Concept explainers
(a)
Interpretation:
The principal organic product that is obtained when
Concept introduction:
The reaction in which an atom of
Answer to Problem 26.26AP
The principal organic product that is obtained when
Explanation of Solution
The reaction of
Figure 1
In the above reaction, the second position of
Therefore, the product formed by the above reaction is
The principal organic product,
(b)
Interpretation:
The principal organic product that is obtained when
Concept introduction:
The reaction in which an atom of aromatic system is replaced by an electrophile is known as electrophilic aromatic substitution reaction. The compound, acetic anhydride behaves as a acetylating compound in the presence of
Answer to Problem 26.26AP
The principal organic product that is obtained when
Explanation of Solution
The reaction of
Figure 2
In the above reaction, the second position of
Therefore, the product formed by the above reaction is
The principal organic product,
(c)
Interpretation:
The incomplete reaction between diene and dienophile is to be completed with the reasonable products. The reason corresponding to the formation of the correct product is to be explained.
Concept introduction:
Diels Alder reaction is the
Answer to Problem 26.26AP
The complete reaction is shown below.
Explanation of Solution
The given incomplete reaction is shown below.
Figure 3
In the above incomplete reaction, the given
Figure 4
Therefore, one product is obtained from the above shown Diels Alder reaction.
The complete reaction corresponding to the incomplete reaction between diene and dienophile is shown in Figure 4.
(d)
Interpretation:
The incomplete reaction between an alkene and benzoquinone is to be completed with the reasonable products. The reason corresponding to the formation of the correct product is to be explained.
Concept introduction:
Diels Alder reaction is the
Answer to Problem 26.26AP
The complete reaction is shown below.
Explanation of Solution
The given incomplete reaction is shown below.
Figure 5
In the above incomplete reaction, the given two equivalents of alkene behaves as a diene and undergoes Diels Alder reaction with benzoquinone which behaves as a dienophile in the presence of heat to form two products as shown below.
Figure 6
Therefore, two products are obtained from the above shown Diels Alder reaction. The second product is the major one because of the less van der Waals repulsion present in between two double bonds which are exocyclic.
The complete reaction corresponding to the incomplete reaction between diene and dienophile is shown in Figure 6.
(e)
Interpretation:
The incomplete reaction between a diene and a dienophile is to be completed with the reasonable products. The reason corresponding to the formation of the correct product is to be explained.
Concept introduction:
Diels Alder reaction is the
Answer to Problem 26.26AP
The complete reaction is shown below.
Explanation of Solution
The given incomplete reaction is shown below.
Figure 7
Only the
Figure 8
The above reaction does not form any product because the
Therefore, no product is formed in the above shown reaction.
There is no formation of the product takes place in the given reaction.
(f)
Interpretation:
The incomplete reaction between a diene and a dienophile is to be completed with the reasonable products. The reason corresponding to the formation of the correct product is to be explained.
Concept introduction:
Diels Alder reaction is the
Answer to Problem 26.26AP
The complete reaction is shown below.
Explanation of Solution
The given incomplete reaction is shown below.
Figure 9
In the above incomplete reaction, the intramolecular Diels Alder reaction takes place in the presence of heat to form two products as shown below.
Figure 10
In the above reaction, diene and dienophile are present in the same compound. Therefore, two products are obtained from the above shown Diels Alder reaction. Therefore, the shifting of bonds takes place within the molecule to form a single product.
The complete reaction corresponding to the incomplete reaction between diene and dienophile is shown in Figure 10.
(g)
Interpretation:
The incomplete reaction between nickel choride and
Concept introduction:
Metallocene compounds are composed of an electropositive metal ions specially
Answer to Problem 26.26AP
The complete reaction is shown below.
Explanation of Solution
The given incomplete reaction is shown below.
