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Introduction to Organic Chemistry · Solutions有机化学入门 · 详解

Companion to the Practice Set · Mark-by-mark walkthroughs · AP-Feeder / ON / BC / AB styles练习题配套答案 · 逐分讲解 · AP 衔接 / 安 / 卑 / 阿省考风格

EASY MEDIUM HARD 🇺🇸 US 🇨🇦 ON 🇨🇦 BC 🇨🇦 AB AP-style MCQAP 风格选择题 AP-feeder FRQAP 衔接简答题 ON Provincial-style安大略省考风格 BC Provincial-style卑诗省考风格 AB Diploma-style阿尔伯塔毕业考风格 Honors荣誉级


PART I  ·  SHORT RESPONSE · SOLUTIONS第一部分  ·  短答题 · 详解AP MCQ + ON/BC/AB short answer · 25 marksAP 选择题 + 安/卑/阿省考短答 · 共 25 分

Section A · Worked SolutionsA 部分 · 详细解答

Q1EASY 🇺🇸 US AP-style MCQAP 风格选择题 §1 Carbon bonding and catenation碳成键与碳链化 · HS-PS1-1 [3 marks][3 分]

Which statement best explains why carbon forms so many organic compounds compared with other elements?以下哪项最能解释碳相比其他元素能形成如此多有机化合物的原因?

Answer:答案:  (B)

(a) Identify the key property that makes carbon unique找出碳的独特性质 M1·A1·A1

Carbon is in Group 14 and has four valence electrons. This allows it to form four covalent bonds simultaneously. Crucially, carbon-carbon bonds are strong enough (bond enthalpy ~347 kJ/mol) to allow carbon to bond to itself repeatedly, forming chains, branches, and rings. This self-bonding ability is called catenation and is the root cause of the enormous diversity of organic molecules. No other element approaches carbon in this ability at ordinary conditions.碳位于第 14 族,具有四个价电子,因此可以同时形成四个共价键。关键在于,碳碳键足够牢固(键焓约 347 kJ/mol),使碳能够反复与自身成键,形成链状、支链及环状结构。这种自我成键能力称为碳链化,是有机分子种类繁多的根本原因。在普通条件下,没有其他元素具有与碳相当的碳链化能力。
Why the distractors fail.干扰项分析。
(A) Carbon is not the most abundant element in the universe; hydrogen and helium are far more abundant. Abundance alone does not explain bonding diversity.碳并非宇宙中含量最多的元素,氢和氦的含量远多于碳。含量多少本身并不能解释成键的多样性。
(C) Carbon forms covalent bonds, not ionic bonds. Organic chemistry is built on covalent bonding.碳形成的是共价键,而非离子键。有机化学建立在共价键的基础上。
(D) Atomic size is not the primary explanation. Silicon is also small and can form four bonds yet has far fewer compounds because Si-Si bonds are weaker and less stable than C-C bonds.原子大小并非主要解释。硅也较小且能形成四个键,但其化合物种类远少于碳,因为 Si-Si 键比 C-C 键弱且不稳定。
Four bonds plus catenation = the foundation of all organic chemistry.四个键加碳链化能力 = 有机化学的全部基础。 The combination of tetravalency (four bonds) and catenation (C-C bonding) lets carbon build an essentially unlimited family of structures: straight chains, branched chains, rings, double bonds, triple bonds, and combinations of all of these. Heteroatoms (N, O, S, halogens) then add further diversity through functional groups. This is why organic chemistry is taught as its own discipline: the structural space is virtually infinite. When answering MCQs about carbon, always look for an option that names both the bonding valence (four bonds) and self-bonding (catenation).四价(四个键)与碳链化(C-C 成键)的结合,使碳能够构建几乎无限多样的结构:直链、支链、环、双键、三键及其各种组合。杂原子(N、O、S、卤素)再通过官能团进一步增加多样性。这就是为什么有机化学被作为独立学科讲授:其结构空间几乎是无穷的。做关于碳的选择题时,务必寻找同时提到成键价数(四个键)和自我成键(碳链化)的选项。
Q2EASY 🇨🇦 ON ON Provincial-style安大略省考风格 §2 Alkane homologous series烷烃同系列 · SCH4U B3.1 [4 marks][4 分]

Answer the following questions about the alkane homologous series.回答以下关于烷烃同系列的问题。

Answer:答案:  (a) $\text{C}_n\text{H}_{2n+2}$  ·  (b) propane $\text{C}_3\text{H}_8$; pentane $\text{C}_5\text{H}_{12}$丙烷 $\text{C}_3\text{H}_8$;戊烷 $\text{C}_5\text{H}_{12}$  ·  (c) boiling point (or melting point / viscosity)沸点(或熔点 / 黏度)

(a) General formula of straight-chain alkanes直链烷烃通式 A1

Each carbon in the chain uses 2 bonds for adjacent carbons and 2 bonds for hydrogen (except the two terminal carbons which have 3 H each). The pattern gives: $\text{C}_n\text{H}_{2n+2}$. Check: methane $n=1$: $\text{CH}_4$ (2(1)+2 = 4 H). Ethane $n=2$: $\text{C}_2\text{H}_6$ (2(2)+2 = 6 H). Correct.链中每个碳用 2 个键连接相邻碳,另外 2 个键连氢(两端碳各有 3 个 H)。规律为:$\text{C}_n\text{H}_{2n+2}$。验证:甲烷 $n=1$:$\text{CH}_4$($2 \times 1 + 2 = 4$ 个 H);乙烷 $n=2$:$\text{C}_2\text{H}_6$($2 \times 2 + 2 = 6$ 个 H)。正确。

(b) Formulas and IUPAC names for $n=3$ and $n=5$$n=3$ 和 $n=5$ 的分子式及 IUPAC 名称 A1·A1

For $n = 3$: $2(3)+2 = 8$ H, so $\text{C}_3\text{H}_8$. IUPAC prefix for 3 carbons is prop-, saturated chain suffix is -ane: propane. For $n = 5$: $2(5)+2 = 12$ H, so $\text{C}_5\text{H}_{12}$. IUPAC prefix for 5 carbons is pent-: pentane.当 $n = 3$ 时:$2(3)+2 = 8$ 个 H,分子式为 $\text{C}_3\text{H}_8$。3 个碳的 IUPAC 前缀为 prop-,饱和链后缀为 -ane丙烷。当 $n = 5$ 时:$2(5)+2 = 12$ 个 H,分子式为 $\text{C}_5\text{H}_{12}$。5 个碳的 IUPAC 前缀为 pent-戊烷

(c) Physical property that increases with chain length随链长增加而升高的物理性质 A1

Boiling point increases as the chain length (and therefore molecular mass) increases. Longer chains have greater surface area, resulting in stronger London dispersion forces between molecules, requiring more energy to separate them into the gas phase. Melting point and viscosity also increase; any of these is acceptable.随着碳链长度(进而分子质量)增大,沸点升高。较长的链具有更大的接触面积,分子间伦敦色散力更强,需要更多能量才能将其分离成气态。熔点和黏度也随之增大;以上任意一个均可接受。
The homologous series: each member differs by $-\text{CH}_2-$ and properties change in a regular trend.同系列:相邻成员相差一个 $-\text{CH}_2-$,物理性质呈规律性变化。 Homologous series members share the same functional group and general formula, differing by a $-\text{CH}_2-$ unit. This explains the smooth trend in boiling points: methane (bp $-162$ degrees C), ethane ($-89$ degrees C), propane ($-42$ degrees C), butane ($-1$ degrees C), pentane (36 degrees C). The first four are gases at room temperature; pentane is a liquid. Knowing the formula and this trend lets you predict properties of unfamiliar members quickly. Do not confuse "boiling point increases" with "stability increases": all simple alkanes are similarly stable toward most reagents.同系列成员具有相同的官能团和通式,相邻成员相差一个 $-\text{CH}_2-$。这解释了沸点的平稳变化趋势:甲烷(沸点 $-162$ 摄氏度)、乙烷($-89$ 摄氏度)、丙烷($-42$ 摄氏度)、丁烷($-1$ 摄氏度)、戊烷(36 摄氏度)。前四种在室温下为气态;戊烷为液态。掌握通式和这一趋势,可以快速预测未知成员的性质。不要将"沸点升高"与"稳定性升高"混淆:所有简单烷烃对大多数试剂的稳定性相似。
Q3MEDIUM 🇨🇦 BC BC Provincial-style卑诗省考风格 §3 Alkenes, alkynes and degree of unsaturation烯烃、炔烃与不饱和度 · BC Chem 11 [6 marks][6 分]

For hydrocarbons with formula $\text{C}_x\text{H}_y$, the degree of unsaturation is $\text{DoU} = \dfrac{2C + 2 - H}{2}$.对于分子式为 $\text{C}_x\text{H}_y$ 的烃,不饱和度为 $\text{DoU} = \dfrac{2C + 2 - H}{2}$。

Answer:答案:  (a) but-1-ene DoU = 1 (one double bond); but-1-yne DoU = 2 (one triple bond)丁-1-烯 DoU = 1(一个双键);丁-1-炔 DoU = 2(一个三键)  ·  (b) benzene, DoU = 4 consistent with 3 double bonds + 1 ring苯,DoU = 4 与 3 个双键 + 1 个环吻合

(a) Calculate DoU for but-1-ene and but-1-yne计算丁-1-烯和丁-1-炔的不饱和度 M1·A1·M1·A1

But-1-ene, $\text{C}_4\text{H}_8$: $C = 4$, $H = 8$.丁-1-烯,$\text{C}_4\text{H}_8$:$C = 4$,$H = 8$。 $$ \text{DoU} \;=\; \frac{2(4) + 2 - 8}{2} \;=\; \frac{10 - 8}{2} \;=\; \frac{2}{2} \;=\; 1. $$ DoU = 1 indicates one degree of unsaturation: here one carbon-carbon double bond ($\text{C=C}$). The molecule is monounsaturated.DoU = 1 表示一个不饱和度:即一个碳碳双键($\text{C=C}$)。该分子为单不饱和化合物。
But-1-yne, $\text{C}_4\text{H}_6$: $C = 4$, $H = 6$.丁-1-炔,$\text{C}_4\text{H}_6$:$C = 4$,$H = 6$。 $$ \text{DoU} \;=\; \frac{2(4) + 2 - 6}{2} \;=\; \frac{10 - 6}{2} \;=\; \frac{4}{2} \;=\; 2. $$ DoU = 2 indicates two degrees of unsaturation: here one carbon-carbon triple bond ($\text{C}\equiv\text{C}$), which counts as two degrees (one sigma + one additional pi bond beyond the double bond).DoU = 2 表示两个不饱和度:即一个碳碳三键($\text{C}\equiv\text{C}$),它计为两个不饱和度(一个 sigma 键 + 一个超出双键的额外 pi 键)。

(b) Name benzene and explain DoU = 4命名苯并解释 DoU = 4 A1·A1

The compound $\text{C}_6\text{H}_6$ is benzene. Its accepted structure is a regular hexagonal ring with three alternating double bonds (the Kekule representation) or equivalently a delocalized aromatic ring. DoU = 4 accounts for: 1 ring (closes a ring: +1) plus 3 double bonds (each +1) = 4 total. Verify: $\frac{2(6)+2-6}{2} = \frac{8}{2} = 4$. The DoU of 4 is consistent because the ring closure itself counts as one degree.$\text{C}_6\text{H}_6$ 即。其公认结构为正六边形环,含三个交替双键(Kekule 式),等价地也可表示为离域芳香环。DoU = 4 的来源:1 个环(成环:+1)加上 3 个双键(各 +1)= 共 4 个。验证:$\frac{2(6)+2-6}{2} = \frac{8}{2} = 4$。DoU = 4 与此结构吻合,因为成环本身也计为一个不饱和度。
Each ring or pi bond contributes exactly 1 to the DoU; a triple bond contributes 2.每个环或 pi 键各贡献 1 个不饱和度;三键贡献 2 个。 The DoU formula $\frac{2C+2-H}{2}$ tells you the total count of rings plus pi bonds. DoU 0 = saturated (alkane or cycloalkane with 0 rings not counted separately by this formula: be careful, the ring version IS included). A useful check: every degree of unsaturation reduces the H count by 2 compared to the saturated parent. DoU is additive: a molecule with one ring and two double bonds has DoU = 3. For heteroatoms: each N adds 1 to the count ($+\frac{1}{2}$ per N in the numerator convention); each O or S does not change DoU; each halogen acts like H (subtracts 1 from H count effectively). At high school level, you only need the C/H version of the formula.公式 $\frac{2C+2-H}{2}$ 给出环与 pi 键数目之和。DoU = 0 表示饱和(此公式中烷烃 DoU = 0,环烷烃的环计入其中)。实用检验:每增加一个不饱和度,H 数比饱和母体减少 2。DoU 具有加和性:含 1 个环和 2 个双键的分子 DoU = 3。含杂原子时:每个 N 使计数增加 1(分子中 N 的贡献为 $+\frac{1}{2}$);每个 O 或 S 不改变 DoU;每个卤素相当于一个 H(从 H 数中减 1)。高中阶段只需掌握 C/H 版本的公式。
Q4MEDIUM 🇨🇦 AB AB Diploma-style阿尔伯塔毕业考风格 §4 IUPAC naming of branched alkanes and alkenes支链烷烃与烯烃的 IUPAC 命名 · Chem 30 GO1 [6 marks][6 分]

Apply IUPAC naming rules to each of the following.将 IUPAC 命名规则应用于以下各题。

Answer:答案:  (a) 2-methylpentane  ·  (b) 3-methylbut-1-ene  ·  (c) $\text{CH}_3\text{CH}(\text{CH}_3)\text{CH}(\text{CH}_3)\text{CH}_3$

(a) IUPAC name for $\text{CH}_3\text{CH}(\text{CH}_3)\text{CH}_2\text{CH}_2\text{CH}_3$$\text{CH}_3\text{CH}(\text{CH}_3)\text{CH}_2\text{CH}_2\text{CH}_3$ 的 IUPAC 名称 M1·A1

Count the longest continuous chain: C1-C2-C3-C4-C5 (5 carbons, pentane parent). The $-\text{CH}_3$ branch is on C2 of the chain. Number from the end closest to the branch: branch on C2 vs C4 if numbered from the other end, so C2 gives lower locant. Name: 2-methylpentane.找最长连续碳链:C1-C2-C3-C4-C5(5 个碳,母体为戊烷)。$-\text{CH}_3$ 支链连在链的 C2 上。从距支链最近的一端编号:从该端编号支链在 C2,从另一端编号则在 C4,故取 C2(较小定位数)。名称:2-甲基戊烷

(b) IUPAC name for $\text{CH}_3\text{CH}(\text{CH}_3)\text{CH}{=}\text{CH}_2$$\text{CH}_3\text{CH}(\text{CH}_3)\text{CH}{=}\text{CH}_2$ 的 IUPAC 名称 M1·A1

The longest chain containing the double bond: $\text{CH}_2{=}\text{CH}-\text{CH}(\text{CH}_3)-\text{CH}_3$ (reading from the double-bond end). That is 4 carbons with a double bond at C1: but-1-ene parent. The $-\text{CH}_3$ branch is on C3 (numbering so the double bond has the lower locant). Name: 3-methylbut-1-ene.找含双键的最长链:从双键端读为 $\text{CH}_2{=}\text{CH}-\text{CH}(\text{CH}_3)-\text{CH}_3$,共 4 个碳,双键在 C1:母体为丁-1-烯。$-\text{CH}_3$ 支链在 C3(编号使双键定位数最小)。名称:3-甲基丁-1-烯

(c) Condensed structural formula for 2,3-dimethylbutane2,3-二甲基丁烷的简式 M1·A1

Parent chain: butane (4 C). Methyl groups at C2 and C3. Each interior carbon of the parent already bonds to two chain carbons, so each has one remaining bond for the methyl and one for H:母体链:丁烷(4 个 C)。甲基分别在 C2 和 C3 上。母体链的两个内部碳各已与两个链碳成键,因此各有一个键接甲基,一个键接 H: $$ \text{CH}_3\text{-CH(CH}_3\text{)-CH(CH}_3\text{)-CH}_3 $$ Written as condensed formula: $\text{CH}_3\text{CH}(\text{CH}_3)\text{CH}(\text{CH}_3)\text{CH}_3$.简式写法:$\text{CH}_3\text{CH}(\text{CH}_3)\text{CH}(\text{CH}_3)\text{CH}_3$。
IUPAC naming three-step algorithm: (1) find longest chain, (2) give functional group / branch lowest locant, (3) name substituents alphabetically.IUPAC 命名三步法:(1) 找最长碳链,(2) 使官能团/支链定位数最小,(3) 按字母顺序命名取代基。 The most common error is not choosing the longest chain correctly. For branched structures, draw out the chain explicitly and count every possible path before deciding. For alkenes and alkynes, the chain must include the multiple bond, and the multiple bond gets the lower locant even if that means a branch gets a higher number. In (b), if you numbered from the methyl end, the double bond would be at C3, giving "2-methylbut-3-ene" which is wrong because the double bond must be given priority in numbering.最常见错误是未能正确找出最长碳链。对于支链结构,务必明确画出链并数清每条可能路径后再作判断。对于烯烃和炔烃,最长链必须包含多键,多键优先取较小定位数,即使这会使支链定位数变大。在 (b) 中,若从甲基端编号,双键将在 C3,得到"2-甲基丁-3-烯",这是错误的,因为双键在编号时必须优先取最小值。
Q5MEDIUM 🇺🇸 US AP-style MCQAP 风格选择题 §5 Functional groups官能团 · HS-PS1-1 · SCH4U B2.1 [6 marks][6 分]

For each compound, identify (i) the functional-group class and (ii) the functional group present.对于每种化合物,写出 (i) 官能团类别和 (ii) 所含官能团。

Answer:答案:  (a) alcohol; $-\text{OH}$ (hydroxyl)醇;$-\text{OH}$(羟基)  ·  (b) carboxylic acid; $-\text{COOH}$ (carboxyl)羧酸;$-\text{COOH}$(羧基)  ·  (c) ketone; $\text{C=O}$ (carbonyl flanked by two carbons)酮;$\text{C=O}$(两侧均为碳的羰基)

(a) $\text{CH}_3\text{CH}_2\text{OH}$$\text{CH}_3\text{CH}_2\text{OH}$ A1·A1

The $-\text{OH}$ (hydroxyl) group is bonded to a carbon that is not a carbonyl carbon. This defines an alcohol. The compound is ethanol. Functional group: hydroxyl $-\text{OH}$.$-\text{OH}$(羟基)连接在非羰基碳上,这定义了类。该化合物为乙醇。官能团:羟基 $-\text{OH}$

(b) $\text{CH}_3\text{COOH}$$\text{CH}_3\text{COOH}$ A1·A1

The $-\text{COOH}$ (carboxyl) group contains both a carbonyl ($\text{C=O}$) and a hydroxyl ($-\text{OH}$) on the same carbon. This defines a carboxylic acid. The compound is ethanoic acid (acetic acid). Functional group: carboxyl $-\text{COOH}$.$-\text{COOH}$(羧基)在同一碳上同时含有羰基($\text{C=O}$)和羟基($-\text{OH}$),这定义了羧酸类。该化合物为乙酸(乙酸)。官能团:羧基 $-\text{COOH}$

(c) $\text{CH}_3\text{COCH}_3$$\text{CH}_3\text{COCH}_3$ A1·A1

The $\text{C=O}$ (carbonyl) group is between two carbon chains (not at a chain end). This is the defining feature of a ketone. The compound is propan-2-one (acetone). If the carbonyl were at a chain end attached to one H, it would be an aldehyde. Functional group: carbonyl $\text{C=O}$ (internal).$\text{C=O}$(羰基)位于两段碳链之间(不在链端),这是类的定义特征。该化合物为丙-2-酮(丙酮)。若羰基在链端并与一个 H 相连,则为醛。官能团:羰基 $\text{C=O}$(内部)。
The position of $\text{C=O}$ distinguishes aldehyde from ketone; the full $-\text{COOH}$ distinguishes carboxylic acid from both.$\text{C=O}$ 的位置区分醛与酮;完整的 $-\text{COOH}$ 将羧酸与两者区分开来。 Functional group identification is a pattern-matching skill. Key diagnostics: $-\text{OH}$ on non-carbonyl C = alcohol; $-\text{COOH}$ (carbonyl + OH on same C, at chain end) = carboxylic acid; $-\text{CHO}$ (carbonyl + H, at chain end) = aldehyde; internal $\text{C=O}$ (no H on carbonyl C, flanked by two C) = ketone; $-\text{NH}_2$ = amine; $-\text{COO}-$ (ester linkage) = ester. Memorizing the condensed structural formula for each is more reliable than memorizing names alone, because names can be confused but the drawn formula makes the structural distinction obvious.官能团的识别是一种模式匹配技能。关键判断依据:$-\text{OH}$ 在非羰基碳上 = 醇;$-\text{COOH}$(同一碳上同时有羰基和 OH,位于链端)= 羧酸;$-\text{CHO}$(羰基 + H,位于链端)= 醛;内部 $\text{C=O}$(羰基碳无 H,两侧均为 C)= 酮;$-\text{NH}_2$ = 胺;$-\text{COO}-$(酯键)= 酯。记住每类的简式比单纯记名称更可靠,因为名称容易混淆,而结构式使结构区别一目了然。
PART II  ·  EXTENDED RESPONSE · SOLUTIONS第二部分  ·  简答题 · 详解AP-feeder FRQ + honors · 30 marksAP 衔接简答题 + 荣誉级 · 共 30 分

Section B · Worked SolutionsB 部分 · 详细解答

Q6MEDIUM 🇺🇸 US AP-feeder FRQAP 衔接简答题 §4 IUPAC naming: branched alkanes and alkynesIUPAC 命名:支链烷烃与炔烃 · HS-PS1-1 [8 marks][8 分]

Apply IUPAC rules step by step.逐步应用 IUPAC 规则。

Answer:答案:  (a) 3-methylpentane  ·  (b) $\text{CH}_3\text{C}{\equiv}\text{CCH}(\text{CH}_3)\text{CH}_2\text{CH}_3$  ·  (c) lowest locant rule applied to branches对支链应用最低定位数规则

(a) Name $\text{CH}_3\text{CH}_2\text{CH}(\text{CH}_3)\text{CH}_2\text{CH}_3$命名 $\text{CH}_3\text{CH}_2\text{CH}(\text{CH}_3)\text{CH}_2\text{CH}_3$ M1·A1

Step 1 - longest chain: reading the condensed formula left to right, the main backbone is $\text{CH}_3\text{CH}_2 - \text{CH} - \text{CH}_2\text{CH}_3$ = 5 carbons (pentane). The $-\text{CH}_3$ hanging off the central C is a branch. Step 2 - number the chain so the branch has the lowest locant: from left end, branch is on C3; from right end, also C3. So the branch is at C3. Step 3: name = 3-methylpentane.第 1 步 - 最长链:从左至右读简式,主链为 $\text{CH}_3\text{CH}_2 - \text{CH} - \text{CH}_2\text{CH}_3$ = 5 个碳(戊烷)。悬挂在中央碳上的 $-\text{CH}_3$ 为支链。第 2 步 - 编号使支链定位数最小:从左端编号,支链在 C3;从右端编号,也在 C3。故支链位于 C3。第 3 步:名称 = 3-甲基戊烷

(b) Draw 4-methylhex-2-yne and label the triple bond画出 4-甲基己-2-炔并标注三键 M1·A1·A1

Parent: hex-2-yne = 6-carbon chain with triple bond starting at C2. Methyl branch at C4. Build from C1: $\text{CH}_3$ (C1) $-$ triple bond $-$ C3$\text{H}$ $-$ C4$\text{H}(\text{CH}_3)$ $-$ C5$\text{H}_2$ $-$ C6$\text{H}_3$.母体:己-2-炔 = 6 碳链,三键从 C2 开始。甲基支链在 C4。从 C1 构建:$\text{CH}_3$(C1)$-$ 三键 $-$ C3$\text{H}$ $-$ C4$\text{H}(\text{CH}_3)$ $-$ C5$\text{H}_2$ $-$ C6$\text{H}_3$。 $$ \text{CH}_3 \underbrace{-\text{C}{\equiv}\text{C}-}_{\text{triple bond}} \text{CH}(\text{CH}_3)\text{CH}_2\text{CH}_3 $$ Condensed: $\text{CH}_3\text{C}{\equiv}\text{CCH}(\text{CH}_3)\text{CH}_2\text{CH}_3$.简式:$\text{CH}_3\text{C}{\equiv}\text{CCH}(\text{CH}_3)\text{CH}_2\text{CH}_3$。

(c) Why 2,2-dimethylbutane not 3,3-dimethylbutane为何命名为 2,2-二甲基丁烷而非 3,3-二甲基丁烷 M1·A1·A1

The compound $\text{CH}_3\text{C}(\text{CH}_3)_2\text{CH}_2\text{CH}_3$ has a 4-carbon longest chain (butane parent). The quaternary carbon bearing two methyls is adjacent to C1. Numbering from the end closest to the substituted carbon: the two methyls are at C2, giving the locant set {2,2}. If numbered from the other end, the set would be {3,3}. The IUPAC rule applied is the lowest set of locants rule: when comparing two possible numbering schemes, choose the one that gives the lower locant at the first point of difference. {2,2} vs {3,3}: 2 < 3 at the first comparison, so {2,2} wins. Name: 2,2-dimethylbutane.化合物 $\text{CH}_3\text{C}(\text{CH}_3)_2\text{CH}_2\text{CH}_3$ 的最长链为 4 个碳(母体丁烷)。带两个甲基的季碳紧邻 C1。从距取代碳最近的一端编号:两个甲基均在 C2,定位数组为 {2,2}。若从另一端编号,定位数组为 {3,3}。所用 IUPAC 规则为最低定位数组规则:比较两种可能的编号方式时,在首个不同处取较小定位数的方案优先。{2,2} vs {3,3}:首次比较 2 < 3,故 {2,2} 胜出。名称:2,2-二甲基丁烷
Always number the chain to give the lowest possible locants to substituents, not just the lowest number to one substituent.编号时应使取代基的定位数组整体最小,而非仅使某一取代基的定位数最小。 The "lowest set of locants" rule compares the full locant sets as ordered sequences. It is not simply "sum of locants is smallest" (though for simple cases this gives the same answer). For 2,2-dimethylbutane vs 3,3-dimethylbutane: sums are 4 vs 6, consistent. But if you had locant sets {1,3} vs {2,4}, compare first elements: 1 < 2, so {1,3} wins even though the sum (4) equals the sum of the other (6 is actually larger here). For alkynes and alkenes, the multiple bond position takes precedence over branch position in the numbering decision."最低定位数组"规则将完整定位数组作为有序序列进行比较,而不仅仅是"定位数之和最小"(尽管对简单情况两者结果相同)。对于 2,2-二甲基丁烷 vs 3,3-二甲基丁烷:两者定位数之和分别为 4 和 6,结论一致。但若定位数组为 {1,3} vs {2,4},比较第一个元素:1 < 2,故 {1,3} 胜出,尽管和(4)小于另一组的和(6,此处确实更大)。对于炔烃和烯烃,多键位置在编号决策中优先于支链位置。
Q7MEDIUM 🇨🇦 ON ON Provincial-style安大略省考风格 §6 Structural isomers of butane and pentane丁烷与戊烷的结构同分异构体 · SCH4U B2.2 [7 marks][7 分]

Structural isomers share the same molecular formula but differ in the arrangement of atoms.结构同分异构体具有相同的分子式,但原子排列方式不同。

Answer:答案:  (a) butane + 2-methylpropane丁烷 + 2-甲基丙烷  ·  (b) 3 isomers; pentane has highest boiling point3 种同分异构体;戊烷沸点最高

(a) Two structural isomers of $\text{C}_4\text{H}_{10}$$\text{C}_4\text{H}_{10}$ 的两种结构同分异构体 M1·A1·M1·A1

Isomer 1 (straight chain): $\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_3$, IUPAC name: butane.同分异构体 1(直链): $\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_3$,IUPAC 名称:丁烷
Isomer 2 (branched): $\text{CH}_3\text{CH}(\text{CH}_3)\text{CH}_3$, which is a 3-carbon chain with a methyl branch on C2. IUPAC name: 2-methylpropane (also called isobutane).同分异构体 2(支链): $\text{CH}_3\text{CH}(\text{CH}_3)\text{CH}_3$,即 3 碳链在 C2 上有一个甲基支链。IUPAC 名称:2-甲基丙烷(又称异丁烷)。
Verify both have formula $\text{C}_4\text{H}_{10}$: isomer 1: 4 C, $2(4)+2=10$ H. Isomer 2: 3 C parent + 1 C branch = 4 C total; same 10 H. These are the only two; a 3-membered ring $\text{C}_3$ cannot accommodate a 4th C and give $\text{C}_4\text{H}_{10}$ without changing the formula.验证两者均为 $\text{C}_4\text{H}_{10}$:同分异构体 1:4 个 C,$2(4)+2=10$ 个 H。同分异构体 2:3 个 C 母链 + 1 个 C 支链 = 共 4 个 C;同样 10 个 H。这是仅有的两种;3 元环 $\text{C}_3$ 无法再容纳第 4 个 C 而保持 $\text{C}_4\text{H}_{10}$ 的分子式。

(b) Isomers of $\text{C}_5\text{H}_{12}$ and highest boiling point$\text{C}_5\text{H}_{12}$ 的同分异构体及最高沸点 A1·M1·A1

There are three structural isomers of $\text{C}_5\text{H}_{12}$: (1) pentane $\text{CH}_3(\text{CH}_2)_3\text{CH}_3$; (2) 2-methylbutane $\text{CH}_3\text{CH}(\text{CH}_3)\text{CH}_2\text{CH}_3$; (3) 2,2-dimethylpropane $\text{C}(\text{CH}_3)_4$.$\text{C}_5\text{H}_{12}$ 共有三种结构同分异构体:(1) 戊烷 $\text{CH}_3(\text{CH}_2)_3\text{CH}_3$;(2) 2-甲基丁烷 $\text{CH}_3\text{CH}(\text{CH}_3)\text{CH}_2\text{CH}_3$;(3) 2,2-二甲基丙烷 $\text{C}(\text{CH}_3)_4$。
The isomer with the highest boiling point is pentane (bp 36 degrees C). The straight chain has the greatest molecular surface area, allowing the most contact between molecules and therefore the strongest London dispersion forces. More energy is needed to overcome these forces in the liquid phase, resulting in a higher boiling point. (2-Methylbutane bp 28 degrees C; 2,2-dimethylpropane bp 9.5 degrees C.)沸点最高的同分异构体为戊烷(沸点 36 摄氏度)。直链结构分子表面积最大,分子间接触最多,因此伦敦色散力最强。克服液相中这些力所需的能量最大,沸点最高。(2-甲基丁烷沸点 28 摄氏度;2,2-二甲基丙烷沸点 9.5 摄氏度。)
Branching reduces boiling point by decreasing molecular surface area and therefore weakening London dispersion forces.支链化通过减小分子表面积进而削弱伦敦色散力,使沸点降低。 London dispersion forces (also called van der Waals forces or induced dipole-induced dipole forces) arise from temporary fluctuations in electron density. They are proportional to the surface area available for molecular contact. A linear chain like pentane presents more surface area than a compact spherical molecule like 2,2-dimethylpropane (neopentane). This is a key AP/IB concept: all else being equal, branching lowers the boiling point compared to the straight-chain isomer of the same molecular formula. The molecular mass is the same for all three isomers, so mass cannot explain the boiling point differences.伦敦色散力(也称范德瓦耳斯力或诱导偶极-诱导偶极力)源于电子密度的瞬时涨落,与可供分子接触的表面积成正比。线状链(如戊烷)比球形紧凑分子(如 2,2-二甲基丙烷,即新戊烷)具有更大的表面积。这是 AP/IB 的核心考点:在其他条件相同的情况下,与相同分子式的直链异构体相比,支链化使沸点降低。三种同分异构体的分子质量相同,因此质量无法解释沸点差异。
Q8HARD 🇨🇦 BC BC Provincial-style卑诗省考风格 §7 Organic reactions: combustion, addition, substitution有机反应:燃烧、加成、取代 · BC Chem 12 · SCH4U B3.3 [8 marks][8 分]

Write balanced chemical equations and classify each reaction type.写出配平的化学方程式并判断各反应类型。

Answer:答案:  (a) combustion燃烧  ·  (b) addition; 1,2-dibromoethane加成;1,2-二溴乙烷  ·  (c) free-radical substitution自由基取代

(a) Complete combustion of propane丙烷的完全燃烧 M1·A1

For complete combustion of a hydrocarbon: all C becomes $\text{CO}_2$, all H becomes $\text{H}_2\text{O}$. Propane $\text{C}_3\text{H}_8$:烃完全燃烧时:所有 C 生成 $\text{CO}_2$,所有 H 生成 $\text{H}_2\text{O}$。丙烷 $\text{C}_3\text{H}_8$: $$ \text{C}_3\text{H}_8 \;+\; 5\,\text{O}_2 \;\longrightarrow\; 3\,\text{CO}_2 \;+\; 4\,\text{H}_2\text{O} $$ Balance check: C: 3=3, H: 8=8, O: 10=10. Reaction type: combustion.配平检验:C:3=3,H:8=8,O:10=10。反应类型:燃烧

(b) Addition of bromine to ethene溴与乙烯的加成反应 M1·A1·M1·A1

$$ \text{CH}_2{=}\text{CH}_2 \;+\; \text{Br}_2 \;\longrightarrow\; \text{CH}_2\text{Br-CH}_2\text{Br} $$ The product is 1,2-dibromoethane (also called 1,2-dibromoethane or ethylene dibromide). Reaction type: addition.产物为 1,2-二溴乙烷(也称二溴乙烷)。反应类型:加成
Alkenes (but not alkanes) undergo addition reactions because the C=C double bond has a pi bond that is weaker and more accessible than the sigma bond. The pi bond electrons act as a nucleophilic site, attracting electrophiles (here, $\text{Br}_2$). Alkanes have only strong sigma bonds and are largely unreactive toward electrophilic addition; they react by free-radical substitution instead, requiring UV light or high temperature.烯烃(而非烷烃)发生加成反应,因为 C=C 双键中含有比 sigma 键更弱且更易接近的 pi 键。pi 键电子作为亲核位点,能吸引亲电试剂(此处为 $\text{Br}_2$)。烷烃只有强 sigma 键,对亲电加成基本不反应;它们通过自由基取代反应与卤素反应,需要紫外光或高温。

(c) Free-radical substitution of methane with chlorine甲烷与氯气的自由基取代反应 M1·A1

$$ \text{CH}_4 \;+\; \text{Cl}_2 \;\xrightarrow{\text{h}\nu}\; \text{CH}_3\text{Cl} \;+\; \text{HCl} $$ Reaction type: free-radical substitution (halogenation of an alkane). The $\text{h}\nu$ (or sunlight / UV) symbol above the arrow indicates photoinitiation. One H on methane is replaced by one Cl; the other Cl bonds with the displaced H to form HCl.反应类型:自由基取代(烷烃卤化反应)。箭头上方的 $\text{h}\nu$(或"光照")符号表示光引发。甲烷上一个 H 被一个 Cl 取代;另一个 Cl 与脱离的 H 结合生成 HCl。
The three classic organic reaction types at high school: combustion, addition, and substitution. Each has a diagnostic condition and tells you about the reactant type.高中三种经典有机反应类型:燃烧、加成和取代。每种均有诊断性条件,并揭示反应物类型。 Combustion: excess $\text{O}_2$, produces $\text{CO}_2 + \text{H}_2\text{O}$ (complete) or $\text{CO} + \text{H}_2\text{O}$ (incomplete). Addition: requires a pi bond in the reactant (alkene or alkyne), no small-molecule by-product. Substitution: replaces one atom with another; for alkanes + halogens it is free-radical (UV required); for alcohols + acids it is condensation. Knowing which type applies to which functional group / class is the exam skill being tested across Q8 and Q9.燃烧:需过量 $\text{O}_2$,产物为 $\text{CO}_2 + \text{H}_2\text{O}$(完全燃烧)或 $\text{CO} + \text{H}_2\text{O}$(不完全燃烧)。加成:反应物中需含 pi 键(烯烃或炔烃),无小分子副产物。取代:用一个原子替换另一个;烷烃与卤素的反应为自由基取代(需紫外光);醇与酸的反应为缩合。掌握各类反应类型适用于哪类官能团/化合物类别,是 Q8 和 Q9 所考查的核心技能。
Q9HARDHonors荣誉级 🇺🇸 US AP-feeder FRQAP 衔接简答题 §5 + §7 Functional groups + esterification官能团 + 酯化反应 · SCH4U B3.3 (above standard floor)(超出标准范围) [7 marks][7 分]

Ethanol ($\text{CH}_3\text{CH}_2\text{OH}$) reacts with ethanoic acid ($\text{CH}_3\text{COOH}$) in a condensation reaction in the presence of a concentrated sulfuric acid catalyst.乙醇($\text{CH}_3\text{CH}_2\text{OH}$)与乙酸($\text{CH}_3\text{COOH}$)在浓硫酸催化下发生缩合反应。

Answer:答案:  (a) ethanol: alcohol / $-\text{OH}$; ethanoic acid: carboxylic acid / $-\text{COOH}$乙醇:醇 / $-\text{OH}$;乙酸:羧酸 / $-\text{COOH}$  ·  (b) ethyl ethanoate + water乙酸乙酯 + 水  ·  (c) ester linkage $-\text{COO}-$; condensation = small molecule (water) released酯键 $-\text{COO}-$;缩合 = 释放小分子(水)

(a) Functional groups of the reactants反应物的官能团 A1·A1

Ethanol $\text{CH}_3\text{CH}_2\text{OH}$: contains the hydroxyl group $-\text{OH}$ attached to a non-carbonyl carbon. Functional-group class: alcohol.乙醇 $\text{CH}_3\text{CH}_2\text{OH}$:含羟基 $-\text{OH}$,连接在非羰基碳上。官能团类别:
Ethanoic acid $\text{CH}_3\text{COOH}$: contains the carboxyl group $-\text{COOH}$ (a carbonyl and a hydroxyl on the same carbon). Functional-group class: carboxylic acid.乙酸 $\text{CH}_3\text{COOH}$:含羧基 $-\text{COOH}$(同一碳上同时含羰基和羟基)。官能团类别:羧酸

(b) Balanced esterification equation and product names配平的酯化方程式及产物名称 M1·A1·A1

$$ \text{CH}_3\text{COOH} \;+\; \text{CH}_3\text{CH}_2\text{OH} \;\underset{\Delta}{\overset{\text{conc. H}_2\text{SO}_4}{\rightleftharpoons}}\; \text{CH}_3\text{COOCH}_2\text{CH}_3 \;+\; \text{H}_2\text{O} $$ Products: ethyl ethanoate (the ester, $\text{CH}_3\text{COOCH}_2\text{CH}_3$) and water. The reaction is reversible (equilibrium arrows are acceptable). The sulfuric acid acts as a catalyst and is not consumed.产物:乙酸乙酯(酯类,$\text{CH}_3\text{COOCH}_2\text{CH}_3$)和。该反应可逆(使用可逆箭头可接受)。浓硫酸作为催化剂,不被消耗。

(c) New functional group and classification as condensation新官能团及缩合反应分类 A1·A1

The new functional group formed in the ester product is the ester linkage $-\text{COO}-$ (also written $-\text{C}(=\text{O})\text{O}-$). This links the carbonyl carbon of the acid fragment to the oxygen from the alcohol fragment.酯类产物中新形成的官能团为酯键 $-\text{COO}-$(也写作 $-\text{C}(=\text{O})\text{O}-$),将酸片段的羰基碳与醇片段的氧原子相连。
This reaction is a condensation reaction because two molecules join together with the simultaneous elimination of a small molecule (here water). The $-\text{OH}$ from the carboxylic acid and the $-\text{H}$ from the alcohol hydroxyl combine to form $\text{H}_2\text{O}$, and the remaining fragments bond through the ester linkage.此反应为缩合反应,因为两个分子结合的同时脱去一个小分子(此处为水)。羧酸的 $-\text{OH}$ 与醇羟基的 $-\text{H}$ 结合生成 $\text{H}_2\text{O}$,剩余片段通过酯键相连。
Esterification: acid + alcohol yields ester + water. The ester name follows the pattern: alkyl (from alcohol) + acid name with -ic replaced by -ate.酯化反应:酸 + 醇生成酯 + 水。酯的命名规律:醇来源的烷基 + 酸名(将 -ic 替换为 -ate)。 Ethanol gives "ethyl"; ethanoic acid gives "ethanoate": so the ester is ethyl ethanoate. This naming pattern generalises: methanol + propanoic acid gives methyl propanoate. The equilibrium nature of esterification is important at the AP level: concentrated $\text{H}_2\text{SO}_4$ acts as a dehydrating agent (removing water to shift equilibrium right) in addition to being a catalyst. At provincial level, stating that the reaction is reversible and that excess of one reactant or removal of a product drives it forward is sufficient. Esterification is an example of a condensation reaction; hydrolysis (the reverse) is an example of an elimination or addition reaction depending on conditions.乙醇对应"乙基(ethyl)";乙酸对应"乙酸酯(ethanoate)":故酯类产物为乙酸乙酯。此命名规律可推广:甲醇 + 丙酸生成丙酸甲酯。酯化反应的可逆性在 AP 层面尤为重要:浓 $\text{H}_2\text{SO}_4$ 除作催化剂外,还作为脱水剂(通过去除水将平衡向右移动)。在省考层面,说明反应可逆、某一反应物过量或除去产物可使反应正向进行即可。酯化反应是缩合反应的典型例子;其逆反应(水解)则属于消除或加成反应,具体取决于条件。
PART III  ·  MODELING / APPLIED · SOLUTIONS第三部分  ·  建模与应用 · 详解AB Diploma + Universal · 25 marks阿省毕业考 + 通用题型 · 共 25 分

Section C · Worked SolutionsC 部分 · 详细解答

Q10MEDIUM 🇨🇦 AB AB Diploma-style阿尔伯塔毕业考风格 §6 All structural isomers of $\text{C}_5\text{H}_{12}$$\text{C}_5\text{H}_{12}$ 的所有结构同分异构体 · Chem 30 GO1 [8 marks][8 分]

Structural isomers have the same molecular formula but different connectivity of atoms.结构同分异构体具有相同的分子式,但原子连接方式不同。

Answer:答案:  (a) pentane; 2-methylbutane; 2,2-dimethylpropane戊烷;2-甲基丁烷;2,2-二甲基丙烷  ·  (b) 2,2-dimethylpropane has the lowest boiling point2,2-二甲基丙烷沸点最低

(a) All three structural isomers of $\text{C}_5\text{H}_{12}$$\text{C}_5\text{H}_{12}$ 的全部三种结构同分异构体 M1·A1·M1·A1·M1·A1

Isomer 1 - pentane (straight 5-carbon chain):同分异构体 1 - 戊烷(5 碳直链): $$ \text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_3 $$ All five carbons in a row; no branches. IUPAC name: pentane. Boiling point 36 degrees C.五个碳全部成一排,无支链。IUPAC 名称:戊烷。沸点 36 摄氏度。

Isomer 2 - 2-methylbutane (one methyl branch on C2 of a 4-carbon chain):同分异构体 2 - 2-甲基丁烷(4 碳链 C2 上有一个甲基支链): $$ \text{CH}_3\text{CH}(\text{CH}_3)\text{CH}_2\text{CH}_3 $$ Longest chain: 4 C (butane parent). One methyl branch at C2. IUPAC name: 2-methylbutane. Boiling point 28 degrees C.最长链:4 个 C(母体丁烷)。C2 上有一个甲基支链。IUPAC 名称:2-甲基丁烷。沸点 28 摄氏度。

Isomer 3 - 2,2-dimethylpropane (two methyl branches on C2 of a 3-carbon chain, also called neopentane):同分异构体 3 - 2,2-二甲基丙烷(3 碳链 C2 上有两个甲基支链,又称新戊烷): $$ \text{C}(\text{CH}_3)_4 $$ Central carbon bonded to four methyl groups. Longest chain: 3 C (propane parent). Two methyls at C2. IUPAC name: 2,2-dimethylpropane. Boiling point 9.5 degrees C.中心碳与四个甲基相连。最长链:3 个 C(母体丙烷)。C2 上有两个甲基。IUPAC 名称:2,2-二甲基丙烷。沸点 9.5 摄氏度。

(b) Isomer with lowest boiling point沸点最低的同分异构体 A1·A1

2,2-Dimethylpropane (neopentane, bp 9.5 degrees C) has the lowest boiling point. Its near-spherical shape minimises the molecular surface area available for intermolecular contact. Smaller surface area means weaker London dispersion forces between molecules. Therefore less thermal energy is needed to overcome these forces and transition to the gas phase, resulting in the lowest boiling point of the three isomers.2,2-二甲基丙烷(新戊烷,沸点 9.5 摄氏度)沸点最低。其近球形外形使分子间接触的表面积最小,伦敦色散力最弱。因此克服这些力并转变为气态所需的热能最少,沸点在三种异构体中最低。
Systematic approach for drawing all isomers: reduce the main chain length one by one, placing branches at each possible carbon.系统画出所有同分异构体的方法:逐步缩短主链,在每个可能的碳上添加支链。 For $\text{C}_5\text{H}_{12}$: start with the maximum chain (5 C, no branches = pentane). Then try 4-C parent: one methyl branch can only go on C2 (C3 would give the same structure by symmetry, just numbered from the other end). Then try 3-C parent: two methyls must both go on C2 (putting them on C1 is impossible as that would extend the chain; C3 is the same as C2 by symmetry). No further reduction is possible (a 2-C parent would need 3 methyls = too many bonds on one carbon). This gives exactly three distinct structures: pentane, 2-methylbutane, 2,2-dimethylpropane. This systematic method is reliable for exam questions and avoids duplicates.对于 $\text{C}_5\text{H}_{12}$:从最长链开始(5 个 C,无支链 = 戊烷)。然后尝试 4 碳母体:一个甲基支链只能放在 C2(放在 C3 由于对称性与放在 C2 是同一种结构,只是从另一端编号)。再尝试 3 碳母体:两个甲基必须都放在 C2(放在 C1 上不可能,因为那会延长主链;C3 与 C2 对称等价)。无法进一步缩短(2 碳母体需要 3 个甲基,某碳键数超出)。这恰好给出三种不同结构:戊烷、2-甲基丁烷、2,2-二甲基丙烷。这种系统方法在考试中可靠且避免重复。
Q11MEDIUM 🇺🇸 US AP-feeder FRQAP 衔接简答题 §4 + §5 IUPAC naming with functional groups含官能团的 IUPAC 命名 · SCH4U B2.1 · B2.2 [9 marks][9 分]

For each compound: (i) give the IUPAC name, (ii) identify the functional-group class, and (iii) name the functional group present.对于每种化合物:(i) 写出 IUPAC 名称,(ii) 指出官能团类别,(iii) 命名所含官能团。

Answer:答案:  (a) butanal / aldehyde / $-\text{CHO}$  ·  (b) pentan-3-one / ketone / carbonyl $\text{C=O}$  ·  (c) butan-2-ol / alcohol / $-\text{OH}$

(a) $\text{CH}_3\text{CH}_2\text{CH}_2\text{CHO}$$\text{CH}_3\text{CH}_2\text{CH}_2\text{CHO}$ A1·A1·A1

(i) IUPAC name: The $-\text{CHO}$ group is at the end of the chain and defines the carbon it is on as C1. Total chain: 4 C (including the CHO carbon). Parent: butane with the suffix $-al$ for aldehyde. Name: butanal.(i) IUPAC 名称:$-\text{CHO}$ 在链端,其所在碳定义为 C1。总链:4 个 C(含 CHO 碳)。母体:丁烷,醛的后缀为 $-al$。名称:丁醛(butanal)。
(ii) Functional-group class: aldehyde.(ii) 官能团类别:
(iii) Functional group: aldehyde group $-\text{CHO}$ (carbonyl carbon with one H, at the chain terminus).(iii) 官能团:醛基 $-\text{CHO}$(链端含一个 H 的羰基碳)。

(b) $\text{CH}_3\text{CH}_2\text{COCH}_2\text{CH}_3$$\text{CH}_3\text{CH}_2\text{COCH}_2\text{CH}_3$ A1·A1·A1

(i) IUPAC name: 5-carbon chain with $\text{C=O}$ in the middle. The $\text{C=O}$ is on C3 (numbering from either end gives C3 for the carbonyl; verify: from left C3 gives locant 3; from right also C3; the compound is symmetric). Parent: pentane, suffix $-one$ with locant. Name: pentan-3-one.(i) IUPAC 名称:5 碳链,$\text{C=O}$ 在中间。$\text{C=O}$ 位于 C3(从任一端编号均为 C3;验证:从左端 C3,从右端也是 C3;该化合物对称)。母体:戊烷,酮的后缀为 $-one$ 加定位数。名称:戊-3-酮(pentan-3-one)。
(ii) Functional-group class: ketone.(ii) 官能团类别:
(iii) Functional group: carbonyl group $\text{C=O}$ (internal, flanked by two carbon-containing groups).(iii) 官能团:羰基 $\text{C=O}$(内部,两侧均为含碳基团)。

(c) $\text{CH}_3\text{CH}(\text{OH})\text{CH}_2\text{CH}_3$$\text{CH}_3\text{CH}(\text{OH})\text{CH}_2\text{CH}_3$ A1·A1·A1

