
Concept explainers
Devise a synthesis of each product from the given starting material. More than one step is required.
a. d.
b. e.
c. f.

(a)
Interpretation: The synthesis of each product from the given starting material having more than one step is to be predicted.
Concept introduction: The removal of two substituents from a molecule either in one step or in two steps is called an elimination reaction.
For preparation of alkenes, acid-catalyzed dehydration of alcohols is one of the best methods. Less substituted alkene is the minor product when a mixture of constitutional isomers is possible. The reaction occurs via E1 mechanism or by an E2 mechanism. For primary alcohols, the reaction involves E2 mechanism, whereas for secondary and tertiary alcohols, the reaction occurs via E1 mechanism.
Hydration of alkenes is one the method used for the formation of alcohol.
The general steps involved in the hydration reaction are stated below:
• First protonation of the alkene take place to generate the carbocation.
• Formation of protonated alcohol.
• Deprotonation.
Answer to Problem 10.64P
The synthesis of each product from the given starting material having more than one step is shown below.
Explanation of Solution
For preparation of alkenes, acid-catalyzed dehydration of alcohols is one of the best methods. Less substituted alkene is the minor product when a mixture of constitutional isomers is possible. The reaction occurs via E1 mechanism or by an E2 mechanism. For primary alcohols, the reaction involves E2 mechanism, whereas for secondary and tertiary alcohols, the reaction occurs via E1 mechanism.
The general steps involved in the hydration reaction are stated below:
• First protonation of the alkene take place to generate the carbocation.
• Formation of protonated alcohol.
• Deprotonation.
The given conversion is,
Figure 1
The above diagram shows the conversion of primary alcohol into secondary alcohol. The process involves two steps. The first step is the dehydration of alcohol that results in the formation of alkene. In the next step, hydration of alkene takes place to give secondary alcohol.
The reaction that shows the formation of secondary alcohol is shown below.
Figure 2
The synthesis of each product from the given starting material having more than one step is rightfully stated.

(b)
Interpretation: The synthesis of each product from the given starting material having more than one step is to be predicted.
Concept introduction: The removal of two substituents from a molecule either in one step or in two steps is called an elimination reaction.
In elimination reaction, abstraction of proton occurs to form an alkene. Elimination reactions are of two types that is
Hydroboration reaction is a two step reaction, which involves conversion of alkene into alcohol. This type of reaction follows anti-markovnikov’s rule.
Answer to Problem 10.64P
The synthesis of each product from the given starting material having more than one step is shown below.
Explanation of Solution
Hydroboration reaction is a two step reaction, which involves conversion of alkene into alcohol. This type of reaction follows anti-markovinokov’s rule.
Anti markovinokov’s rule states that the positive part of acid attached to that carbon atom in
The given conversion is,
Figure 3
The above diagram shows the conversion of
The reaction that shows the formation of
Figure 4
The synthesis of each product from the given starting material having more than one step is rightfully stated.

(c)
Interpretation: The synthesis of each product from the given starting material having more than one step is to be predicted.
Concept introduction: The removal of two substituents from a molecule either in one step or in two steps is called an elimination reaction. Dehydrohalogenation is the elimination of halogen that results in the formation of alkene.
The reaction of hydrogen halide with alkene results in the formation of alkyl halide. This type of reaction is an electrophilic addition of hydrogen halide.
Electrophilic addition reactions are those in which breaking of pi bond take place to form new sigma bond. In this type of reaction, carbocation is formed during the formation of new bond.
Answer to Problem 10.64P
The synthesis of each product from the given starting material having more than one step is shown below.
Explanation of Solution
The removal of two substituents from a molecule either in one step or in two steps is called an elimination reaction. Dehydrohalogenation is the elimination of halogen that results in the formation of alkene.
The reaction of hydrogen halide with alkene results in the formation of alkyl halide. This type of reaction is an electrophilic addition of hydrogen halide.
Electrophilic addition reactions are those in which breaking of pi bond take place to form new sigma bond. In this type of reaction, carbocation is formed during the formation of new bond.
The given conversion is,
Figure 5
The above diagram shows the conversion of
The reaction that shows the formation of
Figure 6
The synthesis of each product from the given starting material having more than one step is rightfully stated.

(d)
Interpretation: The synthesis of each product from the given starting material having more than one step is to be predicted.
Concept introduction: The general steps followed by the given reaction are as follows:
• Bromination of alkene.
• Reaction of dihalide product with soda amide to form alkyne product.
Answer to Problem 10.64P
The synthesis of each product from the given starting material having more than one step is shown below.
Explanation of Solution
The given conversion is,
Figure 7
The above diagram shows the conversion of allylcycohexane into
The reaction that shows the formation of alkyne is shown below.
Figure 8
The synthesis of each product from the given starting material having more than one step is rightfully stated.

(e)
Interpretation: The synthesis of each product from the given starting material having more than one step is to be predicted.
Concept introduction: The removal of two substituents from a molecule either in one step or in two steps is called an elimination reaction. Dehydrohalogenation is the elimination of halogen that results in the formation of alkene.
Bromination of alkene results in the formation of bromo products.
The reaction of dihalide reactant with soda amide results in the formation of alkyne product.
Answer to Problem 10.64P
The synthesis of each product from the given starting material having more than one step is shown below.
Explanation of Solution
The given conversion is,
Figure 9
The above diagram shows the conversion of
The reaction that shows the formation of alkyne is shown below.
Figure 10
The synthesis of each product from the given starting material having more than one step is rightfully stated.

(f)
Interpretation: The synthesis of each product from the given starting material having more than one step is to be predicted.
Concept introduction: The removal of two substituents from a molecule either in one step or in two steps is called an elimination reaction. Dehydrohalogenation is the elimination of halogen that results in the formation of alkene.
Answer to Problem 10.64P
The synthesis of each product from the given starting material having more than one step is shown below.
Explanation of Solution
The given conversion is,
Figure 11
The above diagram shows the conversion of
The reaction that shows the formation of alkyne is shown below.
Figure 12
The synthesis of each product from the given starting material having more than one step is rightfully stated.
Want to see more full solutions like this?
Chapter 10 Solutions
PKG ORGANIC CHEMISTRY
Additional Science Textbook Solutions
Laboratory Manual For Human Anatomy & Physiology
Human Physiology: An Integrated Approach (8th Edition)
Organic Chemistry (8th Edition)
Biochemistry: Concepts and Connections (2nd Edition)
Organic Chemistry
- 10. Write out the mechanism (intermediate/transition state) for this reaction; indicate stereochemistry in product. H3C CH₂OH CH3 SN1 Harrow_forwardWrite "most" under the member of each trio which is most stable. Write "least under the member of each trio which is least stable. b) Draw a Fischer projection of a pair of enantiomers with three chiral carbons. Which of these two would you expect to be more soluble in water? Why? 1-butanol 1-heptanol Which of these two would you expect to have the higher boiling point? Why? hexyl methyl ether 1-heptanolarrow_forwardWrite "most" under the most acidic compound. Write "least" under the least acidic compound. OH NO₂ OCH3 Br 9. Compound X, C50H84F2, reacts with excess H2/Pd to give a C50H88F2 compound. How many rings are in X? How many double bonds are in X? Show your work.arrow_forward
- 4. State whether these two are: a) the same molecule b) c) d) different compounds that are not isomers constitutional isomers diastereomers e) enantiomers CH3 CH₁₂ H OH HO H H OH HO H CH, CH₂ 5. a) How many stereocenters does this compound have? b) How many stereoisomers are possible for this compound? CH₂ OH CHCHarrow_forwardCalculating the pH at equivalence of a titration A chemist titrates 210.0 mL of a 0.1003 M hydrobromic acid (HBr) solution with 0.7550M KOH solution at 25 °C. Calculate the pH at equivalence. Round your answer to 2 decimal places. Note for advanced students: you may assume the total volume of the solution equals the initial volume plus the volume of KOH solution added. pH = ] ☑ o0o 18 Ararrow_forwardDo you do chemistry assignmentsarrow_forward
- Using the conditions of spontaneity to deduce the signs of AH and AS Use the observations about each chemical reaction in the table below to decide the sign (positive or negative) of the reaction enthalpy AH and reaction entropy AS. Note: if you have not been given enough information to decide a sign, select the "unknown" option. reaction observations conclusions A This reaction is always spontaneous, but proceeds slower at temperatures above 120. °C. ΔΗ is (pick one) AS is (pick one) ΔΗ is (pick one) B This reaction is spontaneous except above 117. °C. AS is (pick one) ΔΗ is (pick one) This reaction is slower below 20. °C than C above. AS is |(pick one) ? 18 Ar 1arrow_forwardCalculating the pH at equivalence of a titration Try Again Your answer is incorrect. 0/5 a A chemist titrates 70.0 mL of a 0.7089 M hydrocyanic acid (HCN) solution with 0.4574M KOH solution at 25 °C. Calculate the pH at equivalence. The pK of hydrocyanic acid is 9.21. Round your answer to 2 decimal places. Note for advanced students: you may assume the total volume of the solution equals the initial volume plus the volume of KOH solution added. pH = 11.43] G 00. 18 Ar B•arrow_forwardBiological Macromolecules Naming and drawing the products of aldose oxidation and reduction aw a Fischer projection of the molecule that would produce L-ribonic acid if it were subjected to mildly oxidizing reaction conditions. Click and drag to start drawing a structure. X AP ‡ 1/5 Naor Explanation Check McGraw Hill LLC. All Rights Reserved. Terms of Use Privacy Center Accessibilarrow_forward
- ● Biological Macromolecules Identifying the parts of a disaccharide Take a look at this molecule, and then answer the questions in the table below it. CH2OH O H H H OH OH OH H H CH2OH H O OH H OH H H H H OH Is this a reducing sugar? Does this molecule contain a glycosidic bond? If you said this molecule does contain a glycosidic bond, write the symbol describing it. If you said this molecule does contain a glycosidic bond, write the common names (including anomer and enantiomer labels) of the molecules that would be released if that bond were hydrolyzed. If there's more than one molecule, separate each name with a comma. Explanation Check O yes X O no ○ yes O no Uarrow_forwardThe aim of the lab is to measure the sodium content from tomato sauce using the Mohr titration method. There are two groups being: Regular Tomato sauce & Salt Reduced tomato sauce QUESTION: State how you would prepare both Regular & Salt reduced tomato sauce samples for chemical analysis using the Mohr titration methodarrow_forwardUsing the conditions of spontaneity to deduce the signs of AH and AS Use the observations about each chemical reaction in the table below to decide the sign (positive or negative) of the reaction enthalpy AH and reaction entropy AS. Note: if you have not been given enough information to decide a sign, select the "unknown" option. reaction observations conclusions A The reverse of this reaction is always spontaneous but proceeds faster at temperatures above -48. °C. ΔΗ is (pick one) ✓ AS is (pick one) B This reaction is spontaneous except below 114. °C but proceeds at a slower rate below 135. °C. ΔΗ is (pick one) AS is (pick one) ΔΗ is C This reaction is exothermic and proceeds faster at temperatures above -43. °C. (pick one) AS is (pick one) v Х 5 ? 18 Ararrow_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





