(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)
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- The carbonyl carbon is electrophilic and can undergo nucleophilic attack by carbon, oxygen, sulfur and nitrogen-containing nucleophiles. In this tutorial, we will focus on oxygen-containing nucleophiles, which form hydrates, hemiacetals and acetals. This tutorial will cover 1. formation of geminal diols or hydrates and when this reaction is favorable 2. formation of hemiacetals 3. formation of acetals 4. hydrolysis of hemiacetals and acetals 5. acetals as protecting groups O Macmillan Learning Step 4: The acetal formation mechanism is also reversible. The reaction can be driven in the forward reaction by using an excess of alcohol and driven in the reverse direction by using an excess of water. Analyze the reaction shown: excess H₂O* ? Select the product(s) of the reaction. HO HOCH₂CH₂OH HOarrow_forwardThe carbonyl carbon is electrophilic and can undergo nucleophilic attack by carbon, oxygen, sulfur and nitrogen-containing nucleophiles. In this tutorial, we will focus on oxygen-containing nucleophiles, which form hydrates, hemiacetals and acetals. This tutorial will cover 1. formation of geminal diols or hydrates and when this reaction is favorable 2. formation of hemiacetals 3. formation of acetals 4. hydrolysis of hemiacetals and acetals 5. acetals as protecting groups Macmillan Learning Step 4: The acetal formation mechanism is also reversible. The reaction can be driven in the forward reaction by using an excess of alcohol and driven in the reverse direction by using an excess of water. Analyze the reaction shown: excess H₂O* U Select the product(s) of the reaction. 8 ? & HOCH₂CH₂OH HO OHarrow_forwardWrite a stepwise reaction mechanism for the following sequence of reactions. i No 1) Ph 2) KCN/H,O CI CN Narrow_forward
- 4. Try using retrosynthesis to plan an efficient synthesis based on Grignard reactions for the following compounds from bromobenzene and any necessary organic or inorganic reagents. (a) Diphenylmethanol (b) 2-Phenylpropenearrow_forwardSynthesis. Provide the reagents necessary to synthesize the following compounds in a multistep synthesis. Be sure to use protecting groups, if and when necessary. (a) (b) Ph Br Ph Pharrow_forwardConvert phenylacetylene to butyl benzene using any necessary organic and inorganic reagents. It will require multiple steps.arrow_forward
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