(i) IUPAC name: 4-carbon chain with $-\text{OH}$ on C2. Number from the end closest to $-\text{OH}$: $-\text{OH}$ at C2 (from the left end) vs C3 (from the right end). Lower locant is C2. Parent: butane with suffix $-ol$. Name: butan-2-ol.(i) IUPAC 名称:4 碳链,$-\text{OH}$ 在 C2 上。从距 $-\text{OH}$ 最近的一端编号:从左端 $-\text{OH}$ 在 C2,从右端在 C3。较小定位数为 C2。母体:丁烷,醇的后缀为 $-ol$。名称:丁-2-醇(butan-2-ol)。
(ii) Functional-group class: alcohol.(ii) 官能团类别:
(iii) Functional group: hydroxyl group $-\text{OH}$.(iii) 官能团:羟基 $-\text{OH}$
Naming compounds with functional groups: the suffix changes with the functional group and the locant is placed immediately before it in modern IUPAC nomenclature.含官能团化合物的命名:后缀随官能团变化,定位数在现代 IUPAC 命名中紧置于其前。 Suffixes: alkane $-\text{ane}$; alkene $-\text{ene}$; alkyne $-\text{yne}$; alcohol $-\text{ol}$; aldehyde $-\text{al}$ (C1 implied, no locant needed); ketone $-\text{one}$; carboxylic acid $-\text{oic acid}$ (C1 implied). Modern IUPAC places the locant immediately before the suffix: butan-2-ol, pentan-3-one. Older conventions place the locant after the parent name: 2-butanol. Both may appear in Canadian curriculum materials; know both. The aldehyde carbon is always C1 by definition, so butanal needs no locant. Likewise, the carboxyl carbon is always C1 in carboxylic acids.后缀:烷烃 $-\text{ane}$;烯烃 $-\text{ene}$;炔烃 $-\text{yne}$;醇 $-\text{ol}$;醛 $-\text{al}$(C1 隐含,无需定位数);酮 $-\text{one}$;羧酸 $-\text{oic acid}$(C1 隐含)。现代 IUPAC 将定位数紧置于后缀前:butan-2-ol、pentan-3-one。旧惯例将定位数置于母体名称后:2-butanol。两种写法均可能出现在加拿大课程教材中,需两者都掌握。醛碳按定义始终为 C1,故丁醛无需定位数;同样,羧酸中羧基碳始终为 C1。
Q12HARD 🇺🇸 US AP-feeder FRQAP 衔接简答题 §7 Polymers: addition and condensation polymerization聚合物:加聚反应与缩聚反应 · SCH4U B3.3 · HS-PS2-6 [8 marks][8 分]

Polymers are large molecules formed by joining many monomer units through repeated reactions.聚合物是由许多单体单元通过反复反应连接而成的大分子。

Answer:答案:  (a) $[-\text{CH}_2-\text{CH}(\text{CH}_3)-]_n$; C=C broken, C-C formed$[-\text{CH}_2-\text{CH}(\text{CH}_3)-]_n$;C=C 断裂,C-C 形成  ·  (b) ester linkage; $\text{H}_2\text{O}$ released酯键;释放 $\text{H}_2\text{O}$  ·  (c) addition needs C=C, no by-product; condensation needs bifunctional monomers, releases small molecule加聚需要 C=C,无副产物;缩聚需要双官能团单体,释放小分子

(a) Addition polymerization of propene to polypropylene丙烯加聚反应生成聚丙烯 M1·A1·A1

In addition polymerization, the $\text{C=C}$ double bond of each propene monomer opens and the monomers link into a chain. The repeating unit is the open-chain version of propene:加聚反应中,每个丙烯单体的 $\text{C=C}$ 双键打开,单体连接成链。重复单元为丙烯的开链形式: $$ n\,\text{CH}_2{=}\text{CHCH}_3 \;\longrightarrow\; [-\text{CH}_2-\text{CH}(\text{CH}_3)-]_n $$ The repeating unit enclosed in brackets with subscript $n$ is $[-\text{CH}_2-\text{CH}(\text{CH}_3)-]_n$. Bond broken during polymerization: the pi bond of the $\text{C=C}$ double bond (a C=C double bond becomes two C-C single bonds as monomers link). Bond formed: a new C-C sigma bond between adjacent monomer units.括号内加下标 $n$ 的重复单元为 $[-\text{CH}_2-\text{CH}(\text{CH}_3)-]_n$。聚合过程中断裂的键:$\text{C=C}$ 双键中的 pi 键(C=C 双键变为两个 C-C 单键,使单体相互连接)。形成的键:相邻单体单元之间新的 C-C sigma 键

(b) Condensation polymerization of diol and diacid to polyester二醇与二酸缩聚反应生成聚酯 M1·A1·A1

One condensation step between a diol and a diacid:二醇与二酸之间一步缩合反应: $$ \text{HO-R-OH} \;+\; \text{HOOC-R'-COOH} \;\longrightarrow\; \text{HO-R-OOC-R'-COOH} \;+\; \text{H}_2\text{O} $$ Small molecule released: water ($\text{H}_2\text{O}$). The linkage formed between the two monomers is the ester linkage ($-\text{COO}-$). Each condensation step releases one molecule of water and extends the polymer chain by one monomer unit. The polymer is called a polyester.释放的小分子:水($\text{H}_2\text{O}$)。两个单体之间形成的键为酯键($-\text{COO}-$)。每一步缩合释放一个水分子,并使聚合物链延长一个单体单元。所得聚合物称为聚酯

(c) Key difference: addition vs condensation polymerization关键区别:加聚反应与缩聚反应 A1·A1

(i) Type of monomer: addition polymerization requires monomers containing a C=C double bond (or other pi bond); condensation polymerization requires monomers with two functional groups (bifunctional) such as a diol and a diacid.(i) 单体类型:加聚反应需要含 C=C 双键(或其他 pi 键)的单体;缩聚反应需要含两个官能团(双官能团)的单体,如二醇和二酸。
(ii) By-product: addition polymerization releases no small-molecule by-product (all atoms in the monomers are incorporated into the polymer); condensation polymerization releases a small molecule by-product (commonly water, but also HCl in some nylon syntheses).(ii) 副产物:加聚反应不释放小分子副产物(单体中的所有原子均并入聚合物);缩聚反应释放小分子副产物(通常为水,但某些尼龙合成中也会释放 HCl)。
Addition polymers retain all atoms of the monomer; condensation polymers lose a small molecule at each step, making the polymer chain grow more slowly and requiring exact stoichiometry.加聚物保留单体的全部原子;缩聚物每步丢失一个小分子,使聚合物链增长较慢,且需要精确的化学计量比。 This distinction has practical consequences: addition polymers (polyethylene, polypropylene, PVC) are typically formed by free-radical chain reactions that are very fast; the molecular mass climbs quickly. Condensation polymers (polyesters like PET, polyamides like nylon) require each step to proceed and are generally slower; removing the water by-product (e.g., in a vacuum or with a dehydrating agent) is essential to drive the reaction to high molecular mass. At the AP level, you should be able to identify a polymer as addition or condensation from the repeating unit: if the repeating unit contains the same atoms as the monomer in a simple ratio, it is addition; if the repeating unit is missing atoms compared to the monomer sum, it is condensation.这一区别具有实际意义:加聚物(聚乙烯、聚丙烯、PVC)通常通过自由基链式反应形成,速度很快,分子量迅速升高。缩聚物(聚酯如 PET、聚酰胺如尼龙)需要每步反应都进行,速度相对较慢;去除副产物水(如在真空中或使用脱水剂)对于获得高分子量聚合物至关重要。在 AP 层面,应能从重复单元判断聚合物类型:若重复单元原子与单体简单比例相同,则为加聚物;若重复单元原子比单体总和少,则为缩聚物。