Topic 10: Organic Chemistry P1:.. / 15p. P2:. / 29p.
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1 IB L EMISTRY Name: Topic 10: Organic hemistry P1:.. / 15p. P:. / 9p. 7: 35 6: 31 5: 6 4: 3: 18 : Which compound can exist as optical isomers? A. N OO B. 3 ON. 3 BrI D. OO 3. What is the organic product of the reaction between ethanol and ethanoic acid in the presence of sulfuric acid? A. 3 O B. 3 OO 3. 3 OO 3 D. 3 OO 3 3. What is the correct IUPA name for the following compound? N 3 A. 4-methylbutanenitrile B. 4-methylpentanenitrile. -methylbutanenitrile D. -methylpentanenitrile 3 4. What is the product of the following reaction? 3 N + Ni A. 3 N B D. 3 N 5. Propane, 3 8, undergoes incomplete combustion in a limited amount of air. Which products are most likely to be formed during this reaction? A. arbon monoxide and water B. arbon monoxide and hydrogen. arbon dioxide and hydrogen D. arbon dioxide and water 1
2 6. Which amino acid can exist as optical isomers? A. B.. D. 7. ow many chiral carbon atoms are present in a molecule of glucose? A. 1 B.. 3 D. 4
3 8. Nylon is a condensation polymer made up of hexanedioic acid and 1,6-diaminohexane. Which type of linkage is present in nylon? A. Amide B. Ester. Amine D. arboxyl 9. Which species reacts most readily with propane? A. Br B. Br. Br D. Br Which pair of compounds can be used to prepare 3 OO 3? A. Ethanol and methanoic acid B. Methanol and ethanoic acid. Ethanol and ethanoic acid D. Methanol and methanoic acid 11. Which compound forms when hydrogen bromide is added to but--ene? A. -bromobutane B.,3-dibromobutane. 1-bromobutane D. 1,-dibromobutane 1. The following is a three-dimensional representation of an organic molecule. Which statement is correct? A. The correct IUPA name of the molecule is -methylpentane. B. All the bond angles will be approximately 90.. One isomer of this molecule is pentane. D. The boiling point of this compound would be higher than that of pentane. 3
4 13. Which statement about successive members of all homologous series is correct? A. They have the same empirical formula. B. They differ by a group.. They have the same physical properties. D. They differ in their degree of unsaturation. 14. An organic compound X reacts with excess acidified potassium dichromate(vi) to form compound Y, which reacts with sodium carbonate to produce O (g). What is a possible formula for compound X? A. 3 OO B. 3 O. 3 (O) 3 D. ( 3 ) 3 O 15. Which compound is a tertiary halogenoalkane? A. ( 3 ) Br B. 3 ( ) 3 Br. ( 3 ) Br D. 3 ( 3 ) Br 16. The compound, -bromobutane, 3 Br 3, can react with sodium hydroxide to form compounds F, G and. ompound F, 4 10 O, exists as a pair of optical isomers. ompounds G and, 4 8, are structural isomers, and compound exists as a pair of geometrical isomers. (i) Draw the structures of the two optical isomers of F. 4
5 (ii) Outline the use of a polarimeter in distinguishing between the optical isomers. (iii) Draw diagrams to show the shapes of the two geometrical isomers of. (iv) Draw the mechanism, using curly arrows to represent the movement of electron pairs, to show the formation of G. (3) (Total 9 marks) 5
6 17. The molecular formula, 3 4 represents several isomeric compounds. Some isomers are cyclic and some are unsaturated. (a) Draw the structures of two cyclic compounds that are structural isomers and state the names of both isomers. (b) Two of the non-cyclic compounds have geometrical isomers. Draw the structures of these compounds and their geometrical isomers. (Total 4 marks) 18. (i) Identify the formulas of the organic products, A E, formed in the reactions, I IV: I. 3 ( ) 8 O + K r O 7 A B II. ( 3 ) 3 Br + NaO III. ( 3 ) O + K r O 7 D IV. = + Br E (5) 6
7 (ii) = can react to form a polymer. Name this type of polymer and draw the structural formula of a section of this polymer consisting of three repeating units. (Total 7 marks) 19. The following is a computer-generated representation of the molecule, methyl -hydroxy benzoate, better known as oil of wintergreen. (i) Deduce the empirical formula of methyl -hydroxy benzoate and draw the full structural formula, including any multiple bonds that may be present. The computer-generated representation shown does not distinguish between single and multiple bonds. 7
8 (ii) In this representation, two of the carbon-oxygen bond lengths shown are nm and nm. Explain why these are different and predict the carbon-oxygen bond length in carbon dioxide. (iii) Name all the functional groups present in the molecule. (Total 6 marks) 0. Polyesters are formed in a condensation reaction. The structure of the repeat unit of a polyester is O O O O (i) Draw the structures of the two monomers that react to form this polyester. (ii) Identify the essential feature of the monomers in (i) that enable them to form a condensation polymer. (1) (Total 3 marks) 8
9 1.. D 3. B 4. D 5. A 6. B 7. D 8. A 9. B 10. B 9
10 11. A B 14. B 15. D 16. (i) O O Award [] for both tetrahedral structures, or if tetrahedral structure is not clear. (ii) (iii) plane polarized light; rotation in opposite/different directions; 3 3 ; 3 3 ; (iv) curly arrow showing attack by O on end ; curly arrow showing Br bond fission; curly arrow showing formation of double bond; O and Br shown as products; Award each for any three. If but--ene formed, award [ max]. 3 max [9] 17. (a) and 1,1 dichlorocyclopropane; (cis- or trans-) 1, dichlorocyclopropane; Award point for the correct name corresponding to the related isomer. Accept diagrams that do not display 3 dimensional structure. Award [1 max] for correct structures only, without the corresponding names. 10
11 (b) 3 and 3 and [4] 18. (i) A. = 3 ( ) 7 O; B. = 3 ( ) 7 OO/ 3 ( ) 7 O ;. = ( 3 ) 3 O; D. = ( 3 ) O; E. = Br Br; 5 Allow correct structural formulas. (ii) addition; /-( - ) 3 -/-( ) 6 -; [7] 19. (i) (Empirical formula =) 8 8 O 3 ; O O O ; Allow double bonds on arene in alternate positions, or allow delocalized representation (of pi electrons). (ii) (iii) the bond at nm is a double bond and the bond at nm is a single bond; in O (g) both bonds are double bonds and would have a value around nm; Ester; Arene/benzene ring; Alcohol; Award for any three correct, award for any two correct. Do not accept alkane as a type of functional group in this molecule. [6] 0. (i) O O; OO 6 4 OO; (ii) reactants have two functional groups/owtte; 1 [3] 11
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ontaminant Behavior in the Environment: Basic Principles 41 opyright 2008. R Press All rights reserved. May not be reproduced in any form without permission from the publisher, except Depending on its
Polymers: Introduction
Chapter Outline: Polymer Structures Hydrocarbon and Polymer Molecules Chemistry of Polymer Molecules Molecular Weight and Shape Molecular Structure and Configurations Copolymers Polymer Crystals Optional
ORGANIC NOMENCLATURE
hemistry 121 Winter 2001 ourse otes Principles of hemistry II Introduction RGAI MELATURE onfusion can arise in organic chemistry because of the variety of names that have been applied to compounds; common
for excitation to occur, there must be an exact match between the frequency of the applied radiation and the frequency of the vibration
! = 1 2"c k (m + M) m M wavenumbers! =!/c = 1/" wavelength frequency! units: cm 1 for excitation to occur, there must be an exact match between the frequency of the applied radiation and the frequency
Molecular Structures. Chapter 9 Molecular Structures. Using Molecular Models. Using Molecular Models. C 2 H 6 O structural isomers: .. H C C O..
John W. Moore onrad L. Stanitski Peter. Jurs http://academic.cengage.com/chemistry/moore hapter 9 Molecular Structures Stephen. oster Mississippi State University Molecular Structures 2 6 structural isomers:
The Four Questions to Ask While Interpreting Spectra. 1. How many different environments are there?
1 H NMR Spectroscopy (#1c) The technique of 1 H NMR spectroscopy is central to organic chemistry and other fields involving analysis of organic chemicals, such as forensics and environmental science. It
Name of mechanism...... (1) For Step 3, give the reagent, give a necessary condition and name the mechanism. Reagent... Condition...
Q. A possible synthesis of the amino acid X is shown below. (a) Name and outline a mechanism for Step. Name of mechanism... Mechanism (5) (b) Give the IUPAC name of the product of Step.... () (c) For Step,
AROMATIC COMPOUNDS A STUDENT SHOULD BE ABLE TO:
A STUDENT SHULD BE ABLE T: ARMATIC CMPUNDS 1. Name benzene derivatives given the structures, and draw the structures given the names. This includes: Monosubstituted benzenes named as derivatives of benzene: