atoms.
In the reaction of
(f) Reaction of
Peroxyacid transfers oxygen to the double bond of alkene to yield epoxides, which is a three-membered oxygen-containing ring.
When
(g) Reaction of
Ozone is a powerful electrophile and reacts with alkenes to cleave the double bond between two oxygen atoms in the molecule, forming an ozonide.
When
(h) Product of part (g) treated with zinc in water
Ozonides are formed as a result of the reaction of ozone with an alkene. Ozonides undergo hydrolysis in water giving carbonyl compounds. Depending upon the structure of the starting alkene, various carbonyl compounds such as formaldehyde, aldehydes, or ketones are formed.
When corresponding ozonide of
(i) Product of part (g) is treated with dimethyl sulfide.
Ozonides are formed as a result of the reaction of ozone with an alkene. Ozonides undergo hydrolysis in water, giving carbonyl compounds. Depending upon the structure of the starting alkene, various carbonyl compounds such as formaldehyde, aldehydes, or ketones are formed.
When corresponding ozonide of
Want to see more full solutions like this?
Chapter 8 Solutions
ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
- (a) Write down the structure of EDTA molecule and show the complex structure with Pb2+ . (b) When do you need to perform back titration? (c) Ni2+ can be analyzed by a back titration using standard Zn2+ at pH 5.5 with xylenol orange indicator. A solution containing 25.00 mL of Ni2+ in dilute HCl is treated with 25.00 mL of 0.05283 M Na2EDTA. The solution is neutralized with NaOH, and the pH is adjusted to 5.5 with acetate buffer. The solution turns yellow when a few drops of indicator are added. Titration with 0.02299 M Zn2+ requires 17.61 mL to reach the red end point. What is the molarity of Ni2+ in the unknown?arrow_forwardA compound has the molecular formula CH40, and shows a strong IR absorption at 2850-3150 cm. The following signals appear in the 'H NMR spectrum: 1.4 ppm (triplet, 6H), 4.0 ppm (quartet, 4H), 6.8 ppm (broad singlet, 4H). Which of the following structures is consistent with these data? Select the single best answer. OCH CH₂ x OCH2CH3 CH₂OCH3 OH CH₂OCH OH CH, OCH₁ CH₂OCH, CH₂OCH HO OH ° CH₂OCH3arrow_forwardpredict the major product while showing me the intermidiate products from each reagent/reagent grouparrow_forward
- Why is it desirable in the method of standard addition to add a small volume of concentrated standard rather than a large volume of dilute standard? An unknown sample of Cu2+ gave an absorbance of 0.262 in an atomic absorption analysis. Then 1.00 mL of solution containing 100.0 ppm (= µg/mL) Cu2+ was mixed with 95.0 mL of unknown, and the mixture was diluted to 100.0 mL in a volumetric flask. The absorbance of the new solution was 0.500. Calculate the concentration of copper ion in the sample.arrow_forwardWhat is the relation between the standard deviation and the precision of a procedure? What is the relation between standard deviation and accuracy? The percentage of an additive in gasoline was measured six times with the following results: 0.13, 0.12, 0.16, 0.17, 0.20, 0.11%. Find the 90% and 99% confidence intervals for the percentage of the additive.arrow_forwardIf you measure a quantity four times and the standard deviation is 1.0% of the average, can you be 90% confident that the true value is within 1.2% of the measured average?arrow_forward
- Write down three most common errors in thermogravimetric analysis. Identify them as systematic or random errors and discuss how you can minimize the errors for better results.arrow_forwarda) A favorable entropy change occurs when ΔS is positive. Does the order of the system increase or decrease when ΔS is positive? (b) A favorable enthalpy change occurs when ΔH is negative. Does the system absorb heat or give off heat when ΔH is negative? (c) Write the relation between ΔG, ΔH, and ΔS. Use the results of parts (a) and (b) to state whether ΔG must be positive or negative for a spontaneous change. For the reaction, ΔG is 59.0 kJ/mol at 298.15 K. Find the value of K for the reaction.arrow_forwardA sample of hydrated magnesium sulfate (MgSO4⋅xH2O) is analyzed using thermogravimetric analysis (TGA). The sample weighs 2.50 g initially and is heated in a controlled atmosphere. As the temperature increases, the water of hydration is released in two stages: (a) The first mass loss of 0.72 g occurs at 150°C, corresponding to the loss of a certain number of water molecules. (b) The second mass loss of 0.90 g occurs at 250°C, corresponding to the loss of the remaining water molecules. The residue is identified as anhydrous magnesium sulfate (MgSO4) Questions: (i) Determine the value of x (the total number of water molecules in MgSO4⋅xH2O) (ii) Calculate the percentage of water in the original sample. Write down the applications of TGA.arrow_forward
- The solubility product of iron(III) hydroxide (Fe(OH)3) is 6.3×10−38. If 50 mL of a 0.001 M FeCl3 solution is mixed with 50 mL of a 0.005 M NaOH solution, will Fe(OH)3 precipitate? Show all step-by-step calculations. To evaluate the equilibrium constant, we must express concentrations of solutes in mol/L, gases in bars, and omit solids, liquids, and solvents. Explain why.arrow_forwardPredict the major products of this organic reaction.arrow_forward2. Provide the structure of the major organic product in the following reaction. Pay particular attention to the regio- and stereochemistry of your product. H3CO + H CN Aarrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY





