question 1: Propose a synthesis of the compound below on the left from ethyl acetoacetate (ethyl 3-oxobutanoate). You may use any of the reagents in the table.
question 2:
Each of the compounds below is treated with a large molar excess of D2O containing a catalytic amount of NaOD. When this is done all of the acidic hydrogens are exchanged for deuteriums. Indicate the number of hydrogens exchanged on each compound.
question 3: Indicate whether the compounds below undergo
racemization when treated with aqueous acid or base.
Optical activity: optical activity is a property of rotation of the plane polarized light when passed through certain organic sample which has chiral center.
Acetoacetate ester synthesis: Conversion of ethyl Acetoacetate to ketone after alkylating the alpha carbon between 2 carbonyl groups.
When treating the chemical compound by with catalytic amount of , the hydrogen which is present near to the carbonyl group (alpha hydrogen) is more acidic and that will be exchanged with deuterium.
The conversion of optically active compound into optically inactive one is called as racemization. If the compound contains chiral center with alpha hydrogen present in the chiral center, then the compound will undergo racemization.
The acidic hydrogen in the carbonyl compound:
In the above compound, the highlighted hydrogens are acidic hydrogens.
Racemization will occur in the compound:
Chiral center: It can be defined as in a molecule, where the carbon is bonded to four non identical substituents.
The formation of the given compound is shown below.
(1)
The reagents are
(2)
Exchanged hydrogens are marked in red.
(3)
The compounds that undergo racemization are shown below.
The letters of the reagents in order is given below:
Part 2
Number of hydrogen exchanged in each compound is given below:
The compound that undergoes racemization when treated with aqueous acid or base is given below:
question 1: Propose a synthesis of the compound below on the left from ethyl acetoacetate (ethyl...
Propose a synthesis of the compound below on the left from ethyl actoacetate (ethyl 3-oxobutanoate). You may use any of the reagents in the table. Reagents available a. CH, Br d. b. CH, CH, Br h. H, O, heat { NOCH H OH List the letters of the reagents in the order you would use them, example Submit Answer Try Another Version 1 item attempt remaining Previou
Propose a synthesis of the compound below. Use one of the two starting materials and any of the reagents in the table. H2C=CHCH2CH2CCH3 Reagents available Starting materials CHCHBO n Br 유 1. CH3CCH2CO E 2 CHCOMEN)2 Br a. CH, Br b. CH3CH2Br Br Br Br | Br Br Br Br CH,Br 1. BrCH CH Br CH,Br 9. BI Br m r. HjO", heat 3. NaOCHy/C,H,OH h Br CHBO Br List the number of the starting material and then the letters...
identify which compound is more acidic and explain your choice. or each of the following compounds, Make sure you include structures of these which compounds in your answers ounds, 1. F (e) 24-Dimethy-3,5-hepanedione or 4, 4-Dimethy)-3,5-heptanedione (b) 1.2-Cyclopentanedione or 1,3-cyclopentanedione 2. When 2-hepten-4-one is treated with LDA, a proton is removed from one of the gamma (z) positions. identily which gamma position is deprotonated, and explain why the y proton is the most acidie proton in the compound. 3. Rank...
8. Give a synthesis of the compound shown starting from either diethyl malonate (DEM) or ethyl acetoacetate (EAA) shown in the box below. Give all reagents necessary. State clearly whether your starting compound is DEM or EAA. You do not need to draw the intermediate steps. 17 pts] Eto Et Hoce DEM ΕΑΑ. 9. Draw the uncharged product of this synthetic sequence. [4 pts] 1. KOH OCH 3. NaOH(aq) excess 10. By how much will the mass of this compound...
Part IV - Multistep Synthesis [14 marks] A. Propose a synthesis of compound A starting from dimethyl malonate. When choosing your synthetic steps, you can use any hydrocarbon with three or fewer carbon atoms, any solvents or inorganic reagents, and any organic reagents that do not contribute carbon atoms to the carbon skeleton in the product. Clearly show the required reagents and the product of each step. You do not need to show mechanistic (curved) arrows. [6 marks] Dimethyl malonate...
Help with question in image. thankyou.
Propose a synthesis of compound B from (R)-2-chlorobutane. When choosing your synthetic steps, you can use any hydrocarbon with three or fewer carbon atoms, any solvents or inorganic reagents, and any organic reagents that do not contribute carbon atoms to the carbon skeleton in the product. Clearly show the required reagents and the product of each step. You do not need to show mechanistic (curved) arrows. CI (R)-2-chlorobutane B
Propose an efficient synthesis of the compound shown below, starting from acetylene and methyl iodide. You may use any other reagents as necessary, but all carbons in the product must originate from acetylene and methyl iodide.
Part IV - Multistep Synthesis cont'd Propose a synthesis of compound B from (R)-2-chlorobutane. When choosing your synthetic steps, you can use any hydrocarbon with three or fewer carbon atoms, any solvents or inorganic reagents, and any organic reagents that do not contribute carbon atoms to the carbon skeleton in the product. Clearly show the required reagents and the product of each step. You do not need to show mechanistic (curved) arrows. CI (R)-2-chlorobutane B
Using the reagents list below, propose a synthesis of the
target compound starting from benzene. Enter your answers as a list
of letters corresponding to the selected reagents in order you wish
to use them. You may assume that all reactions are appropriately
worked up and that mixtures of comstitutional isomers can be
separated
Remaining Time: 59 minutes, 08 seconds. Question Completion Status: Moving to another question will save this response. Question 1 Using the reagents listed below, propose a...
the most efficient synthesis possible 6. Synthesis propose to make the compound shown below Starting from benzene. Be sure to include appropriate reaction conditions and products for each step. Steps HO NHL