Interpretation:
The steps for acid and base catalyzed reactions involved in
Concept introduction:
The reaction of water with acetone can take place under acidic or basic conditions.
Water reacts with acetone to form gem
Electrophiles are electron deficient species, which has positive or partially positive charge. Lewis acids are electrophiles, which accept electron pair.
Nucleophiles are electron rich species, which has negative or partially negative charge. Lewis bases are nucleophiles, which donate electron pair.
Acceleration of
Acceleration of chemical reaction by addition of base, without being consumed in the reaction is called base catalyzed reaction.
Want to see the full answer?
Check out a sample textbook solutionChapter 16 Solutions
Organic Chemistry
- Low-molecular-weight dicarboxylic acids normally exhibit two different pK, values. Ionization of the first carboxyl group is easier than the second. This effect diminishes with molecular size, and for adipic acid and longer chain dicarboxylic acids, the two acid ionization constants differ by about one pK unit. Dicarboxylic Acid Structural Formula pK,2 a1 Охalic НООССООН 1.23 4.19 Malonic НООСCH,COOH 2.83 5.69 Succinic HOOC(CH,),COOH 4.16 5.61 Glutaric HOOC(CH,),COOH 4.31 5.41 Adipic HOOC(CH,),COOH 4.43 5.41 Why do the two pK, values differ more for the shorter chain dicarboxylic acids than for the longer chain dicarboxylic acids?arrow_forwardSelect a reagent to separate the following compounds (one reagent only) (explain clearly what happened to each compound in the mixture) AgCl and PbCl2 and NaCl Hg and AgCl PbSO4 and PbCO3 Hg2(NO3)2 and Pb(NO3)2arrow_forwardDetergent is a cleaning agent that is widely used in various purposes. One type of detergent is anionic detergent which is generally a sodium salt of a sulfonic acid such as sodium dodecylbenzene sulphonate. Write the correct reagent (not synthone) for I-IV ! The correct sodium dodecylbenzene sulphonate disconnection strategy is through pathway a or b ?arrow_forward
- 2) Draw curved arrows to represent the flow of electrons during the following reaction CH,0 + CH,OH + :CI:arrow_forwarda) b) C) HBr CH3CH₂OOCH₂CH3 1. Hg(OAc)2, H₂O 2. NaBH4 1) BH₂ / THF 2) H₂O2 NaOH (aq) coldarrow_forwardb) If you treat either A or B with the same reagents, you obtain the same major product. Explain why this is the case by depicting any relevant intermediates and/or using a written description A 1) NaH Br 2) acid (H3O+), heat 1) NaH Br 2) acid (H3O+), heat Barrow_forward
- Arrange the following compound in the order of increasing acidity (least acidic first) I) Cyclohexanol II) 4-Nitrophenol III) Phenol IV) 4-Chlorophenol O I, III, IV, II O I, II, III, IV O III, IV, II, I O II, I, IV, IIIarrow_forwardThe ionization of p-nitrophenol is shown below (pKa= 7.0) a) At pH 7, what are the relative concentrations of ionized and un-ionized p-nitrophenol? b) If enough concentrated hydrochloric acid is added to a solution of p-nitrophenol to lower the pH from 7 to 5, what will happen to the relative concentrations of the ionized and un-ionized forms? c) A solution of p-nitrophenol at pH 8.3 was found to have an A400 of 0.550. What is the total concentration (in um) of p-nitrophenol (ionized plus un-ionized) in the solution? The molar extinction coefficient of p-nitrophenol is 19,500M-1cm-1 and the pKa is 7.arrow_forwardAnswer questions a-c about the Bronsted acid-base reaction below using the identifying letters A-D below each structure. The pKa's for the acids of interest are: ammonia (pK, = 36), and acetone (pK, = 19.3). "NH2 CH CH3 NH3 CH3 A D acetone enolate amide acetone ammonia a) The stronger acid is b) Its conjugate base is c) The species that predominate at equilibrium are (two letters, e.g. ac)arrow_forward
- 4. The following two compounds are protonated when treated with one mole equivalent of a strong acid (e.g. HCI). For each compound, draw the equilibrium to show the preferred site of protonation and give an estimate of the base strength (pKaH). -OHarrow_forward8. What is the order of increasing acidity for the following compounds? Br I CH3CH₂COOH BrCH₂CH₂COOH CH3CH₂CH₂OH CH3CHCOOH I IV, II, I, III I, II, IV, III c. III, I, II, IV d. III, IV, II, I e. I, II, III, IV a. b. II III IVarrow_forward4 5 Arrange the following bases in increasing base strength. There is no partial credit on this problem. Weakest base 1 2 3 Pyridine (C5H5N), Kb = 1.7 x 10-⁹ Aniline (C6H5NH2), Kb = 3.9 x 10-10 Strongest base Methylamine (CH3NH₂), Kb = 4.4 x 10-4 Hydrazine (N2H4), Kb = 1.3 x 10-6 ⠀ Dimethylamine ((CH3)2NH), K₂ = 5.1 x 10-4arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning