(a)
Interpretation:
It is to be shown how a retrosynthetic analysis might be constructed for the given synthesis.
Concept introduction:
Retrosynthesis is the planning of
Answer to Problem 13.30P
The retrosynthesis for the given synthesis is
Explanation of Solution
The given synthetic reaction is
In the given synthesis, the product differs from the starting compound by one ethyl group bonded to six-membered ring. Thus, the bond between the ethyl group and ring carbon in the target must break to transform it to the starting compound.
Therefore, retrosynthesis for the given synthetic reaction is
The retrosynthesis for the given synthetic reaction is shown by disconnecting the ethyl group from the ring.
(b)
Interpretation:
It is to be shown how a retrosynthetic analysis might be constructed for the given synthesis.
Concept introduction:
Retrosynthesis is the planning of organic synthesis, working backwards from target molecule to a simpler precursor, regardless of any interaction with reagents. Thus, the basis of retrosynthetic analysis is the transform, which means the reverse of a synthetic reaction. The precursors are the compounds, which are either readily available or easy to produce. The transform is indicated by an open arrow
Answer to Problem 13.30P
The retrosynthesis for the given synthesis is
Explanation of Solution
The given synthetic reaction is
The given synthesis is of two steps; the final product is the target molecule. Thus, retrosynthesis could be planned from the target to the intermediate product to the starting material. The target molecule and the intermediate product differ in bromine and cyanide. Thus, the bond between the cyanide and ring carbon must break to transform into an intermediate. The intermediate and the starting molecule differ by bromine atom. Thus, the bond between the bromine and ring carbon must break to transform into the starting material.
Therefore, the retrosynthesis for the given synthetic reaction is
The retrosynthesis for the given synthetic reaction is shown by disconnecting the cyanide group and then by disconnecting the bromine atom from the ring.
(c)
Interpretation:
It is to be shown how a retrosynthetic analysis might be constructed for the given synthesis.
Concept introduction:
Retrosynthesis is the planning of organic synthesis, working backwards from target molecule to a simpler precursor, regardless of any interaction with reagents. Thus, the basis of retrosynthetic analysis is the transform, which means the reverse of a synthetic reaction. The precursors are the compounds, which are either readily available or easy to produce. The transform is indicated by an open arrow
Answer to Problem 13.30P
The retrosynthesis for the given synthesis is
Explanation of Solution
The given synthetic reaction is
The given synthesis is of two steps; the final product is the target molecule. Thu, s the retrosynthesis could be planned from the target to the intermediate product to the starting material. The target molecule and the intermediate product differ in the benzyl group attached to the triple bonded carbon. Thus, the bond between the benzylic carbon and triple bonded carbon must break to transform into an intermediate. The intermediate can be transformed into the starting material by replacing the methyl group bonded to the oxygen atom by hydrogen.
Therefore, the retrosynthesis for the given synthetic reaction is
The retrosynthesis for the given synthetic reaction is shown by disconnecting the benzyl group from the triple bonded carbon and then by disconnecting the methyl group from the oxygen atom.
(d)
Interpretation:
It is to be shown how a retrosynthetic analysis might be constructed for the given synthesis.
Concept introduction:
Retrosynthesis is the planning of organic synthesis, working backwards from target molecule to a simpler precursor, regardless of any interaction with reagents. Thus, the basis of retrosynthetic analysis is the transform, which means the reverse of a synthetic reaction. The precursors are the compounds, which are either readily available or easy to produce. The transform is indicated by an open arrow
Answer to Problem 13.30P
The retrosynthesis for the given synthesis is
Explanation of Solution
The given synthetic reaction is
The given synthesis is of two steps; the final product is the target molecule. Thus the retrosynthesis could be planned from the target to the intermediate product to the starting material. The target molecule has a double bond, which is removed in the intermediate product having the ydroxyl group at that position. Thus, the
Therefore, the retrosynthesis for the given synthetic reaction is
The retrosynthesis for the given synthetic reaction is shown by disconnecting the
(e)
Interpretation:
It is to be shown how a retrosynthetic analysis might be constructed for the given synthesis.
Concept introduction:
Retrosynthesis is the planning of organic synthesis, working backwards from target molecule to a simpler precursor, regardless of any interaction with reagents. Thus, the basis of retrosynthetic analysis is the transform, which means the reverse of a synthetic reaction. The precursors are the compounds, which are either readily available or easy to produce. The transform is indicated by an open arrow
Answer to Problem 13.30P
The retrosynthesis for the given synthesis is
Explanation of Solution
The given synthetic reaction is
The given synthesis is of three steps; the final product is the target molecule. Thus, the retrosynthesis could be planned from the target to the second intermediate, then to the first intermediate, and finally into the starting material. The target molecule has the acetate group at the alpha position and the second intermediate has the bromine atom; thus, the bond between the alpha carbon and the oxygen of the acetate group must break. The second intermediate can be transformed into the first intermediate by breaking the bond between bromine and the alpha carbon. The first intermediate and the starting molecule differ by an additional methyl group; thus the bond between the alpha carbon and methyl must break to show the transform.
Therefore, the retrosynthesis for the given synthetic reaction is
The retrosynthesis for the given synthetic reaction is shown by disconnecting appropriate bonds.
(g)
Interpretation:
It is to be shown how a retrosynthetic analysis might be constructed for the given synthesis.
Concept introduction:
Retrosynthesis is the planning of organic synthesis, working backwards from target molecule to a simpler precursor, regardless of any interaction with reagents. Thus, the basis of retrosynthetic analysis is the transform, which means the reverse of a synthetic reaction. The precursors are the compounds, which are either readily available or easy to produce. The transform is indicated by an open arrow
Answer to Problem 13.30P
The retrosynthesis for the given synthesis is
Explanation of Solution
The given synthetic reaction is
The given synthesis is of three steps; the final product is the target molecule. Thus; the retrosynthesis could be planned from the target to the second intermediate; then to the first intermediate; and finally into the starting material. The target can be transformed to the second intermediate by replacing the nitride group by bromine; thus the bond between the nitride group and carbon must break. The second intermediate can be transformed into the first intermediate by replacing the bromine by hydroxyl group; thus the bond between bromine and carbon must break. The first intermediate can be transformed into the starting material by replacing the hydroxyl group by ethoxy group.
Therefore, the retrosynthesis for the given synthetic reaction is
The retrosynthesis for the given synthetic reaction is shown by disconnecting appropriate bonds.
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Chapter 13 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
- Draw the Haworth projection of the disaccharide made by joining D-glucose and D-mannose with a ẞ(1-4) glycosidic bond. If the disaccharide has more than one anomer, you can draw any of them. Click and drag to start drawing a structure. Xarrow_forwardEpoxides can be opened in aqueous acid or aqueous base to produce diols (molecules with two OH groups). In this question, you'll explore the mechanism of epoxide opening in aqueous acid. 2nd attempt Be sure to show all four bonds at stereocenters using hash and wedge lines. 0 0 Draw curved arrows to show how the epoxide reacts with hydronium ion. 100 +1: 1st attempt Feedback Be sure to show all four bonds at stereocenters using hash and wedge lines. See Periodic Table See Hint H A 5 F F Hr See Periodic Table See Hintarrow_forward03 Question (1 point) For the reaction below, draw both of the major organic products. Be sure to consider stereochemistry. > 1. CH₂CH₂MgBr 2. H₂O 3rd attempt Draw all four bonds at chiral centers. Draw all stereoisomers formed. Draw the structures here. e 130 AN H See Periodic Table See Hint P C Brarrow_forward
- You may wish to address the following issues in your response if they are pertinent to the reaction(s) you propose to employ:1) Chemoselectivity (why this functional group and not another?) 2) Regioselectivity (why here and not there?) 3) Stereoselectivity (why this stereoisomer?) 4) Changes in oxidation state. Please make it in detail and draw it out too in what step what happens. Thank you for helping me!arrow_forward1) Chemoselectivity (why this functional group and not another?) 2) Regioselectivity (why here and not there?) 3) Stereoselectivity (why this stereoisomer?) 4) Changes in oxidation state. Everything in detail and draw out and write it.arrow_forwardCalculating the pH at equivalence of a titration 3/5 Izabella A chemist titrates 120.0 mL of a 0.7191M dimethylamine ((CH3)2NH) solution with 0.5501 M HBr solution at 25 °C. Calculate the pH at equivalence. The pk of dimethylamine is 3.27. 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 HBr solution added. pH = ☐ ✓ 18 Ar Boarrow_forward
- Alcohols can be synthesized using an acid-catalyzed hydration of an alkene. An alkene is combined with aqueous acid (e.. sulfuric acid in water). The reaction mechanism typically involves a carbocation intermediate. > 3rd attempt 3343 10 8 Draw arrows to show the reaction between the alkene and hydronium ion. that 2nd attempt Feedback 1st attempt تعمال Ju See Periodic Table See Hint F D Ju See Periodic Table See Hintarrow_forwardDraw the simplified curved arrow mechanism for the reaction of acetone and CHgLi to give the major product. 4th attempt Π Draw the simplified curved arrow mechanism T 3rd attempt Feedback Ju See Periodic Table See Hint H -H H -I H F See Periodic Table See Hintarrow_forwardSelect the correct reagent to accomplish the first step of this reaction. Then draw a mechanism on the Grignard reagent using curved arrow notation to show how it is converted to the final product. 4th attempt Part 1 (0.5 point) Select the correct reagent to accomplish the first step of this reaction. Choose one: OA Mg in ethanol (EtOH) OB. 2 Li in THF O C. Li in THF D. Mg in THF O E Mg in H2O Part 2 (0.5 point) Br Part 1 Bri Mg CH B CH, 1 Draw intermediate here, but no arrows. © TE See Periodic Table See Hint See Hint ין Harrow_forward
- Select the product for the following reaction. HO HO PCC OH ○ OH O HO ○ HO HO HOarrow_forward5:45 Х Select the final product for the following reaction sequence. O O 1. Mg. ether 2.D.Oarrow_forwardBased on the chart Two similarities between the molecule with alpha glycosidic linkages. Two similarities between the molecules with beta glycosidtic linkages. Two differences between the alpha and beta glycosidic linkages.arrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning