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(a)
Interpretation:
The reason for the opposite direction of the dipole moment of pyrrole and pyridine is to be stated.
Concept introduction:
Pyrrole is a five-membered cyclic
(b)
Interpretation:
The reason as to why pyrrole and furan have opposite direction of dipole moment is to be stated.
Concept introduction:
Pyrrole is a five-membered cyclic aromatic ring contains one nitrogen atom instead of a carbon atom. Similarly, furan is a five-membered cyclic aromatic ring contains one oxygen atom instead of a carbon atom. The dipole moment is used to measure the polarity of the bond in the molecule. It is defined as the product of the separation of charges and its magnitude. It is represented as shown below.
(c)
Interpretation:
Whether the dipole moment of
Concept introduction:
The dipole moment is used to measure the polarity of the bond in the molecule. It is defined as the product of the separation of charges and its magnitude. It is represented as shown below.
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Chapter 26 Solutions
EBK ORGANIC CHEMISTRY
- Each of the following is a much weaker base than aniline. Present a resonance argument to explain the effect of the substituent in each case. (a) o-Cyanoaniline (c) p-Aminoacetophenonearrow_forward(b) Give two suggestions of chemical modification of the below compound to make it more drug-like. NH H;N COH HN COHarrow_forwardGive reasons: (i) Bond length of C = O in carboxylic acids is slightly larger than C = O bond length in carbonyl compounds. (ii) There are two –NH2 groups in semicarbazide. However, only one –NH2 group is involved in the formation of semicarbazones. (iii) Benzoic acid is less soluble in water than acetic acid. (iv) Formic acid is a stronger acid than acetic acid.arrow_forward
- Without looking at a table of pKa data, rank the following compounds in order of increasing acidity. (a) Benzoic acid, p-methylbenzoic acid, p-chlorobenzoic acid (b) p-Nitrobenzoic acid, acetic acid, benzoic acid Explain in each case your choice for the highest acidity.arrow_forwardAnswer ALL parts of this question. (a) Using resonance structures, discuss the following statement; phenols are much stronger acids than aliphatic alcohols. (b) Give the structure of a stronger organic acid than phenol. (c) Rationalise the acidity of the latter organic acid by drawing two resonance structures of the conjugate base. (d) Eugenol is a natural product derived from the dried flower buds of the evergreen tree, Eugenia aromatica. Briefly describe a procedure with reagents required to extract eugenol as a single component from the mixture of compounds present in these flower buds. OH LOCH 3 eugenolarrow_forward(a) Give chemical tests to distinguish between the following pairs of compounds :(i) Pentan-2-ol and Pentan-3-ol (ii) Methanol and Phenol(b) o-nitro phenol is more acidic than o-methoxy phenol. Explain why.arrow_forward
- Illustrate the resonance effect of the methoxy group -OCH3, on the structure of the benzene ring. Draw all the oissuvke resonance forms of methoxybenzene, including the hybrid Based on the structures, explain how the presence of the -OCH3 group affects: (i) the reactivity of the benzene ring towards electrophilic attack (ii) the orientation or point of attack of an incoming electrophilic reagent on the benzene ring.arrow_forward(d) Ozonolysis of 3,4-dimethyl-3-hexene gives compound D. (i) Write the reaction step for the formation of D by including the appropriate reagents. (ii) The mass spectrum of compound D shows a fragment ion peak at m/z 57. Propose the structure of this fragment ion. (ii) Identify the more stable resonance of the proposed structure in (ii).arrow_forward(iii) State whether you think each of the molecules A to D below is aromatic, anti-aromatic, or non- aromatic. Note that only one resonance form of each compound is drawn. Give your reasoning in each case. NH A в D (iv) Sketch an energy profile for a typical electrophilic aromatic substitution reaction of benzene with an electrophile E*, showing the structures of the reactants, the intermediate and the products.arrow_forward
- (a) (b) Briefly explain why the alpha hydrogens of carbonyl compounds are much more acidic than typical C-H bonds, such as those in methane. Predict the structure of the product formed in the following reaction. Explain your reasoning. ن PPh3arrow_forward(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) Ph THF A Ph Ph B H₂SO4 100 °C 3 OH (iii) In analysing both these methods, are there other possible alkene products other than methylenecyclohexane 2? Use mechanistic details to support your answer.arrow_forward(a) Why are alkyl halides insoluble in water? (b) Why is Butan-l-ol optically inactive but Butan-2-ol is optically active? (c) Although chlorine is an electron withdrawing group, yet it is ortho-, Para- directing in electrophilic aromatic substitution reaction. Why?arrow_forward
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