10.Carboxylic Acid and Derivatives - Student Copy

pdf

School

Nanyang Technological University *

*We aren’t endorsed by this school

Course

MISC

Subject

Chemistry

Date

Nov 24, 2024

Type

pdf

Pages

7

Uploaded by CaptainGalaxyTapir10

Report
YISHUN INNOVA JUNIOR COLLEGE 2021 JC2 H2 CHEMISTRY CARBOXYLIC ACID AND DERIVATIVES (FOUNDATION) DHS/2020/I/24 1 An ester has the structure shown. Which two compounds will react together to form this ester? 1 3 methylbutanoic acid 2 2 methylbutanoyl chloride 3 pentan 2 ol 4 2 methylbutan 1 ol A 1 and 3 C 2 and 3 B 1 and 4 D 2 and 4 NYJC/2020/I/27 2 Use of the Data Booklet is relevant to this question. A sample of ethyl propanoate is hydrolysed by heating under reflux with aqueous sodium hydroxide. The two organic products of the hydrolysis are separated, purified and weighed. Out of the total mass of products obtained, what is the percentage by mass of each product? A 32.4 % and 67.6 % B 38.3 % and 61.7 % C 41.5 % and 58.5 % D 42.3 % and 57.7 % O O
SAJC/2020/I/26 3 Diester T has the molecular formula C 7 H 12 O 4 . One of the products from acid hydrolysis of T produces no effervescence when heated with acidified KMnO 4 (aq). Which of the following structures can be compound T ? A CH 3 CO 2 CH 2 CH 2 OCOCH 2 CH 3 B CH 3 CH 2 CO 2 CH 2 CO 2 CH 2 CH 3 C CH 3 OCOCH 2 CH 2 CO 2 CH 2 CH 3 D CH 3 CH 2 OCOCH 2 CO 2 CH 2 CH 3 TMJC/2020/I/28 4 The synthesis of nitrobenzene derivatives is shown below. O 2 N NO 2 O 2 N NO 2 O 2 N O 2 N OCH 3 O 2 N N H 2 OCH 3 O 2 N NH OCH 3 O 2 N C O C H 2 CH 3 I II III Which set of reagents and conditions can be used for the synthesis? Stage I Stage II Stage III A conc. HNO 3 and conc. H 2 SO 4 LiA l H 4 in dry ether CH 3 CH 2 COC l B conc. HNO 3 Sn in conc. HC l CH 3 CH 2 COOH C conc. HNO 3 and conc. H 2 SO 4 Sn in conc. HC l CH 3 CH 2 COC l D dilute HNO 3 H 2 with Ni catalyst CH 3 CH 2 COOH
TJC/2020/III/4b, c 5 (a) Explain why 3-chlorobenzoic acid is sparingly soluble in water but 3-chloropropanoic acid is soluble in water. [2] (b) Explain the relative acidities for the following sets of organic acids. (i) 3-chloro-4-hydroxybenzoic acid 3-chloro-2-hydroxybenzoic acid [1] (ii) 2-chlorobutanoic acid, 4-chlorobutanoic acid and 4-bromobutanoic acid [2] DHS/2020/II/3a, b 6 (a) Acidic solutions of different pH were formed when one mole of each of the following compounds was dissolved in 1.0 dm 3 of water separately. O OH Cl chloroethanoic acid O OH ethanoic acid O Cl ethanoyl chloride Arrange the three acidic solutions formed in order of increasing pH and explain your reasoning. [3] (b) When an aqueous solution of silver nitrate was added to ethanoyl chloride and chloroethane, a white precipitate was observed immediately for one of the compounds. Identify the compound that gives the white precipitate and account for the difference in the reactivities. [2]
Your preview ends here
Eager to read complete document? Join bartleby learn and gain access to the full version
  • Access to all documents
  • Unlimited textbook solutions
  • 24/7 expert homework help
HCI/2020/II/2c 7 Wine contains a mixture of organic acids, such as tartaric acid and malic acid. These acids produce a prickling sensation on the tongue during wine-tasting. malic acid tartaric acid Which of the two acids has a lower pK a1 ? Explain. [2] ACJC/2020/III/5d 8 Draw the structure of the ester formed between propanoic acid and butan-2-ol and state the reagents and conditions required for this conversion. [2] TJC/2020/III/2b 9 Describe and explain the relative ease of hydrolysis of compounds P , Q and S . compound P compound Q compound S [3] CH 2 CH 2 C l CH 2 COC l CH 2 CH 2 Br
YISHUN INNOVA JUNIOR COLLEGE 2021 JC2 H2 CHEMISTRY CARBOXYLIC ACID AND DERIVATIVES (ADVANCED) VJC/2020/I/24 10 Which of the following statements is correct about compound Z ? compound Z A A molecule of Z contains 8 sp 2 hybridised carbon atoms. B Z undergoes a condensation reaction with aqueous ammonia to give an amide C 1 mol of Z produced 3 mol of hydrogen gas when reacted with excess sodium. D A molecule of Z can incorporate up to 4 bromine atoms when reacted with aqueous bromine RI/2020/II/4g, h 11 Fig. 4.5 shows the conversion of acetoin into oxalyl chloride, C 2 O 2 C l 2 , via a series of reactions. Fig. 4.5 (a) (i) Draw the structures of T and oxalyl chloride. [2] (ii) Suggest the reagents and conditions for step 1. [1] (b) Oxalyl chloride reacts with reagent U in a 1:1 mole ratio as shown below. Suggest the identity of U .
NYJC/2020/II/4a, b 12 The Claisen condensation occurs between two esters in the presence of a strong base to produce a keto ester and an alcohol. 1. NaOR' 2. H 3 O + + CH 2 C O O R' R CH 2 C O O R' R CH 2 C O CH C R R O O R' + R'OH ester 1 ester 2 keto ester alcohol An example of this reaction involving two ethyl ethanoate, with sodium ethoxide as the base, is shown below. + 1. NaOCH 2 CH 3 2. H 3 O + O O O O O O O OH + For this reaction to occur, at least one of the reactants must have an α -hydrogen atom. The α -hydrogen atom is the hydrogen atom attached to the first carbon atom beside the carbonyl carbon atom. In the first step, this α -hydrogen atom is removed by a strong base, such as an alkoxide, resulting in the formation of an enolate anion. step I NaOR' CH 2 C O O R' R CH C O O R' R - .. enolate anion step II CH 2 C O O R' R CH 2 C O CH C R R O O R' + R'O - CH C O O R' R - .. enolate anion keto ester (a) (i) Suggest a reason why the α -hydrogen atom of the ester is acidic. [1] (ii) NaOH(aq) is not used as a strong base in step I to remove the α -hydrogen atom because it will react with the ester instead. Explain how NaOH reacts with the ester. [1] (iii) State the type of reaction between the ester and the enolate anion in the second step. [1] (iv) When two different esters are used as reactants in the Claisen condensation, a mixture of four different keto esters can be formed. Suggest the structures of three possible keto esters produced when a mixture of ethyl ethanoate, CH 3 CO 2 CH 2 CH 3 , and ethyl propanoate, CH 3 CH 2 CO 2 CH 2 CH 3 , is used. [2]
Your preview ends here
Eager to read complete document? Join bartleby learn and gain access to the full version
  • Access to all documents
  • Unlimited textbook solutions
  • 24/7 expert homework help
(v) Suggest the structure of compound A . [1] (b) The Claisen condensation can also occur between a ketone and an ester. An α -hydrogen atom in the ketone is first removed by the strong base, and the subsequent reaction with the ester can then take place with the same mechanism described in part (a) . Cyclohexanone reacts with one mole of compound P to produce compound Q and ethanol in the Claisen condensation. O + P Q (C 10 H 14 O 4 ) cyclohexanone 1. NaOCH 2 CH 3 2. H 3 O + + CH 3 CH 2 OH Upon heating compound Q with dilute sulfuric acid, compound R (C 8 H 10 O 4 ) is obtained. Compound R gives an orange precipitate with 2,4-DNPH, but no silver mirror was observed with Tollen’s reagent. When compound R is heated with acidified K 2 Cr 2 O 7 , the orange solution remained. Effervescence was observed when solid Na 2 CO 3 was added to compound R . Suggest the structures of P , Q and R and explain the chemistry of the reactions occurred. [5] O O O OH + 1. NaOCH 2 CH 3 2. H 3 O + A