Concept explainers
(a)
Interpretation:
The principal organic compound that is expected when
Concept introduction:
The addition reaction of the
Answer to Problem 17.22AP
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 17.22AP
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 group is substituted by a nucleophile. The rate of reaction depends upon the nucleophilicity and concentration of the nucleophile.
The
Answer to Problem 17.22AP
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 when product(s) of part (b) undergo solvolysis in aqueous acetone is shown below.
Figure 4
The nucleophilic substitution reaction takes place when solvolysis of products of part (b) takes place. 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 17.22AP
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 are do the alkyl halide with magnesium metal in dry ether. They are also lead to the formation of Grignard reagent but this time with the allylic group.
The principal organic compound that is formed when product(s) of part (b) undergo solvolysis in aqueous acetone is shown in Figure 5.
(e)
Interpretation:
The principal organic compound that is expected when product(s) of part (d) are reacted with
Concept introduction:
The reaction of an alkyl halide with a metal-like magnesium in the presence of dry ether leads to the formation of
Answer to Problem 17.22AP
The principal organic compound that is formed when products of part (d) react with
Explanation of Solution
The products of part (d) are shown below.
Figure 6
The Gringnard reagents react with
Figure 7
The principal organic compound that is formed when products of part (d) react with
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Chapter 17 Solutions
Organic Chemistry
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- Predict the major product or the necessary reagent or reactant to complete each of the following reactions. In the box before each reaction, indicate the mechanism followed by the reaction. (Free radical (FR), SN2, SN1). (b) (a) Cl₂ CH₂CH₂OH (a) 1 hv 2 (b) H Br H₂O Na+ SCH3 (c) (d) CI "CH3arrow_forwardThe reaction of 1-bromopropane and sodium hydroxide in ethanol occurs by an SN2mechanism. What happens to the rate of this reaction under the following conditions?(a) The concentration of NaOH is doubled.(b) The concentrations of both NaOH and 1-bromopropane are doubled.(c) The volume of the solution in which the reaction is carried out is doubled.arrow_forward4 Which of the following alcohols could not be made selectively by hydroboration-oxidation of an alkene? Explain. about the (b) (a) (c) OH | CH3CH₂CH₂CHCH3 In H OH (CH3)2CHC(CH3)2 (d) CH3 vino zbiory 1 OH o no atou OH vollot edt evig H noituloa siblos V H но но CHO SHO=3₂HƆ m² CH3s 10 out of ST bewollot giaylonoso no WBTⱭ 12-8 His to edustrie 5 wode, $2-8 OnMX dilw osviel vitabarrow_forward
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