(a)
Interpretation:
The principal organic compound that is expected when
Concept introduction:
The addition reaction of the
Answer to Problem 17.23AP
The principal organic compound that is formed when
Explanation of Solution
The reaction of
Figure 1
The addition of the bromine molecule on the double bond of the alkene takes place to give the dibromo product. The addition of bromine to the double bond is the anti-addition.
The principal organic compound that is formed when
(b)
Interpretation:
The principal organic compound that is expected when
Concept introduction:
The addition reactions of the alkene are very well known reactions. The electron density on the alkene double bond makes it nucleophilic. The alkene undergoes varieties of addition reaction via different mechanisms.
Answer to Problem 17.23AP
The principal organic compound that is formed when
Explanation of Solution
The reaction of
Figure 2
The reaction of an alkene with N-bromosuccinimide in the presence is the free-radical reaction. In this reaction, allylic bromination is observed instead of an addition to the alkene. The N-bromosuccinimide acts as radical initiator. This molecule breaks the
The principal organic compound that is formed when
(c)
Interpretation:
The principal organic compound that is expected when product(s) of part (b) undergo solvolysis in aqueous acetone is to be stated.
Concept introduction:
The nucleophilic substitution reactions are the reactions in which a nucleophile attacks at the electrophilic carbon and eliminates another group. The
The
Answer to Problem 17.23AP
The principal organic compounds that are formed when product(s) of part (b) undergo solvolysis in aqueous acetone are shown below.
Explanation of Solution
The products of part (b) are shown below.
Figure 3
The reaction of product(s) of part (b) on solvolysis in aqueous acetone is shown below.
Figure 4
The nucleophilic substitution reaction takes place when solvolysis of products of part (b) is done. The bromine group is substituted by the hydroxyl group giving rise to the formation of an allylic alcohol.
The principal organic compound that is formed when product(s) of part (b) undergo solvolysis in aqueous acetone is shown in Figure 4.
(d)
Interpretation:
The principal organic compound that is expected when product(s) of part (b) are reacted with
Concept introduction:
The reaction of an
Answer to Problem 17.23AP
The principal organic compounds that are formed when product(s) of part (b) are reacted with
Explanation of Solution
The products of part (b) are shown below.
Figure 3
The reaction that occurs when product(s) of part (b) are reacted with
Figure 5
The allylic halide also undergoes the same kind of reactions as the alkyl halide with magnesium metal in dry ether. They also lead to the formation of Grignard reagent but this time with the allylic group.
The principal organic compounds that are formed when product(s) of part (b) are reacted with
(e)
Interpretation:
The principal organic compound that is expected when product(s) of part (d) are reacted with
Concept introduction:
The nucleophilic substitution reactions are the reactions in which a nucleophile attacks at the electrophilic carbon and eliminates another group. The rate of reaction depends upon the nucleophilicity and concentration of the nucleophile.
The
Answer to Problem 17.23AP
The principal organic compounds that are formed when product(s) of part (d) are reacted with
Explanation of Solution
The products of part (d) are shown below.
Figure 6
The reaction of product(s) of part (d) with
Figure 7
The Grignard reagents are highly reactive towards moisture. The carbon chain on the Grignard reagent gets the hydrogen in place of
The principal organic compounds that are formed when product(s) of part (d) are reacted with
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Chapter 17 Solutions
Organic Chemistry Study Guide and Solutions
- A problem often encountered in the oxidation of primary alcohols to acids is that esters are sometimes produced as by-products. For example, oxidation of ethanol yields acetic acid and ethyl acetate: Propose a mechanism to account for the formation of ethyl acetate. Take into account the reversible reaction between aldehydes and alcohols:arrow_forwardWhen tert-butyl bromide is heated with an equal amount of ethanol in an inert solvent, one of the products is ethyl tert-butyl ether. (a) What happens to the reaction rate if the concentration of ethanol is doubled?arrow_forwardProvide the missing reagents to complete the reactions below, if there is more than one step required, be sure to indicate appropriately.arrow_forward
- Two products are possible when pent-2-ene is treated with HBr. Write the structures of the possible products, and explain why they are made in about equal amounts.arrow_forwardPredict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.(a) ethanoarrow_forwardWhen bromomethane undergoes solvolysis in a solvent mixture composed of 90% water/10% acetone, the reaction rate is faster than when the same compound is solvolyzed in 80% water/20% acetone. Explain.arrow_forward
- Starting with benzene and using any other necessary reagents of your choice, create a synthesis (or sytheses) for each of the following compounds.arrow_forwardDiphenylacetylene can be synthesized by the double dehydrohalogenation of 1,2-dibromo-1,2-diphenylethene. The sequence starting from (E)-1,2-diphenylethene consists of bromination to give the dibromide, followed by dehydrohalogenation to give a vinylic bromide, then a second dehydrohalogenation to give diphenylacetylene.(a) What is the structure, including stereochemistry, of the vinylic bromide?(b) If the sequence starts with (Z)-1,2-dibromo-1,2-diphenylethene, what is (are) the structure(s) of the intermediate dibromide(s)? What is the structure of the vinylic bromide?arrow_forwardThe compound eutypine is an antibacterial agent isolated from the fungus Eutypa lata. This fungus results in a disease common to vineyards called eutyposis. Give a sequence of reactions that will take the following reactant and give eutypine when the other reactants used in the sequence are acetylene and acetone.arrow_forward
- Compounds X and Y are both C7H15Cl products formed in the radical chlorination of 2,4-dimethylpentane. Base-promoted E2 elimination of X and Y gives, in each case, a single C7H₁4 alkene. Both X and Y undergo an SN2 reaction with sodium iodide in acetone solution to give C7H15l products; in this reaction Y reacts faster than X. What is the structure of X? • Do not use stereobonds in your answer. • In cases where there is more than one possible structure for each molecule, just give one for each. . Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. наarrow_forwardWhen 2-iodo-1,4-dimethylcyclohexane is heated in acetic acid, CH3COOH, a mixture of substitution and elimination products is obtained. Provide structures for all possible products, writing [not drawing] the name of the mechanism by which each one is formed.arrow_forwardTreatment of a hydrocarbon A (molecular formula C9H18) with Br2 in the presence of light forms alkyl halides B and C, both having molecular formula C9H17Br. Reaction of either B or C with KOC(CH3)3 forms compound D (C9H16) as the major product. Ozonolysis of D forms cyclohexanone and acetone. Identify the structures of A–D.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning