2. New Way Chemistry for Hong Kong A-Level Book 3A1 1 R, R’ = alkyl groups with 4-15 carbon atoms 鄰苯二甲酸酯 (phthalate ester) PAE benzoic acid ( 苯甲酸 )

3. New Way Chemistry for Hong Kong A-Level Book 3A2 2 R, R’ = alkyl groups with 4-15 carbon atoms 鄰苯二甲酸酯 (phthalate ester) Used as plasticiser Potential carcinogen New car smell ortho-phthalic acid benzene-1,2-dicarboxylic acid ( 鄰苯二甲酸 )

4. New Way Chemistry for Hong Kong A-Level Book 3A3 3 鄰苯二甲酸酯 (phthalate ester) Used as plasticiser Potential carcinogen Endocrine disruption New car smell

5. New Way Chemistry for Hong Kong A-Level Book 3A4 4 dibutyl benzene-1,2-dicarboxylate butyl pentyl benzene-1,2-dicarboxylate space

6. New Way Chemistry for Hong Kong A-Level Book 3A5 5 isophthalic acid meta-phthalic acid 間苯二甲酸 terephthalic acid para-phthalic acid 對苯二甲酸 benzene-1,3- dicarboxylic acid benzene-1,4- dicarboxylic acid

7. New Way Chemistry for Hong Kong A-Level Book 3A6 polyester Ester linkage (terylene)

8. New Way Chemistry for Hong Kong A-Level Book 3A7 Polyethylene terephthalate PET or PETE CH 2 CH 2 = ethene = ethylene

9. New Way Chemistry for Hong Kong A-Level Book 3A8 8 Isomerism

10. 9 9 Isomerism Compounds having the same molecular formula but different linkages or spatial arrangements of atoms Occurs when certain compounds, having the same molecular formula, exist in different forms. Isomers

11. New Way Chemistry for Hong Kong A-Level Book 3A10 Two main types of isomerism: 1.Structural isomerism – different linkages of atoms. 2.Stereoisomerism –different spatial arrangements of atoms Isomerism

12. New Way Chemistry for Hong Kong A-Level Book 3A11 Two main types of isomerism: 1.Structural isomerism – different linkages of atoms. Isomerism Same molecular formula Different structural formulae

13. New Way Chemistry for Hong Kong A-Level Book 3A12 2.Stereoisomerism –different spatial arrangements of atoms Isomerism Same molecular formula & structural formulae

14. New Way Chemistry for Hong Kong A-Level Book 3A13 Categories of Isomerism Optical isomerism p.24

15. New Way Chemistry for Hong Kong A-Level Book 3A14 Categories of Isomerism Optical isomerism Diastereoisomerism Stereoisomerism Geometrical isomerism Enantiomerism Optical isomers that are NOT mirror images of each other Optical isomers that are mirror images of each other

16. New Way Chemistry for Hong Kong A-Level Book 3A15 Structural Isomerism

17. New Way Chemistry for Hong Kong A-Level Book 3A16 1. Chain isomerism due to the presence of different carbon skeletons.

18. New Way Chemistry for Hong Kong A-Level Book 3A17 1. Chain isomerism C 6 H 14 p.2, Q.2

19. New Way Chemistry for Hong Kong A-Level Book 3A18 1. Chain isomerism Different physical properties b.p.:Straight-chain > branched-chain Reason : - larger surface area and thus stronger v.d.w. forces >

20. New Way Chemistry for Hong Kong A-Level Book 3A19 1. Chain isomerism Different physical properties -20°C-136°C > m.p.:Symmetry of molecule   Packing efficiency   m.p. 

21. New Way Chemistry for Hong Kong A-Level Book 3A20 1. Chain isomerism Different physical properties -20°C-136°C > Notes on ‘Bonding and Structure’ p.81, Q.61

22. New Way Chemistry for Hong Kong A-Level Book 3A21 Chain isomers have different physical properties. What about their chemical properties? Would they be different as well? Chain isomers have similar chemical properties because they have the same functional groups.

23. New Way Chemistry for Hong Kong A-Level Book 3A22 2. Position isomerism Same carbon skeleton Different positions of functional groups

24. New Way Chemistry for Hong Kong A-Level Book 3A23 2. Position isomerism e.g.Butan-1-ol and butan-2-ol (molecular formula: C 4 H 10 O)

25. New Way Chemistry for Hong Kong A-Level Book 3A24 Wrong ! Q.15 Are they position isomers ? They are chain isomers

26. New Way Chemistry for Hong Kong A-Level Book 3A25 3. Functional Group Isomerism Due to the presence of different functional groups

27. New Way Chemistry for Hong Kong A-Level Book 3A26 Functional Group Isomerism AlcoholEtherVs C2H6OC2H6O

28. New Way Chemistry for Hong Kong A-Level Book 3A27 Functional Group Isomerism AldehydeKetoneVs C3H6OC3H6O

29. New Way Chemistry for Hong Kong A-Level Book 3A28 Functional Group Isomerism Carboxylic acidEsterVs C3H6O2C3H6O2

30. New Way Chemistry for Hong Kong A-Level Book 3A29 Position isomers Chain isomers C 5 H 10

31. New Way Chemistry for Hong Kong A-Level Book 3A30 Functional group isomers

32. New Way Chemistry for Hong Kong A-Level Book 3A31 4. Metamerism Occurs when the functional group (-oxy or –carbonyl) interrupts the main carbon skeleton at different positions

33. New Way Chemistry for Hong Kong A-Level Book 3A32 4. Metamerism e.g.Methoxypropane and ethoxyethane (molecular formula: C 4 H 10 O)

34. New Way Chemistry for Hong Kong A-Level Book 3A33 4. Metamerism e.g.Pentan-2-one and pentan-3-one (molecular formula: C 5 H 10 O) can also be considered as position isomers

35. New Way Chemistry for Hong Kong A-Level Book 3A34 Position isomers Chain isomers C 4 H 10 O

36. New Way Chemistry for Hong Kong A-Level Book 3A35 Position isomers Metamers functional group isomers C 4 H 10 O

37. New Way Chemistry for Hong Kong A-Level Book 3A36 5. Tautomerism Occurs when functional group isomers are in dynamic equilibrium with each other.

38. New Way Chemistry for Hong Kong A-Level Book 3A37 5. Tautomerism ethenol ethanal enol – keto tautomerism

39. New Way Chemistry for Hong Kong A-Level Book 3A38 5. Tautomerism ethenol ethanal Enol is a structure with –OH attached directly to doubly-bonded C

40. New Way Chemistry for Hong Kong A-Level Book 3A39 5. Tautomerism Not an enol But-2-en-1-ol Does not exhibit tautomerism

41. New Way Chemistry for Hong Kong A-Level Book 3A40 Which one, the enol form or the keto form, is the stronger acid ? The enol form is the stronger acid because the H attached to the more electronegative O can be released as H + more easily. Q.16

42. New Way Chemistry for Hong Kong A-Level Book 3A41 More stableLess stable More stable The equilibrium position lies to the right stronger acid weaker acid Q.16

43. New Way Chemistry for Hong Kong A-Level Book 3A42 Stereoisomerism

44. New Way Chemistry for Hong Kong A-Level Book 3A43 Stereoisomerism occurs when compounds having the same structural formula show different spatial arrangements of atoms.

45. New Way Chemistry for Hong Kong A-Level Book 3A44 Stereoisomerism Two categories of stereoisomerism: 1.Geometrical isomerism 2.Optical isomerism

46. New Way Chemistry for Hong Kong A-Level Book 3A45 Geometrical Isomerism arises from restricted rotation about a C=C double bond. Stereoisomerism

47. New Way Chemistry for Hong Kong A-Level Book 3A46 cannot be inter-converted at lower temperatures

48. New Way Chemistry for Hong Kong A-Level Book 3A47 Rotation about the axis of a double bond through an angle of 90 o results in the breaking of the π bond maximum overlap of p z orbitals minimum overlap of p z orbitals

49. New Way Chemistry for Hong Kong A-Level Book 3A48 Geometrical Isomerism - Criteria where a  b and c  d

50. New Way Chemistry for Hong Kong A-Level Book 3A49 E/Z notation If there are three or four different groups attached to the Cs of C=C double bond E/Z notation rather than the cis/trans notation is used to name the stereoisomers of a molecule. E : in opposition to  trans Z : together  cis http://en.wikipedia.org/wiki/Cahn-Ingold-Prelog_priority_rule

51. New Way Chemistry for Hong Kong A-Level Book 3A50 Q.17 Rotate the molecular plane w.r.t. the axis by 180  180  The same a = b

52. New Way Chemistry for Hong Kong A-Level Book 3A51 Q.17 180  The same a = b and c = d

53. New Way Chemistry for Hong Kong A-Level Book 3A52 Properties of Geometrical Isomers They have significantly different physical properties m.p.  80  C  50  C b.p. 60  C 48  C 1.

54. New Way Chemistry for Hong Kong A-Level Book 3A53 Zero net dipole moment van der Waals’ forces : cis > trans b.p. depends on v.d.w. forces ONLY  b.p. : cis > trans

55. New Way Chemistry for Hong Kong A-Level Book 3A54 more symmetrical less symmetrical Two planes of symmetry Three planes of symmetry

56. New Way Chemistry for Hong Kong A-Level Book 3A55 more symmetrical less symmetrical m.p. is more affected by symmetry of molecules.  m.p. : trans > cis higher packing efficiency lower packing efficiency

57. New Way Chemistry for Hong Kong A-Level Book 3A56 2. m.p. 130  C << 290  C

58. New Way Chemistry for Hong Kong A-Level Book 3A57 less extensive intermolecular hydrogen bond intra-molecular hydrogen bond

59. New Way Chemistry for Hong Kong A-Level Book 3A58 less extensive intermolecular hydrogen bond weaker v.d.w. forces + lower packing efficiency  much lower m.p.

60. New Way Chemistry for Hong Kong A-Level Book 3A59 Some geometrical isomers exhibit significantly different chemical properties 1. K 1 1.4  10  2 mol dm  3 >> 9.3  10  5 mol dm  3 K 2 8.0  10  7 mol dm  3 < 3.6  10  5 mol dm  3

61. New Way Chemistry for Hong Kong A-Level Book 3A60 Formation of intra-molecular hydrogen bond helps to draw electrons from the –OH  Weakening O – H  Ease of release of H +  H+H+  K 1 : cis > trans

62. New Way Chemistry for Hong Kong A-Level Book 3A61 In other words, the conjugate base is stabilized Furthermore, the -ve charge produced is stabilized by forming intra-molecular hydrogen bond. K 1 : cis >> trans

63. New Way Chemistry for Hong Kong A-Level Book 3A62 significant repulsionrepulsion is minimized K 2 : trans >> cis

64. New Way Chemistry for Hong Kong A-Level Book 3A63 Solubility in water (gram of solute per 100 g of water at 25°C) 78.8 0.7 Intra-molecular hydrogen bonds in cis-isomer reduce the extent of formation of intermolecular hydrogen bonds. Thus, water molecules can separate the acid molecules of the cis-isomer more easily  solubility of the cis-isomer in water is higher Q.18

65. New Way Chemistry for Hong Kong A-Level Book 3A64 2.Thermal dehydration of butenedioic acid 150°C250°C -H 2 O 250°C breaking and forming of  bond by rotating by 180° about the axis of the C=C double bond

66. New Way Chemistry for Hong Kong A-Level Book 3A65 plane-polarized light Light vibrating in ALL possible planes Light vibrating in only ONE plane

67. New Way Chemistry for Hong Kong A-Level Book 3A66 Optically active Optically active substance can rotate the plane of polarization of plane-polarized light Measured by a polarimeter.

68. New Way Chemistry for Hong Kong A-Level Book 3A67 Optically active Dextrorotatory(+) : clockwise (to the right) Laevorotatory(-): anti-clockwise (to the left) Is the above sample dextrorotatory ? No. It is laevorotatory

69. New Way Chemistry for Hong Kong A-Level Book 3A68 Optical activity arises from lack of symmetry asymmetry ( 不對稱 ) chirality ( 手性 ) E.g.A molecule with an sp 3 carbon atom bonded to FOUR different groups

70. New Way Chemistry for Hong Kong A-Level Book 3A69 The molecule has no plane or axis or center of symmetry.  It is asymmetric

71. New Way Chemistry for Hong Kong A-Level Book 3A70 It is not superimposable with its mirror image  It exhibits chirality mirror

72. New Way Chemistry for Hong Kong A-Level Book 3A71

73. New Way Chemistry for Hong Kong A-Level Book 3A72 Enantiomers ( 對映異構體 ) Mirror images of each other Non-superimposable with each other Rotate plane-polarized light to the same extent but in opposite directions

74. New Way Chemistry for Hong Kong A-Level Book 3A73 Enantiomers ( 對映異構體 ) The direction of optical rotation cannot be predicted from the structural formulae. It can only be determined experimentally.

75. New Way Chemistry for Hong Kong A-Level Book 3A74 Enantiomers ( 對映異構體 ) (+) or (-)butan-2-ol

76. New Way Chemistry for Hong Kong A-Level Book 3A75 ** *C is known as the chiral center or asymmetric centre Animation

77. New Way Chemistry for Hong Kong A-Level Book 3A76 Q.19Indicate the asymmetric carbon atom(s) in each of the following molecules. Which of them is/are optically active ? sp 3 hybridized C atoms each bonded to THREE identical H atoms  Not asymmetric

78. New Way Chemistry for Hong Kong A-Level Book 3A77 sp 2 hybridized C atoms are NOT chiral centers Q.19Indicate the asymmetric carbon atom(s) in each of the following molecules. Which of them is/are optically active ?

79. New Way Chemistry for Hong Kong A-Level Book 3A78 The molecule can be cut into two identical halves by the molecular plane It has a plane of symmetry It is NOT asymmetric Q.19Indicate the asymmetric carbon atom(s) in each of the following molecules. Which of them is/are optically active ?

80. New Way Chemistry for Hong Kong A-Level Book 3A79 sp 3 hybridized C atom bonded to three identical H atoms  Not asymmetric Q.19Indicate the asymmetric carbon atom(s) in each of the following molecules. Which of them is/are optically active ?

81. New Way Chemistry for Hong Kong A-Level Book 3A80 sp 3 hybridized C atom bonded to two identical Br atoms  Not chiral Q.19Indicate the asymmetric carbon atom(s) in each of the following molecules. Which of them is/are optically active ?

82. New Way Chemistry for Hong Kong A-Level Book 3A81 sp 3 hybridized C atom bonded to two identical H atoms  Not chiral Q.19Indicate the asymmetric carbon atom(s) in each of the following molecules. Which of them is/are optically active ?

83. New Way Chemistry for Hong Kong A-Level Book 3A82 sp 3 hybridized C atom bonded to two identical H atoms  Not chiral Q.19Indicate the asymmetric carbon atom(s) in each of the following molecules. Which of them is/are optically active ?

84. New Way Chemistry for Hong Kong A-Level Book 3A83 sp 3 hybridized C atoms bonded to three identical H atoms  Not chiral Q.19Indicate the asymmetric carbon atom(s) in each of the following molecules. Which of them is/are optically active ?

85. New Way Chemistry for Hong Kong A-Level Book 3A84 sp 3 hybridized C atom bonded to two identical CH 3 groups  Not chiral Q.19Indicate the asymmetric carbon atom(s) in each of the following molecules. Which of them is/are optically active ?

86. New Way Chemistry for Hong Kong A-Level Book 3A85 bromo ethyl (1-bromoisopropyl) H Q.19Indicate the asymmetric carbon atom(s) in each of the following molecules. Which of them is/are optically active ?

87. New Way Chemistry for Hong Kong A-Level Book 3A86 sp 3 hybridized C atom bonded to four different groups * Asymmetric Optically active (+) or (-) Q.19Indicate the asymmetric carbon atom(s) in each of the following molecules. Which of them is/are optically active ?

88. New Way Chemistry for Hong Kong A-Level Book 3A87 sp 3 hybridized C atoms bonded to three identical H atoms  Not chiral Q.19Indicate the asymmetric carbon atom(s) in each of the following molecules. Which of them is/are optically active ?

89. New Way Chemistry for Hong Kong A-Level Book 3A88 sp 3 hybridized C atoms bonded to four different groups Q.19Indicate the asymmetric carbon atom(s) in each of the following molecules. Which of them is/are optically active ?

90. New Way Chemistry for Hong Kong A-Level Book 3A89 H methyl hydroxy (1-hydroxyethyl) Q.19Indicate the asymmetric carbon atom(s) in each of the following molecules. Which of them is/are optically active ?

91. New Way Chemistry for Hong Kong A-Level Book 3A90 H methyl hydroxy (1-hydroxyethyl) Q.19Indicate the asymmetric carbon atom(s) in each of the following molecules. Which of them is/are optically active ?

92. New Way Chemistry for Hong Kong A-Level Book 3A91 * * Two chiral centers but optically inactive Q.19Indicate the asymmetric carbon atom(s) in each of the following molecules. Which of them is/are optically active ?

93. New Way Chemistry for Hong Kong A-Level Book 3A92 free rotation about the axis of  bond The molecule has a plane of symmetry  Not asymmetric Q.19Indicate the asymmetric carbon atom(s) in each of the following molecules. Which of them is/are optically active ?

94. New Way Chemistry for Hong Kong A-Level Book 3A93 The optical rotation caused by the left chiral center is cancelled by the optical rotation caused by the right chiral center. Q.19Indicate the asymmetric carbon atom(s) in each of the following molecules. Which of them is/are optically active ? Meso compound internal cancellation

95. New Way Chemistry for Hong Kong A-Level Book 3A94 A meso compound is a compound whose molecules contain 2 or more asymmetric atoms but is optically inactive.

96. New Way Chemistry for Hong Kong A-Level Book 3A95 Two identical groups attached to the carbon  Not asymmetric The same Q.19Indicate the asymmetric carbon atom(s) in each of the following molecules. Which of them is/are optically active ?

97. New Way Chemistry for Hong Kong A-Level Book 3A96 The molecule has a plane of symmetry  Not asymmetric Q.19Indicate the asymmetric carbon atom(s) in each of the following molecules. Which of them is/are optically active ?

98. New Way Chemistry for Hong Kong A-Level Book 3A97 Four different groups attached to the carbon  asymmetric Not the same Q.19Indicate the asymmetric carbon atom(s) in each of the following molecules. Which of them is/are optically active ?

99. New Way Chemistry for Hong Kong A-Level Book 3A98 * * Optically inactive A meso compound Q.19Indicate the asymmetric carbon atom(s) in each of the following molecules. Which of them is/are optically active ?

100. New Way Chemistry for Hong Kong A-Level Book 3A99 Optically inactive A meso compound * * Q.19Indicate the asymmetric carbon atom(s) in each of the following molecules. Which of them is/are optically active ?

101. New Way Chemistry for Hong Kong A-Level Book 3A100 Properties of enantiomers Identical physical properties except their optical activities. (+)butan-2-ol (-)butan-2-ol m.p. 99.5  C 99.5  C

102. New Way Chemistry for Hong Kong A-Level Book 3A101 Properties of enantiomers Identical chemical properties except their reactions with optically active substances.

103. New Way Chemistry for Hong Kong A-Level Book 3A102 Racemic mixture (racemate) An equimolar mixture of a pair of enantiomers Opically inactive The clockwise rotation caused by the (+)isomer is cancelled by the anti-clockwise rotation caused by the (-)isomer external cancellation

104. New Way Chemistry for Hong Kong A-Level Book 3A103 Racemic mixture (racemate) The (+)isomer and (-)isomer are different structures One serves as the impurity of the other in a racemic mixture.  A racemic mixture has a lower m.p. than its components. (+)butan-2-ol (-)butan-2-ol (  )butan-2-ol m.p. 99.5  C 99.5  C <99.5  C

105. New Way Chemistry for Hong Kong A-Level Book 3A104 Identification of solid unknowns 1.By melting point determination Determine the m.p. of the unknown and compare the result with the m.p. of known compounds

106. New Way Chemistry for Hong Kong A-Level Book 3A105 Identification of solid unknowns 2. By mixed melting point determination (more reliable) Mix the unknown solid with a pure solid with known m.p. Determine the m.p. of the mixture and compare the result with the m.p. of the known solid.

107. New Way Chemistry for Hong Kong A-Level Book 3A106 Q.20 Different structures may have the same melting point. In mixed melting point determination, different structures with the same melting point behave as impurities to each other.

108. New Way Chemistry for Hong Kong A-Level Book 3A107 Structure determination of organic compounds from (i) molecular formula (ii) reactions of functional groups (chemical properties) (iii) physical properties (iv)Infra-red / Mass spectra

109. New Way Chemistry for Hong Kong A-Level Book 3A108 C x H y O w N z X(halo)  H Index of unsaturation = 1.Acyclic with single bonds ONLY IOU = 0 CH 4

110. New Way Chemistry for Hong Kong A-Level Book 3A109 CxHyOwNzCxHyOwNz Index of unsaturated = 1.Acyclic with single bonds ONLY IOU = 0 C2H6OC2H6O

111. New Way Chemistry for Hong Kong A-Level Book 3A110 CxHyOwNzCxHyOwNz Index of unsaturated = 1.Acyclic with single bonds ONLY IOU = 0 C 2 H 6 ClN Cl  H + three more

112. New Way Chemistry for Hong Kong A-Level Book 3A111 C 2 H 6 ClN

113. New Way Chemistry for Hong Kong A-Level Book 3A112 2.Acyclic with ONE double bond IOU = 1 C2H4C2H4

114. New Way Chemistry for Hong Kong A-Level Book 3A113 2.Acyclic with ONE double bond IOU = 1 C2H4OC2H4O

115. New Way Chemistry for Hong Kong A-Level Book 3A114 2.Acyclic with ONE double bond IOU = 1 CH 3 O 2 N

116. New Way Chemistry for Hong Kong A-Level Book 3A115 * CH 3 O 2 N E/ZE/Z (+)/(-)

117. New Way Chemistry for Hong Kong A-Level Book 3A116 3.With ONE triple bond IOU = 2 C2H2C2H2

118. New Way Chemistry for Hong Kong A-Level Book 3A117 4.One cyclic IOU = 1 C 6 H 12

119. New Way Chemistry for Hong Kong A-Level Book 3A118 THREE C=C bonds + ONE ring IOU = 4 C6H6C6H6

120. New Way Chemistry for Hong Kong A-Level Book 3A119 Q.21 sp hybridized carbon atoms in triple bond should take a linear shape.

121. New Way Chemistry for Hong Kong A-Level Book 3A120 sp hybridized carbon atoms in triple bond should take a linear shape. Q.21

122. New Way Chemistry for Hong Kong A-Level Book 3A121 312 The carbon atom at the 2nd position, C 2, is sp hybridized  it takes a linear shape. Side-way overlap between p y orbitals of C 1 and C 2 gives a  bond between C 1 and C 2. Side-way overlap between p z orbitals of C 2 and C 3 gives another  bond between C 2 and C 3. Systems with adjacent C=C bonds are less stable than conjugated systems due to a lack of delocalization of  electrons. Q.21

123. New Way Chemistry for Hong Kong A-Level Book 3A122 Q.22(a) C 3 H 6 O Index of unsaturation =  One C=O bond or one C=C bond propanone propanal 7 isomers ! 1 enol 2 enols

124. New Way Chemistry for Hong Kong A-Level Book 3A123 (1E)-prop-1-en-1-ol (1Z)-prop-1-en-1-ol Prop-1-en-2-ol prop-2-en-1-ol methoxyethene C=C + OH C=C + -O- Q.22(a)

125. New Way Chemistry for Hong Kong A-Level Book 3A124 Q.22(b) C 3 H 6 O 2 Index of unsaturation =  One C=O bond or one C=C bond 24 isomers !

126. New Way Chemistry for Hong Kong A-Level Book 3A125 Carboxylic acid or ester propanoic acid methylethanoate ethylmethanoate Q.22(b)

127. New Way Chemistry for Hong Kong A-Level Book 3A126 C=C + two -OH Should have ‘e’ for diol Q.22(b) 1 Prop-2-ene-1,1-diol Prop-1-ene-1,1-diol 1

128. New Way Chemistry for Hong Kong A-Level Book 3A127 C=C + two -OH (1Z)-prop-1-ene-1,2-diol (1E)-prop-1-ene-1,2-diol Q.22(b)

129. New Way Chemistry for Hong Kong A-Level Book 3A128 1 Prop-2-ene-1,2-diol Q.22(b)

130. New Way Chemistry for Hong Kong A-Level Book 3A129 (1Z)-prop-1-ene-1,3-diol (1E)-prop-1-ene-1,3-diol 1 3 1 3 Q.22(b)

131. New Way Chemistry for Hong Kong A-Level Book 3A130 C=C + OH + -O- 1-methoxyethenol (Z)-2-methoxyethenol (E)-2-methoxyethenol 111 Q.22(b)

132. New Way Chemistry for Hong Kong A-Level Book 3A131 (ethenyloxy)methanol ethenyl oxy Q.22(b) C=C + oxy + -OH

133. New Way Chemistry for Hong Kong A-Level Book 3A132 C=O + OH Ketone + alcohol  ketol 1-hydroxypropanone 1 Q.22(b)

134. New Way Chemistry for Hong Kong A-Level Book 3A133 Aldehyde + alcohol  aldol 3-hydroxypropanal 1 * 1 * 1 (+) or (-)2-hydroxypropanal Q.22(b)

135. New Way Chemistry for Hong Kong A-Level Book 3A134 Aldehyde + oxy Q.22(b) 2 2-methoxyethanal

136. New Way Chemistry for Hong Kong A-Level Book 3A135 ene + peroxy Q.22(b) prop-2-en-1-yl hydroperoxide methyl peroxy (methylperoxy)ethene (methylperoxy) Ethenyl methyl peroxide

137. New Way Chemistry for Hong Kong A-Level Book 3A136 ene + peroxy Q.22(b) (1E)-prop-1-en-1-yl hydroperoxide (1Z)-prop-1-en-1-yl hydroperoxide

138. New Way Chemistry for Hong Kong A-Level Book 3A137 prop-1-en-2-yl hydroperoxide Q.22(b)

139. New Way Chemistry for Hong Kong A-Level Book 3A138 C5H8C5H8 Q.22(c) Alkyne : 3 Diene : 8

140. New Way Chemistry for Hong Kong A-Level Book 3A139

141. New Way Chemistry for Hong Kong A-Level Book 3A140 pentadienes

142. New Way Chemistry for Hong Kong A-Level Book 3A141 2-methylbuta-1,3-diene 3-methylbuta-1,2-diene

143. New Way Chemistry for Hong Kong A-Level Book 3A142 Cycloalkene : 10 Bicyclic : 2 Spiro : 1 C5H8C5H8

144. New Way Chemistry for Hong Kong A-Level Book 3A143 * *

145. New Way Chemistry for Hong Kong A-Level Book 3A144 **

146. New Way Chemistry for Hong Kong A-Level Book 3A145 bicyclo[2.1.0]pentane bicyclo[1.1.1]pentane spiro[2.2]pentane