
(a)
Interpretation:
It is to be shown how to carry out the given synthesis by using any reagents necessary.
Concept introduction:
Alkylation of carbonyl compound can take place at the α-carbon via nucleophilic substitution reaction. In this reaction acidic proton of the carbonyl compound is abstracted by the strong base an enolate anion is formed. The attack of this nucleophile takes place at the electrophilic carbon of the alkyl bromide and bromine atom is displaced through the

Answer to Problem 19.73P
The given synthesis is carried out as:
Explanation of Solution
The given synthesis:
So the given synthesis is carried out below:
In the first step, the nucleophilic addition of the enolate anion to the ethyl bromide takes place shown below:
Note than LDA is sterically hindered strong base, therefore, abstract less sterically hindered proton selectively.
Finally, the carbonyl group is reduced to a corresponding methylene group (
It is shown how to carry out the given synthesis by using any reagents necessary.
(b)
Interpretation:
It is to be shown how to carry out the given synthesis by using any reagents necessary.
Concept introduction:
Alkylation of carbonyl compound can take place at the α carbon via nucleophilic substitution reaction. In this reaction acidic proton of the carbonyl compound is abstracted by the strong base an enolate anion is formed. The attack of this nucleophile takes place at the electrophilic carbon of the alkyl bromide and bromine atom is displaced through

Answer to Problem 19.73P
The given synthesis is carried out as:
Explanation of Solution
The given synthesis is
So the given synthesis is carried out below:
In the first step, the nucleophilic addition of the enolate anion to the ethyl bromide takes place shown below:
The require nucleophile is generated by the treatment of the strong base
Finally, the carbonyl group is reduced to a corresponding methylene group (
It is shown how to carry out the given synthesis by using any reagents necessary.
(c)
Interpretation:
It is to be shown how to carry out the given synthesis by using any reagents necessary.
Concept introduction:
Lithium dialkylcuprate,

Answer to Problem 19.73P
The given synthesis is carried out as:
Explanation of Solution
The given synthesis is
It is noticed that one ethyl group is added to the 3-position of the original compound, therefore, the conjugate addition must be needed.
So the given synthesis is carried out below:
The first conjugate addition is carried out by the treatment of lithium diethylcuprate, a Gilman reagent with the given starting material. Since the conjugate addition is irreversible to the carbonyl group and regenerated during the workup step.
The above product then treated with ethyl bromide in the presence of a strong base
Finally, the carbonyl group is reduced to a corresponding methyl group (
It is shown how to carry out the given synthesis by using any reagents necessary.
(d)
Interpretation:
It is to be shown how to carry out the given synthesis by using any reagents necessary.
Concept introduction:
LDA is the strong non-nucleophilic base, due to bulky isopropyl groups. Therefore, it abstract proton of less sterically hindered α-carbon of the carbonyl compound. The reduction of the carbonyl group of a ketone to a methylene (

Answer to Problem 19.73P
The given synthesis is carried out as:
Explanation of Solution
The given synthesis is
It is noticed that the phenyl group is added to the carbonyl carbon of the given starting material. So Grignard reaction carried out first as below:
Since acidic condition required in workup step of Grignard reaction, the protected carbonyl group deprotected automatically because in acidic condition acetal protection also deprotect and the carbonyl group regenerated (right to the above product).
The alkylation of right carbon of the regenerated carbonyl compound is needed and it is done by using the sterically hindered base, LDA followed by methyl bromide. The bromine atom is replaced by a nucleophile (an enolate anion) via
The substrate is first treated with
Now the required alkylation is carried out as below:
Finally, the carbonyl group is reduced to a corresponding methylene group (
The protected OH in the form of OTBDMS is deprotected by the use of the source of
It is shown how to carry out the given synthesis by using any reagents necessary.
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Chapter 19 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
- Determine the structures of the missing organic molecules in the following reaction: + H₂O +H H+ Y Z ☑ ☑ Note: Molecules that share the same letter have the exact same structure. In the drawing area below, draw the skeletal ("line") structures of the missing organic molecules X, Y, and Z. You may draw the structures in any arrangement that you like, so long as they aren't touching. Molecule X shows up in multiple steps, but you only have to draw its structure once. Click and drag to start drawing a structure. AP +arrow_forwardPlease help, this is all the calculations i got!!! I will rate!!!Approx mass of KMnO in vial: 3.464 4 Moss of beaker 3×~0. z Nax200: = 29.9219 Massof weacerv after remosimgain N2C2O4. Need to fill in all the missing blanks. ง ง Approx mass of KMnO4 in vials 3.464 Mass of beaker + 3x ~0-304: 29.9219 2~0.20 Miss of beaker + 2x- 29.7239 Mass of beaker + 1x~0.2g Naz (204 29-5249 Mass of beaver after removing as qa Na₂ C₂O T1 T2 T3 Final Buiet reading Initial butet reading (int)) Hass of NaOr used for Titration -reading (mL) calculation Results: 8.5ml 17mL 27.4mL Oml Om Oml T1 T2 T3 Moles of No CO Moles of KMO used LOF KM. O used Molenty of KMNO Averagem Of KMOWLarrow_forwardDraw the skeletal ("line") structure of 2-hydroxy-4-methylpentanal. Click and drag to start drawing a structure. Xarrow_forward
- Determine whether the following molecule is a hemiacetal, acetal, or neither and select the appropriate box below. Also, highlight the hemiacetal or acetal carbon if there is one. hemiacetal acetal Oneither OHarrow_forwardWhat is the missing reactant R in this organic reaction? ་ ་ ་ ་ ་ ་ ་ ་ ་ ་ +R H3O+ • Draw the structure of R in the drawing area below. N • Be sure to use wedge and dash bonds if it's necessary to draw one particular enantiomer. Click and drag to start drawing a structure.arrow_forwardWrite the systematic name of each organic molecule: H structure H OH OH H OH name ☐ OHarrow_forward
- Determine whether each of the following molecules is a hemiacetal, acetal, or neither and select the appropriate box in the table. CH3O OH OH OH hemiacetal acetal neither hemiacetal acetal neither Xarrow_forwardWhat is the missing reactant R in this organic reaction? N N དལ་ད་་ + R • Draw the structure of R in the drawing area below. • Be sure to use wedge and dash bonds if it's necessary to draw one particular enantiomer. Click and drag to start drawing a structure. ㄖˋarrow_forwardDraw the condensed structure of 4-hydroxy-3-methylbutanal. Click anywhere to draw the first atom of your structure.arrow_forward
- Using the bond energy values, calculate the energy that must be supplied or is released upon the polymerization of 755 monomers. If energy must be supplied, provide a positive number; if energy is released, provide a negative number. Hint: Avogadro’s number is 6.02 × 1023.arrow_forward-AG|F=2E|V 3. Before proceeding with this problem you may want to glance at p. 466 of your textbook where various oxo-phosphorus derivatives and their oxidation states are summarized. Shown below are Latimer diagrams for phosphorus at pH values at 0 and 14: Acidic solution -0.93 +0.38 -0.51 -0.06 H3PO4 →H4P206 H3PO3 H3PO2 → P→ PH3 -0.28 -0.50 → -0.50 Basic solution 3-1.12 -1.57 -2.05 -0.89 PO HPO →→H2PO2 P PH3 -1.73 a) Under acidic conditions, H3PO4 can be reduced into H3PO3 directly (-0.28V), or via the formation and reduction of H4P2O6 (-0.93/+0.38V). Calculate the values of AG's for both processes; comment. (3 points) 0.5 PH, 0.0 -0.5- 2 3 9 3 -1.5 -2.0 Pa H,PO H,PO H,PO -3 -1 0 2 4 Oxidation state, N 2 b) Frost diagram for phosphorus under acidic conditions is shown. Identify possible disproportionation and comproportionation processes; write out chemical equations describing them. (2 points) c) Elemental phosphorus tends to disproportionate under basic conditions. Use data in…arrow_forwardThese two reactions appear to start with the same starting materials but result in different products. How do the chemicals know which product to form? Are both products formed, or is there some information missing that will direct them a particular way?arrow_forward
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