HKDSE Chemistry – Chemistry of Carbon Compounds

HKDSE Chemistry Core
Section 11: Chemistry of Carbon Compounds | 碳化合物的化學

Billy Sir’s Smart Notes: Master Organic Reactions, Physical Properties, Synthesis, and Polymers.
由資深導師 Billy Sir 編寫,助你極速掌握有機反應、物理性質、合成路徑及聚合物。

1. Basics of Organic Chemistry | 有機化學基礎

Organic chemistry is the study of carbon-containing compounds. 有機化學是研究含碳化合物的科學。

  • Homologous Series (同系物): A family of organic compounds with the same general formula, similar chemical properties, and a gradual change in physical properties. Each member differs by a \( \text{-CH}_2\text{-} \) unit. 具有相同通式、相似化學性質及物理性質呈漸變規律的一系列有機化合物。相鄰成員相差一個 \( \text{-CH}_2\text{-} \) 單位。
  • Functional Group (官能基): An atom or a group of atoms that determines the chemical properties of an organic compound (e.g., \( \text{-OH} \) for alcohols, \( \text{-COOH} \) for carboxylic acids). 決定有機化合物化學性質的原子或原子團(例如醇的 \( \text{-OH} \),羧酸的 \( \text{-COOH} \))。
  • IUPAC Naming (系統命名法): Identify the longest carbon chain (prefix: meth-, eth-, prop-, but-, etc.), number from the end closest to the functional group/substituent, and add the appropriate suffix (-ane, -ene, -ol, -oic acid). 找出最長碳鏈,從最靠近官能基/取代基的一端開始編號,並加上適當的字尾。

2. Physical Properties | 物理性質

🌡️ Melting/Boiling Points & Density | 熔點/沸點與密度

  • 1. Hydrogen Bonding (氫鍵): Alcohols, carboxylic acids, and amides have much higher m.p. and b.p. than alkanes/alkenes of similar mass due to the presence of strong intermolecular hydrogen bonds. 醇、羧酸和酰胺由於存在強大的分子間氫鍵,其熔點和沸點遠高於質量相若的烷烴/烯烴。
  • 2. Polar Molecules (極性分子): Compounds with polar functional groups (e.g., aldehydes, ketones, haloalkanes) experience dipole-dipole interactions, giving them higher m.p./b.p. than non-polar hydrocarbons of similar size, but lower than those with hydrogen bonds. 帶有極性官能基的化合物(如醛、酮、鹵代烷)具有偶極-偶極引力,其熔點/沸點高於體積相若的非極性烴類,但低於具有氫鍵的分子。
  • 3. Molecular Size (分子體積): For molecules in the same homologous series, as the carbon chain gets longer, the molecular size increases, leading to stronger van der Waals’ forces (dispersion forces) between molecules. Thus, m.p., b.p., and density increase. 對於同一同系物,碳鏈越長,分子體積越大,分子間的范德華力(色散力)越強。因此熔點、沸點和密度上升。
  • 4. Shape (分子形狀): For isomers, a straight chain provides a larger surface area for intermolecular contact, strengthening van der Waals’ forces and favoring a higher boiling point (b.p.). On the other hand, a highly branched chain makes the molecule more spherical and symmetrical, allowing it to pack more closely in a solid crystal lattice, which favors a higher melting point (m.p.) and density. 對於異構體,直鏈提供較大的分子間接觸表面積,增強范德華力,有利於較高的沸點(b.p.)。另一方面,高度支鏈使分子更接近球體且對稱,使其在固體晶格中能更緊密地堆積,從而有利於較高的熔點(m.p.)和密度

💧 Solubility in Water | 水溶性

“Like dissolves like” (相似相溶):

  • Hydrocarbons (Alkanes, Alkenes) and Haloalkanes are insoluble in water (hydrophobic). 烴類和鹵代烷不溶於水(疏水性)。
  • Lower alcohols, aldehydes, ketones, and carboxylic acids (1-3 carbons) are soluble in water because their hydrophilic functional groups can form hydrogen bonds with water. 低級醇、醛、酮和羧酸可溶於水,因為其親水官能基能與水形成氫鍵。
  • As the carbon chain lengthens, the hydrophobic effect dominates, and solubility in water decreases. 隨著碳鏈變長,疏水效應佔優,水溶性下降。

3. Summary of Organic Reactions | 有機反應總結

Mastering these reactions is crucial for DSE. Memorize the reagents and conditions! 掌握這些反應對 DSE 考試至關重要。請熟記試劑和條件!

Reactant (反應物) Reaction & Reagents (反應及試劑) Product (生成物) Remarks (備註)
Alkane / Alkene \( + \text{O}_2 \) (Combustion) \( \text{CO}_2 + \text{H}_2\text{O} + \text{CO} + \text{C} \dots \) Complete gives \( \text{CO}_2 \); Incomplete gives \( \text{CO} \) or \( \text{C} \).
完全燃燒產生二氧化碳;不完全燃燒產生一氧化碳或碳。
Longer Alkane Heat + Catalyst (Cracking) Shorter Alkane + Alkene Breaks large molecules into useful smaller ones.
裂解作用:將大分子斷裂成有用的小分子。
Alkane \( + \text{X}_2 \) (UV light or heat) Haloalkane + \( \text{HX} \) Free radical substitution. (\( \text{X = Cl, Br} \))
自由基取代反應。
Alkene \( + \text{X}_2 \) (in organic solvent) Dihaloalkane Addition reaction. (\( \text{X = Cl, Br, I} \))
加成反應。
\( + \text{H}_2 \) (Pt, Ni or Pd catalyst) Alkane Hydrogenation (Addition).
加氫反應。
\( + \text{HX} \) (room temp.) Haloalkane Prediction of major product by Markovnikov’s Rule is required! (\( \text{X = F, Cl, Br, I} \))
需用馬可尼科夫法則預測主產物!
Cold & dilute alkaline \( \text{KMnO}_4(aq) \)
or Cold & dilute \( \text{KMnO}_4/\text{H}^+(aq) \)
Diol (二醇) Oxidation. Purple \( \text{MnO}_4^- \) decolorizes.
氧化反應。紫色高錳酸根褪色。
Haloalkane \( + \text{OH}^-(aq) \) (Heat under reflux) Alcohol Nucleophilic substitution.
親核取代反應。
Alcohol \( + \text{HX} \) or \( \text{PX}_3 \) Haloalkane Substitution. (\( \text{X = Cl, Br, I} \))
取代反應。
\( \text{Al}_2\text{O}_3 \) (heat) or conc. \( \text{H}_2\text{SO}_4 \) (heat) Alkene + \( \text{H}_2\text{O} \) Dehydration (Elimination).
脫水反應(消除反應)。
1° Alcohol
(伯醇)
\( \text{Cr}_2\text{O}_7^{2-}/\text{H}^+(aq) \) (Heat + Distillation) Aldehyde (醛) Distill immediately to prevent further oxidation.
立即蒸餾以防止進一步氧化。
\( \text{MnO}_4^-/\text{H}^+(aq) \) or \( \text{Cr}_2\text{O}_7^{2-}/\text{H}^+(aq) \) (Heat under reflux) Carboxylic acid (羧酸) Complete oxidation. Reflux ensures full reaction.
完全氧化。回流確保反應完全。
2° Alcohol
(仲醇)
\( \text{MnO}_4^-/\text{H}^+(aq) \) or \( \text{Cr}_2\text{O}_7^{2-}/\text{H}^+(aq) \) (Heat under reflux) Ketone (酮) Ketones cannot be easily oxidized further.
酮難以被進一步氧化。
Carboxylic acid or Aldehyde 1. \( \text{LiAlH}_4 \), dry ether
2. \( \text{H}^+(aq) \)
1° Alcohol For Aldehyde or Ketone, \( \text{NaBH}_4(aq) \) can also be used as the RA (Reducing Agent).
對於醛或酮,也可使用 \( \text{NaBH}_4(aq) \) 作為還原劑。
Ketone 1. \( \text{LiAlH}_4 \), dry ether
2. \( \text{H}^+(aq) \)
2° Alcohol
Carboxylic acid + Alcohol conc. \( \text{H}_2\text{SO}_4 \), heat Ester + Water Reversible reaction (Esterification).
可逆反應(酯化作用)。
Ester \( \text{H}^+(aq) \), heat Carboxylic acid + Alcohol Acidic hydrolysis (Reversible).
酸性水解(可逆)。
Ester 1. \( \text{OH}^-(aq) \), heat Carboxylate (ion) + Alcohol Alkaline hydrolysis (Irreversible), followed by acidification.
鹼性水解(不可逆),隨後加入酸以回收羧酸。
2. \( \text{H}^+(aq) \) (added to Carboxylate ion) Carboxylic acid
Carboxylic acid 1. \( \text{PCl}_3 \), 2. \( \text{NH}_3 \)
or \( \text{NH}_3 \), heat
Unsubstituted amide Formation of amide.
酰胺的生成。