Figure 11
In the above incomplete reaction, the nickel chloride reacts with
Figure 12
Therefore, the reaction between nickel chloride and
The complete reaction corresponding to the incomplete reaction between nickel choride and
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Chapter 26 Solutions
Organic Chemistry
- 1. Predict the products or the reaction of (i) phenylacetaldehyde and (ii) acetophenone with the following reagents: (a) NABH4, then H0+ (c) NH2OH, HCI catalyst (e) 2 CH3OH, HCl catalyst (g) (CH3)3P=CH, (b) Tollens' reagent (cl) CHĄMgBr, then H30+ (t) H2NNH2. KOH (h) HCN, KCNarrow_forwardPredict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.(a) ethanol (b) sodium acetate (c) anilinearrow_forwardWhich of the following reactions will synthesize phenol from benzene? 1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) warm H2SO4 and H2O 1) HNO3 + H2SO4; 2) Fe, HCl; 3) NaNO2, HCl, 0-10 oC; 4) CuCN; 5) dilute acid and heat 1) Acetyl chloride & AlCl3; 2) bleach 1) Ph-N2+ + KI; 2) BrMgCH=CH2 in ether, followed by H3O+; 3) warm, conc'd KMnO4 1) Cl-CH(CH3)-CH2CH2CH3 + FeBr3; 2) hot, conc'd KMnO4arrow_forward
- Draw line structures of the following compounds and the product you would obtain from the reduction of each.(a) Isopropyl methyl ketone (b) p-Hydroxybenzaldehyde(c) 2-Methylcyclopentanonearrow_forward(a) How will you convert:(i) Benzene to acetophenone (ii) Propanone to 2-Methylpropan-2-ol(b) Give reasons :(i) Electrophilic substitution in benzoic acid takes place at meta position.(ii) Carboxylic acids are higher boiling liquids than aldehydes, ketones and alcohols of comparable molecular masses.(iii) Propanal is more reactive than propanone in nucleophilic addition reactions.arrow_forward22). What is the major product of the following reactions? (A) (B) Br 1) NaCN 2) CH3MgBr 3) H30*/H₂O (C) LOH (D) CNarrow_forward
- Which, if any, of the following compounds can be prepared by a malonic ester synthesis? Show the alkyl halide you would use in each case. (a) Ethyl pentanoate (c) Ethyl 2-rnethylbutanoate (d) Ethyl 2,2-dimethylpropanoate (b) Ethyl 3-methylbutanoatearrow_forwardPredict the major products formed when benzene reacts (just once) with the following reagents.(a) tert-butyl bromide, AlCl3 (b) 1-chlorobutane, AlCl3(c) isobutyl alcohol + BF3 (d) bromine + a nail(e) isobutylene + HF (f) fuming sulfuric acidarrow_forwardThe following questions concern ethyl (2-oxocyclohexane)carboxylate.(a) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by a Dieckmann cyclization.(b) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by acylation of a ketone.(c) Write structural formulas for the two most stable enol forms of ethyl (2-oxocyclohexane)carboxylate.(d) Write the three most stable resonance contributors to the most stable enolate derived from ethyl (2-oxocyclohexane)carboxylate.(e) Show how you could use ethyl (2-oxocyclohexane)carboxylate to prepare 2-methylcyclohexanone.(f) Give the structure of the product formed on treatment of ethyl (2-oxocyclohexane)-carboxylate with acrolein (H2C=CHCH=O) in ethanol in the presence of sodium ethoxidearrow_forward
- Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict the major products of the reactions of naphthalene with the following reagents.(a) isobutylene and HF (b) cyclohexanol and BF3 (c) fuming sulfuric acidarrow_forwardPredict the products of reaction of pent-1-yne with the following reagents.(a) 1 equivalent of HCl (b) 2 equivalents of HCl (c) excess H2, Ni(d) H2, Pd>BaSO4, quinolinearrow_forward(a) How will you convert the following :(i) Propanone to Propan-2-ol (ii) Ethanal to 2-hydroxy propanoic acid(iii) Toluene to benzoic acid(b) Give simple chemical test to distinguish between :(i) Pentan-2-one and Pentan-3-one (ii) Ethanal and Propanalarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning