a) p-Nitroaniline, p-aminobenzaldehyde, p-bromoaniline
Interpretation:
The compounds p-nitroaniline, p-aminobenzaldehyde and p-bromoaniline are to be arranged in the increasing order of their basicity.
Concept introduction:
b) p-Chloroaniline, p-aminoacetophenone, p-methylaniline
Interpretation:
The compounds p-chloroaniline, p-aminoacetophenone and p-methylaniline are to be arranged in the increasing order of their basicity.
Concept introduction:
Amines are basic as they can donate the lone pair if electrons on the N atom. Generally aryl amines are less basic than alkyl amines. An electron withdrawing substituent present on the aromatic ring reduces the base strength while an electron releasing substituent present on the aromatic ring enhances the base strength.
c) p-(trifluoromethyl)aniline, p-methylaniline, p-(fluoromethyl)aniline
Interpretation:
The compounds p-(trifluoromethyl)aniline, p-methylaniline and p-(fluoromethyl) aniline are to be arranged in the increasing order of their basicity.
Concept introduction:
Amines are basic as they can donate the lone pair if electrons on the N atom. Generally aryl amines are less basic than alkyl amines. An electron withdrawing substituent present on the aromatic ring reduces the base strength while an electron releasing substituent present on the aromatic ring enhances the base strength.
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Chapter 24 Solutions
Organic Chemistry
- Although acetanilide and phenacetin are not appreciably acidic, aceta- minophen (like aspirin) is a stronger acid than water. What problem would you encounter if the unknown component were acetaminophen rather than acetanilide or phenacetin, and you extracted the aspirin with 5% NaOH? Explain, giving equations for any relevant reactions.arrow_forward11. Which compound is the strongest base? (A) m-nitroaniline (B) aniline (C) 4-methylaniline (D) 3-bromo-5-nitroaniline (E) 2,4-dimethylaniline 13 Which of the following compounds has the 12. Which compound is the strongest acid? (A) benzoic acid (B) 4-amino-2-methylbenzoic acid (C) p-nitrobenzoic acid (D) 2,4-dinitroabenzamide (E) 3,5-dinitrobenzoic acid 14 How many H atoms are in the compound:arrow_forwardThe –NHCOR group of an amide is an activating group, but it is not as strongly activating as NH2. (a) Explain why it is an activating group. (b) Explain why it is less activating than NH2.arrow_forward
- Histamine, whose release in the body triggers nasal secretions and constricted airways, has three nitrogen atoms. List them in order of increasing basicity and explain your ordering.arrow_forwardDraw a structural formula for each amine and amine derivative. (a) N,N-Dimethylaniline (b) Triethylamine (c) tert-Butylamine (d) 1,4-Benzenediamine (e) 4-Aminobutanoic acid (f) (R)-2-Butanamine (g) Benzylamine (h) trans-2-Aminocyclohexanol (i) 1-Phenyl-2-propanamine (amphetamine) (j) Lithium diisopropylamide (LDA) (k) Benzyltrimethylammonium hydroxide (Triton B)arrow_forwardi) What property of amines is responsible for their being basic ii) Arrange the following compounds in order of increasing basic strength putting the least basic first. NH3 CH,CONH; O NH2 CH,CH;NH; D C. c) What general name is given to the reaction between phenylamine and nitrous acid at 5°C ii) Write the equation for the reaction in c(i). + Ajouter une légende.. > Statut (Personnalisé)arrow_forward
- Give answer all questions with explanationarrow_forwardArrange each group of compounds in order of increasing basicity.(a) CH3COO-, ClCH2COO-, and PhO- (b) sodium acetylide, sodium amide, and sodium acetate(c) sodium benzoate, sodium ethoxide, and sodium phenoxide (d) pyridine, sodium ethoxide, and sodium acetatearrow_forward(a) Explain how NaBH, in CH;OH can reduce hemiacetal A to 1,4-butanediol (HOCH,CH,CH,CH,OH). (b) What product is formed when A is treated with Ph;P=CHCH,CH(CH),? (c) The drug isotretinoin is formed by reaction of X and Y. What is the structure of isotretinoin? Although isotretinoin (trade name Accutane or Roaccutane) is used for the treatment of severe acne, it is dispensed under strict controls because it also causes birth defects. PPha NaOCH,CH3 HO- isotretinoin HO A Br X Yarrow_forward
- Arrange each group of compounds in order of increasing acidity.(c) benzoic acid, o-nitrobenzoic acid, m-nitrobenzoic acidarrow_forwardWhich is the stronger acid in each of the following pairs? Explain your reasoning. (a) Phenol or p-hydroxybenzaldehyde (b) m-Cyanophenol or p-cyanophenol (c) o-Fluorophenol or p-fluorophenolarrow_forwardShow how acid derivatives hydrolyze to carboxylic acids under either acidic or basicconditions. Explain why some acid derivatives (amides, for example) require muchstronger conditions for hydrolysis than other derivatives.arrow_forward
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning