
Draw the products formed when pentanal
a.
b.
c.
d.
e.
f.
g.
h.
i.
j.
k.
l. The [product in (a), then TBDMS-Cl, imidazole.

(a)
Interpretation: The product formed by the reaction of pentanal with
Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.
Answer to Problem 20.38P
The product formed by the reaction of pentanal with
Figure 1
Explanation of Solution
The reaction that shows the formation of product when pentanal reacts with
Figure 2
In the given reaction, sodium borohydride is used as a reducing agent. Sodium borohydride is used to for the reduction of carbonyl compounds to alcohols.
The product formed by the reaction of pentanal with

(b)
Interpretation: The product formed by the reaction of pentanal with
Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.
Answer to Problem 20.38P
The product formed by the reaction of pentanal with
Figure 1
Explanation of Solution
The reaction that shows the formation of product when pentanal reacts with
Figure 3
In the given reaction,
The product formed by the reaction of pentanal with

(c)
Interpretation: The product formed by the reaction of pentanal with the
Concept introduction: Addition of hydrogen takes place across a double bond of alkenes to form alkanes. This process is known as hydrogenation. It takes place in the presence of catalysts such as nickel, platinum or palladium.
Answer to Problem 20.38P
The product formed by the reaction of pentanal with the
Figure 1
Explanation of Solution
The reaction that shows the formation of product when
Figure 4
In the given reaction, hydrogenation of alkene takes place in the presence of palladium.
The product formed by the reaction of pentanal with the

(d)
Interpretation: The product formed by the reaction of pentanal with
Concept introduction:
Answer to Problem 20.38P
No product is formed by the reaction of pentanal with
Explanation of Solution
The product formed by the reaction of pentanal with
Figure 5
No product is formed by the reaction of pentanal with

(e)
Interpretation: The product formed by the reaction of pentanal with the
Concept introduction: Organometallic reagents like
Answer to Problem 20.38P
The product formed by the reaction of pentanal with the
Figure 6
Explanation of Solution
The product formed by the reaction of pentanal with the
Figure 7
The product formed by the reaction of pentanal with the

(f)
Interpretation: The product formed by the reaction of pentanal with
Concept introduction:
Answer to Problem 20.38P
The product formed by the reaction of pentanal with
Figure 6
Explanation of Solution
The product formed by the reaction of pentanal with
Figure 8
The product formed by the reaction of pentanal with

(g)
Interpretation: The product formed by the reaction of pentanal with the
Concept introduction: Grignard reagent is prepared by the reaction of alkyl or aryl bromide with magnesium metal in the presence of ether. The reaction of Grignard reagent with an aldehyde/ketone followed by hydrolysis yields an alcohol.
Answer to Problem 20.38P
The product formed by the reaction of pentanal with the
Figure 9
Explanation of Solution
The reaction that shows the formation of product when
Figure 10
In the given reaction, Grignard reagent is used. This reagent attacks on the carbonyl compound to form alkoxides. In the next step, protonation with water takes place to give the final product.
The product formed by the reaction of pentanal with the

(h)
Interpretation: The product formed by the reaction of pentanal with
Concept introduction: Organometallic reagents like
Answer to Problem 20.38P
The product formed by the reaction of pentanal with
Figure 11
Explanation of Solution
The reaction that shows the formation of product when
Figure 12
The product formed by the reaction of pentanal with

(i)
Interpretation: The product formed by the reaction of pentanal with
Concept introduction: Organometallic reagents like
Answer to Problem 20.38P
No product formed by the reaction of pentanal with
Explanation of Solution
The product formed by the reaction of pentanal with
Figure 13
Aldehydes do not react with organo copper reagent because these reagents are less reactive and cannot attack to the electrophilic centre of the aldehyde group.

(j)
Interpretation: The product formed by the reaction of pentanal with
Concept introduction: Organometallic reagents like
Answer to Problem 20.38P
The product formed by the reaction of pentanal with
Figure 14
Explanation of Solution
The product formed by the reaction of pentanal with
Figure 15

(k)
Interpretation: The product formed by the reaction of pentanal with
Concept introduction: Organometallic reagents like
Answer to Problem 20.38P
The product formed by the reaction of pentanal with
Figure 16
Explanation of Solution
The reaction that shows the formation of product when
Figure 17

