
Concept explainers
(a)
Interpretation: The given compound is to be classified as identical to
Concept introduction: The stereochemistry of the compound is determined by prioritizing the groups attached to its stereogenic center. The groups are prioritized on the basis of

Answer to Problem 28.39P
The given compound is classified as identical to
Explanation of Solution
The structure of compound
Figure 1
In the compound
Figure 2
The circle rotates in the anticlockwise direction and its configuration will be
Figure 3
Thus, the configuration will reverse. Therefore, the compound
The given compound is,
Figure 4
In the given compound,
Figure 5
The circle rotates in the clockwise direction. Thus, the given compound is labeled as
Hence, the given compound is classified as identical to
The given compound is classified as identical to
(b)
Interpretation: The given compound is to be classified as identical to
Concept introduction: The stereochemistry of the compound is determined by prioritizing the groups attached to its stereogenic center. The groups are prioritized on the basis of atomic number of their atoms. The group that contain atom with higher atomic number is given higher priority. Complete the circle in decreasing order of priority from

Answer to Problem 28.39P
The given compound is classified as identical to
Explanation of Solution
The compound
The given compound is,
Figure 6
In the given compound,
Figure 7
The circle rotates in the anticlockwise direction hence its configuration will be
Figure 8
Thus, the configuration will reverse. Therefore, the compound is labeled as
Hence, the given compound is classified as identical to
The given compound is classified as identical to
(c)
Interpretation: The given compound is to be classified as identical to
Concept introduction: The stereochemistry of the compound is determined by prioritizing the groups attached to its stereogenic center. The groups are prioritized on the basis of atomic number of their atoms. The group that contain atom with higher atomic number is given higher priority. Complete the circle in decreasing order of priority from

Answer to Problem 28.39P
The given compound is classified as enantiomer to
Explanation of Solution
The compound
The given compound is,
Figure 9
In the given compound,
Figure 10
The circle rotates in the clockwise direction hence its configuration will be
Figure 11
Thus, the configuration will reverse. Therefore, the compound is labeled as
Hence, the given compound is classified as enantiomer to
The given compound is classified as enantiomer to
(d)
Interpretation: The given compound is to be classified as identical to
Concept introduction: The stereochemistry of the compound is determined by prioritizing the groups attached to its stereogenic center. The groups are prioritized on the basis of atomic number of their atoms. The group that contain atom with higher atomic number is given higher priority. Complete the circle in decreasing order of priority from

Answer to Problem 28.39P
The given compound is classified as enantiomer to
Explanation of Solution
The compound
The given compound is,
Figure 12
In the given compound,
Figure 13
The circle rotates in the clockwise direction hence its configuration will be
Figure 14
Thus, the configuration will reverse. Therefore, the compound is labeled as
The given compound and
Figure 15
Hence, the given compound is classified as enantiomer to
The given compound is classified as enantiomer to
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Chapter 28 Solutions
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- If cyclopentyl acetaldehyde reacts with NaOH, state the product (formula).arrow_forwardDraw the major product of this reaction. Ignore inorganic byproducts. N S S HgCl2, H2SO4 く 8 W X Parrow_forwardtab esc く Drawing the After running various experiments, you determine that the mechanism for the following reaction occurs in a step-wise fashion. Br + OH + Using this information, draw the correct mechanism in the space below. 1 Explanation Check F2 F1 @2 Q W A os lock control option T S # 3 80 F3 Br $ 4 0105 % OH2 + Br Add/Remove step X C F5 F6 6 R E T Y 29 & 7 F D G H Click and drag to start drawing a structure. © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Ce A F7 DII F8 C Ո 8 * 9 4 F10 F C J K L C V Z X B N M H command P ge Coarrow_forward
- Indicate compound A that must react with ethylbenzene to obtain 4-ethylbenzene-1-sulfonic acid. 3-bromo-4-ethylbenzene-1-sulfonic acid.arrow_forwardPart 1 of 2 Draw the structure of A, the minor E1 product of the reaction. esc I Skip Part Check H₂O, D 2 A + Click and drag to start drawing a structure. -0- F1 F2 1 2 # 3 Q A 80 F3 W E S D F4 $ 4 % 5 F5 ㅇ F6 R T Y F G X 5 & 7 + Save 2025 McGraw Hill LLC. All Rights Reserved. DII F7 F8 H * C 80 J Z X C V B N 4 F9 6arrow_forwardFile Preview The following is a total synthesis of the pheromone of the western pine beetle. Such syntheses are interesting both because of the organic chemistry, and because of the possibility of using species specific insecticides, rather than broad band insecticides. Provide the reagents for each step. There is some chemistry from our most recent chapter in this synthesis, but other steps are review from earlier chapters. (8 points) COOEt COOEt A C COOEt COOEt COOH B OH OTS CN D E See the last homework set F for assistance on this one. H+, H₂O G OH OH The last step is just nucleophilic addition reactions, taking the ketone to an acetal, intramolecularly. But it is hard to visualize the three dimensional shape as it occurs. Frontalin, pheromone of the western pine beetlearrow_forward
- For the reaction below: 1. Draw all reasonable elimination products to the right of the arrow. 2. In the box below the reaction, redraw any product you expect to be a major product. C Major Product: Check + ◎ + X ง © Cl I F2 80 F3 I σ F4 I F5 NaOH Click and drawing F6 A 2025 McGraw Hill LLC. All Rights E F7 F8 $ # % & 2 3 4 5 6 7 8 Q W E R T Y U A S D F G H Jarrow_forwardCan I please get help with this graph. If you can show exactly where it needs to pass through.arrow_forwardN Draw the major product of this reaction. Ignore inorganic byproducts. D 1. H₂O, pyridine 2. neutralizing work-up V P W X DE CO e C Larrow_forward
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