⚠️ Exam Trap: Markovnikov’s Rule | 考試陷阱:馬可尼科夫法則

When adding \( \text{HX} \) or \( \text{H}_2\text{O} \) to an unsymmetrical alkene, the Hydrogen atom attaches to the carbon of the double bond that already has more hydrogen atoms. This forms the more stable carbocation intermediate, leading to the major product. 當 \( \text{HX} \) 加成到不對稱烯烴時,氫原子會連接到原本已帶有較多氫原子的雙鍵碳上。這會形成較穩定的碳陽離子中間體,從而產生主產物。

4. Common Organic Synthesis | 常見有機合成路徑

In DSE, you are often asked to design a multi-step synthesis. Connect the reactions you memorized! 在 DSE 中,常要求設計多步合成。將你背熟的反應連接起來!

Example: Ethene \( \rightarrow \) Ethanoic Acid

\( \text{CH}_2\text{=CH}_2 \xrightarrow{\text{HCl}} \text{CH}_3\text{CH}_2\text{Cl} \xrightarrow[\text{reflux}]{\text{NaOH(aq)}} \text{CH}_3\text{CH}_2\text{OH} \xrightarrow[\text{reflux}]{\text{Cr}_2\text{O}_7^{2-}/\text{H}^+} \text{CH}_3\text{COOH} \)

Alkene \( \rightarrow \) Haloalkane \( \rightarrow \) Primary Alcohol \( \rightarrow \) Carboxylic Acid

5. Important Organic Products | 重要有機產品

🧼 1. Soap and Detergents | 肥皂與清潔劑

  • Saponification (皂化反應): Fat/Oil + \( \text{NaOH(aq)} \xrightarrow{\text{heat}} \) Soap (Sodium salt of fatty acid) + Glycerol (丙三醇).
  • Cleaning Action: Soap has a hydrophilic ionic head (dissolves in water) and a hydrophobic hydrocarbon tail (dissolves in oil/grease). It acts as an emulsifier, breaking oil into tiny droplets (micelles) suspended in water. 肥皂具有親水性離子頭(溶於水)和疏水性碳氫尾(溶於油污)。它作為乳化劑,將油污分解成懸浮在水中的微小液滴。

💊 2. Aspirin | 阿士匹靈

  • Aspirin is an analgesic (painkiller). It is synthesized via Esterification (酯化反應).
  • Reactants: Salicylic acid (水楊酸) + Ethanoic anhydride (乙酸酐) or Ethanoyl chloride.
  • Note: Ethanoic acid can be used with conc. \( \text{H}_2\text{SO}_4 \), but ethanoic anhydride is preferred as it gives a higher yield and doesn’t produce water (which could reverse the reaction). 乙酸酐是更佳選擇,因為產率較高且不產生水。

🔗 3. Polymers | 聚合物

Type (類型) Addition Polymerization (加成聚合) Condensation Polymerization (縮合聚合)
Monomer Feature
單體特徵
Contains \( \text{C=C} \) double bond.
含有碳碳雙鍵。
Contains two functional groups (e.g., diol, dicarboxylic acid, diamine).
含有兩個官能基。
By-product
副產物
None. 100% atom economy.
無。
Small molecules eliminated (e.g., \( \text{H}_2\text{O}, \text{HCl} \)).
釋出小分子(如水)。
Examples
例子
Poly(ethene) [PE], Poly(propene) [PP], PVC, Polystyrene. Polyesters (e.g., PET), Polyamides (e.g., Nylon), Kevlar.

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