(l)
Interpretation: The product formed by the reaction of pentanal with
Concept introduction: Organometallic reagents like
Answer to Problem 20.38P
The product formed by the reaction of pentanal with
Figure 18
Explanation of Solution
The product formed by the reaction of pentanal with
Figure 19
In the given reaction, sodium borohydride is used as a reducing agent. Sodium borohydride is used to for the reduction of carbonyl compounds to alcohols.
The product formed by the reaction of pentanal with the
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Chapter 20 Solutions
ORGANIC CHEMISTRY
- ion. A student proposes the following Lewis structure for the perchlorate (CIO) io : :0: : Cl : - - : :0: ك Assign a formal charge to each atom in the student's Lewis structure. atom central O formal charge ☐ top O ☐ right O ☐ bottom O ☐ Cl ☐arrow_forwardDecide whether these proposed Lewis structures are reasonable. proposed Lewis structure Yes. Is the proposed Lewis structure reasonable? Cl- : 2: :Z: :Z: N—N : 0: C C1: O CO No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* ☐ Yes. No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* | Yes. No, it has the wrong number of valence electrons. The correct number is: No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* | If two or more atoms of the same element don't satisfy the octet rule, just enter the chemical symbol as many times as necessary. For example, if two oxygen atoms don't satisfy the octet rule, enter "0,0". ☑arrow_forwardUse the observations about each chemical reaction in the table below to decide the sign (positive or negative) of the reaction enthalpy AH and reaction entropy AS. Note: if you have not been given enough information to decide a sign, select the "unknown" option. reaction observations conclusions ΔΗ is (pick one) A This reaction is faster above 103. °C than below. AS is (pick one) ΔΗ is (pick one) B This reaction is spontaneous only above -9. °C. AS is (pick one) ΔΗ is (pick one) C The reverse of this reaction is always spontaneous. AS is (pick one) 18 Ararrow_forward
- Use the observations about each chemical reaction in the table below to decide the sign (positive or negative) of the reaction enthalpy AH and reaction entropy AS. Note: if you have not been given enough information to decide a sign, select the "unknown" option. reaction observations conclusions A The reverse of this reaction is always spontaneous but proceeds slower at temperatures below 41. °C. ΔΗ is (pick one) AS is (pick one) ΔΗ is (pick one) B This reaction is spontaneous except above 94. °C. AS is (pick one) This reaction is always spontaneous, but ΔΗ is (pick one) C proceeds slower at temperatures below −14. °C. AS is (pick one) Х 00. 18 Ar 무ㅎ B 1 1arrow_forwardDraw the product of the reaction shown below. Ignore inorganic byproducts. + H CH3CH2OH HCI Drawingarrow_forwardplease explain this in simple termsarrow_forward
- K Most Reactive Na (3 pts) Can the metal activity series (shown on the right) or a standard reduction potential table explain why potassium metal can be prepared from the reaction of molten KCI and Na metal but sodium metal is not prepared from the reaction of molten NaCl and K metal? Show how (not). Ca Mg Al с Zn Fe Sn Pb H Cu Ag Au Least Reactivearrow_forward(2 pts) Why is O2 more stable as a diatomic molecule than S2?arrow_forwardDraw the Lewis structure for the polyatomic phosphite (PO¾³¯) a anion. Be sure to include all resonance structures that satisfy the octet rule. C I A [ ]¯arrow_forward
- Decide whether these proposed Lewis structures are reasonable. proposed Lewis structure Is the proposed Lewis structure reasonable? Yes. :0: Cl C C1: 0=0: : 0 : : 0 : H C N No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* ☐ Yes. No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* Yes. ☐ No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* | * If two or more atoms of the same element don't satisfy the octet rule, just enter the chemical symbol as many times as necessary. For example, if two oxygen atoms don't satisfy the octet rule, enter "0,0".arrow_forwardDraw the Lewis structure for the polyatomic trisulfide anion. Be sure to include all resonance structures that satisfy the octet rule. с [ ] - Garrow_forward1. Calculate the accurate monoisotopic mass (using all 1H, 12C, 14N, 160 and 35CI) for your product using the table in your lab manual. Don't include the Cl, since you should only have [M+H]*. Compare this to the value you see on the LC-MS printout. How much different are they? 2. There are four isotopic peaks for the [M+H]* ion at m/z 240, 241, 242 and 243. For one point of extra credit, explain what each of these is and why they are present. 3. There is a fragment ion at m/z 184. For one point of extra credit, identify this fragment and confirm by calculating the accurate monoisotopic mass. 4. The UV spectrum is also at the bottom of your printout. For one point of extra credit, look up the UV spectrum of bupropion on Google Images and compare to your spectrum. Do they match? Cite your source. 5. For most of you, there will be a second chromatographic peak whose m/z is 74 (to a round number). For one point of extra credit, see if you can identify this molecule as well and confirm by…arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
