
(a)
Interpretation: The mechanism of given nucleophilic substitution reaction is to be determined and the products, along with their stereochemistry, are to be drawn.
Concept introduction: The replacement or substitution of one

Answer to Problem 7.69P
The mechanism of given nucleophilic substitution reaction is
Explanation of Solution
The structure of the given
In
However, in the given reaction halogen atom is not attached to chiral carbon. It is bonded to non-chiral carbon atom. The attack of nucleophile has not affect on the stereochemistry of reactant as shown in Figure 1.
Figure 1
The stereochemistry of reactant and product is same.
The mechanism of given nucleophilic substitution reaction is
(b)
Interpretation: The mechanism of given nucleophilic substitution reaction is to be determined and the products, along with their stereochemistry, are to be drawn.
Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as a nucleophile. In a nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking the electron deficient carbon atom.

Answer to Problem 7.69P
The mechanism of given nucleophilic substitution reaction is
Explanation of Solution
The structure of the given alkyl halide shows that a carbon atom, on which bromine atom is present, is bonded to two other carbon atoms. Hence, the bromine atom is bonded to secondary carbon atom. The removal of bromine atom leads to the formation of secondary carbocation. The secondary carbocation can undergo nucleophilic substitution reaction through both
In
Figure 2
The mechanism of given nucleophilic substitution reaction is
(c)
Interpretation: The mechanism of given nucleophilic substitution reaction is to be determined and the products, along with their stereochemistry, are to be drawn.
Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as a nucleophile. In a nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking the electron deficient carbon atom.

Answer to Problem 7.69P
The mechanism of given nucleophilic substitution reaction is
Explanation of Solution
The structure of the given alkyl halide shows that carbon atom, on which bromine atom is present, is bonded to three other carbon atoms. Hence, the bromine atom is bonded to tertiary carbon atom. The removal of bromine atom leads to the formation of planer tertiary carbocation. The tertiary carbocation is most likely to undergo nucleophilic substitution reaction by
In
Figure 3
The mechanism of given nucleophilic substitution reaction is
(d)
Interpretation: The mechanism of given nucleophilic substitution reaction is to be determined and the products, along with their stereochemistry, are to be drawn.
Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as a nucleophile. In a nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking the electron deficient carbon atom.

Answer to Problem 7.69P
The mechanism of given nucleophilic substitution reaction is
Explanation of Solution
The structure of the given alkyl halide shows that a carbon atom, on which iodine atom is present, is bonded to two other carbon atoms. Hence, the iodine atom is bonded to secondary carbon atom. The removal of iodine atom leads to the formation of secondary carbocation. The secondary carbocation can undergo nucleophilic substitution reaction through both
In
Figure 4
The mechanism of given nucleophilic substitution reaction is
(e)
Interpretation: The mechanism of given nucleophilic substitution reaction is to be determined and the products, along with their stereochemistry, are to be drawn.
Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as a nucleophile. In a nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking the electron deficient carbon atom.

Answer to Problem 7.69P
The mechanism of given nucleophilic substitution reaction is
Explanation of Solution
The structure of the given alkyl halide shows that a carbon atom, on which bromine atom is present, is bonded to two other carbon atoms. Hence, the bromine atom is bonded to secondary carbon atom. The removal of bromine atom leads to the formation of secondary carbocation. The secondary carbocation can undergo nucleophilic substitution reaction through both
In
Figure 5
The mechanism of given nucleophilic substitution reaction is
(f)
Interpretation: The mechanism of given nucleophilic substitution reaction is to be determined and the products, along with their stereochemistry, are to be drawn.
Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as a nucleophile. In a nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking the electron deficient carbon atom.

Answer to Problem 7.69P
The mechanism of given nucleophilic substitution reaction is
Explanation of Solution
The structure of the given alkyl halide shows that a carbon atom, on which bromine atom is present, is bonded to two other carbon atoms. Hence, the bromine atom is bonded to secondary carbon atom. The removal of bromine atom leads to the formation of secondary carbocation. The secondary carbocation can undergo nucleophilic substitution reaction through both
In
Figure 6
The mechanism of given nucleophilic substitution reaction is
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Chapter 7 Solutions
Organic Chemistry
- Assign all the carbonsarrow_forward9 7 8 C 9 8 200 190 B 5 A -197.72 9 8 7 15 4 3 0: ང་ 200 190 180 147.52 134.98 170 160 150 140 130 120 110 100 90 90 OH 10 4 3 1 2 -143.04 140. 180 170 160 150 140 130 120 110 100 90 CI 3 5 1 2 141.89 140.07 200 190 180 170 160 150 140 130 120 110 100 ៖- 90 129. 126.25 80 70 60 -60 50 40 10 125.19 -129.21 80 70 3.0 20 20 -8 60 50 10 ppm -20 40 128.31 80 80 70 60 50 40 40 -70.27 3.0 20 10 ppm 00˚0-- 77.17 30 20 20 -45.36 10 ppm -0.00 26.48 22.32 ―30.10 ―-0.00arrow_forwardAssign all the carbonsarrow_forward
- C 5 4 3 CI 2 the Righ B A 5 4 3 The Lich. OH 10 4 5 3 1 LOOP- -147.52 T 77.17 -45.36 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm B -126.25 77.03 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm 200 190 180 170 160 150 140 130 120 110 100 90 80 TO LL <-50.00 70 60 50 40 30 20 10 ppm 45.06 30.18 -26.45 22.36 --0.00 45.07 7.5 1.93 2.05 -30.24 -22.36 C A 7 8 5 ° 4 3 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm 9 8 5 4 3 ཡི་ OH 10 2 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 5 4 3 2 that th 7 I 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 115 2.21 4.00 1.0 ppm 6.96 2.76 5.01 1.0 ppm 6.30 1.00arrow_forwardCurved arrows were used to generate the significant resonance structure and labeled the most significant contribute. What are the errors in these resonance mechanisms. Draw out the correct resonance mechanisms with an brief explanation.arrow_forwardWhat are the: нсе * Moles of Hice while given: a) 10.0 ml 2.7M ? 6) 10.ome 12M ?arrow_forward
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- 7.5 1.93 2.05 C B A 4 3 5 The Joh. 9 7 8 1 2 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm 9 7 8 0.86 OH 10 4 3 5 1 2 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm 9 7 8 CI 4 3 5 1 2 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 2.21 4.00 1.5 2.00 2.07 1.0 ppm 2.76arrow_forwardAssign the functional group bands on the IR spectra.arrow_forwardFind the pH of a 0.120 M solution of HNO2. Find the pH ignoring activity effects (i.e., the normal way). Find the pH in a solution of 0.050 M NaCl, including activityarrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning

