We learnt in Grade 11 that substances have different physical properties because of the TYPE and STRENGTH of the intermolecular forces that are present in that substance. Organic compounds are excellent examples of this. we ow MELTING POINT VADoup POLSSuprLondon forces - between non-polar molecules dipole-dipole forces - forces between polar molecules Hydrogen bonds - unusually strong ofpole-cfpole forces between polar molecules which conan a nydragen atom bonded to a NOF atom (The molecule is a strong dipole Ott because of this) 1S These ave in your definition sheet but wont be asked as definitions. Just important to remember.BOILING POINT the temperature at which the vapour pressure of a liquid equals the external atmospheric pressure above the liquid a VAPOUR PRESSURE eo) the pressure exerted by a vapour in equilibrium with its liquid in a closed container. Os MELTING POINT Temperature at which the solid and liquid phases are in equilibrium. Learn this on€ (The temperature at which a solid changes state to a liquid) (USefulto remembers Solubiity _: LIKE DISSOLVES LIKE)FACTORS THAT AFFECT THE STRENGTH OF INTERMOLECULAR FORCES (IMF) The table below (from the Grade 11 textbook) shows us the three factors that affect the strength of intermolecular forces. We were introduced to this last year. i Description Different types of intermolecular forces have different Typeolatracion TREND 3 | creraths: london forces < dipole-dipole forces < hydrogen bonding ; TREND 7 London forces are stronger between larger Relative molecular mass of molecule molecules with bigger molar masses London forces between long thin molecules are greater than Shape of molecule TREND 2. those between short round molecues because they can lie closer together. This year, the above three factors will be explored in relation to organic compounds. We will see how each of the factors affects their physical properties.London forces are stronger a 5 BN D il between larger molecules with bigger molecular masses We see this trend exhibited within each of the homologous series (families) that we have studied: The LONGER THE CARBOM CHAIN, the more carbon atoms in the molecule, the LARGER Tile MOLECULAR MASS and therefore the STRONGER THE LONDON FORCES between the molecules. More energy is therefore needed to overcome the stronger London forces and this in turn WCREASES VE NELVING AND BOMMNNE POWT and PECREASES THE VAPOUR PRESSURE. os S&S methane ethane propane butane4, To explore this factor properly, a FAIR TEST WD needs to be conducted. This means that other © - factors that can affect the IMF strength must be controlled and kept the same. independant variable: (changed on purpose): length of the carbon chain / molecular mass dependant variable: (measured during experiment): melting point or boiling point or vapour pressure. controlled variables: (remains the same): * same homologous series / same functional group * same number of branchesTREMD ie ‘compounds below: © are all alkanes (same homologous series / functional group) © are all Straight chained. independant variable dependant variable 1 Methane Cari, CH 16 2 Ethane cay C2He 30 3 Propane C3 44 ABT yy] -25 843 3 4 Butane CaHio 58 138, a 05 2 | 8 5 Pentane — CsHiz 72 130 DB} 36 §68 | 5 liquid 6 Hexane Cotta 86 25 2] 69 17,6 | — liguid 7 Heptane Cri 100 a1] 8 53 liquid 8 Octane Cotg 114 58 126 4,47 liquid 9 Nonane —CoHyp 128 “5 151 1,33 liquid 40 Decane Cota 142 30 174 0.17 liquid 48 Octadecane CisHse 254 28 316 oo solid 419 Nonadecane Ci Hyo 268 2 329 = solid“-hexanol | 1564 _|TREND f: CARBOXYLIC AGS ants (L. formica) vinegar (L. acetum) valericacid valerianroot _| pentanoicacid | _-34.52C == enanthic acid | vines (Gk. oenanthe) | heptanoic acid 15% |_capryicacid | goats(tcaper) | ectancicacid | 16.38 | pelargonic acid | pelargonium (anherb)| nonanoic acid capric acid goats (L. caper)i: HALOALKAIES Haloalkanes will show the same trend as the other homologous series as the carbon chain gets longer. HOWEVER: the molecular mass can also be increased by changing the type of halogen atom in the functional group. aa CH3CHoF = CHsCH2Cl_—CHsCHaBr = CHaCHal_——_chai length. BP: -38°C BP: 12°C BP: 39°C BPE 72°C ig ave all straight chained. Compounds: © are all haloalkanes © have the SAME carbon The MP and BP of haloalkanes increase as size of X increases (X = F,Cl, Bror |). This is due to the molecular mass increasing and therefore the strength of the London forces.STANDARD TEMPLATE TO USE WHEN ANSWERING TREND 4 EXPLANATION TYPE QUESTIONS: © As the number of carbon atoms in the chain increases, the molecular mass increases. ¢ The London forces therefore increase in strength ¢ More energy is needed to break the London forces * Melting point / boiling point therefore increase / vapour pressure decreases.TREND 1 QUESTIONS 1. The boiling points of different organic compounds are given below: BOILING POINT (°C HCOOH CHyCOOH CHsCH,COOH — CH3CH,CH,COOH 1.1 Define boiling point (2) 1.2 Write down the: 1.2.1 name of the FUNCTIONAL GROUP of these compounds (1) 1.2.2 IUPAC name of compound C. (1) 1.2.3 structural formula of the FUNCTIONAL isomer of compound B. (2) 1.3 Fully explain the difference between the boiling points by referring to the type and strength of the intermolecular forces in these compounds.(3) 1.4 Which ONE of the compounds A or B or C has the highest vapour pressure? Refer to the data in the table to give a reason for your answer. (2). An experiment is conducted to determine the boiling points of the organic compounds shown below. Organic compound Relative Boiling Point Molecular Mass (ec) P CHsF -78,3 Q CHsCt -24,1 R CHsBr 37 2.1 Define the term homologous series. (2) 2.2 Formulate an investigative question for the experiment. (2) 2.3 Name the homologous series the above compounds belong to. (1) 2.4 From the table, write down the IUPAC names of TWO compounds that will be gaseous at -20 °C. (2) 2.5 Name a variable that was kept constant in this experiment. (1) 2.6 Describe the trend in the boiling points of the compounds. 2.7 Explain the trend in QUESTION 2.6 above. Make reference to INTERMOLECULAR FORCES and ENERGY needed in your explanation. (3)3. The table below shows the vapour pressures of various organic compounds at 25 °C. ‘Compound Molar mass Vapour Pressure (g-mor") (x10? Pay pentane 72 573.0 hexane 86 160.0 propan-t-ol 60 propan-2-ol 60 butan-1-o1 74 6.2 butan-2-01 74 18,3 3.1 Write down the IUPAC name and structural formula of an isomer of pentane. (2) 3.2 Name the homologous series that hexane and pentane belong to. (1) 3.3 Give the structural formula of the functional group of propan-2-ol 3.4 Explain the difference in vapour pressure between pentane and hexane. Refer to the strength of intermolecular forces in your answer. (3) 3.5 Would the vapour pressure of propan-1-ol be HIGHER, LOWER or the SAME as the vapour pressure of butan-1-ol?4, The vapour pressure versus temperature graph below was obtained for four straight chain (unbranched) alkanes (P, Q, R and S). From P to S, EACH COMPOUND DIFFERS FROM THE PREVIOUS. COMPOUND BY A -CH2 GROUP. The vapour pressures are measured in mm Hg. Atmospheric pressure is 760 mm Hg (Graph of vapour prese.ure versus tempersture a Vapour pressure (mmHg) ‘Temperature (°C) 4.1 Give a reason why alkanes are said to be SATURATED. (1) 4.2 Use the information in the graph above to answer the following: 4.2.1 What is the effect of an increase in temperature on vapour pressure? INCREASES, DECREASES or NO EFFECT. (1)4.2.2 Which compound has a boiling point of approximately 68 °C? Give a reason for your answer. (2) 4.2.3, Which compound has the longest chain length? Fully explain the answer. (4) 4.3 Compound P has FIVE carbon atoms. 4.3.1 Draw the structural formula of a chain isomer of P. Write down the IUPAC name of this isomer. (3) 4.3.2 How will the vapour pressure of this isomer compare with that of compound P? HIGHER THAN, LOWER THAN or EQUAL TO. (1)London forces between long thin molecules kk FA 2 are greater than those between short round molecues because they can lie closer together. We see this trend exhibited within each of the homologous series (families) that we have studied: STRAIGHT CHAI molecules have SVRONGER LONDON FORCES between them since they can be closer to each other. ERAWCKED CHAINS form more spherical molecules and have WEAKER LOMPON FORCES between them. More energy is therefore needed to overcome the stronger London forces in straight chains and this in turn INCREASES ThE (MELTING ANDD COILING POINT and PECREASES THE VAPOUR PRESSURE, Cin Se DD me i Gt cH Se ei) Larger contact arees Z| More spherical with tower Sn oP awh auonger a poins er contect with weak SE ay |) torsos or arvacton / ee ceeeamaiee oh OsTo explore this factor properly, a FAIR TEST needs to be conducted. This means that other factors that can affect the IMF strength must be controlled and kept the same. independant variable: (changed on purpose): number of branches in the chain (shape of molecule) dependant variable: (measured during experiment): (melting point or) boiling point or vapour pressure. controlled variables: (remains the same): * same homologous series / same functional group thus TYPE of intermolecular force will be the same. © same number of carbon atoms / same molecular mass &.g compare chain LsomersH HOH aa L || a CsHia " a 2,2-dimethylpropane " molecular mass = 72 gol“! boiling point = 9 °C 7kPa| 21°C) number of branches increases aa SEEDS SST SO NSPE eT vapour pressure increasesSTANDARD TEMPLATE TO USE WHEN ANSWERING TREND 2 EXPLANATION TYPE QUESTIONS: * As the number of branches in the molecule increases, it becomes more spherical / its surface area decreases. © The London forces therefore decrease in strength * Less. energy is needed to break the London forces * (Melting point) / boiling point therefore decrease / vapour pressure increases.TREND 2 QUESTIONS 1. The condensed structural formulas, melting and boiling points of three molecules with the molecular formula C7Hy¢ are given below. Condensed Compour ‘structure formula heptane CHgCH CH2CH2CH CH3CH3 2-methylhexane CH3CH(CH3)CH2CH2CH3CH3 2,2,3+trimethylbutane (CH3)s;CCH(CH3)2 PON'T WORRY NEVER SEEN ASKED 1.1 Why are these compounds structural isomers? What type of isomers are they? 1.2 Draw the structural formula of 2,2,3-trimethylbutane 1.3 Predict which of 2-methylhexane and 2,2,3-trimethylbutane has the highest vapour pressure. Explain your answer by referring to MOLECULAR STRUCTURE, INTERMOLECULAR FORCES and the ENERGY NEEDED.Consider the three structural isomers of the compound with molecular formula C4H;90. Name the homologous series these compounds belong to. Classify each of A, B and C as primary, secondary or tertiary. Give the IUPAC name of compound B and C. Which compound A or C has the lowest boiling point? Give a reason for your answer by referring to the strength of the intermolecuar forces present in each. Which of A, B or C has the lowest vapour pressure at the same temperature? Give a reason for your answer by referring to the molecular structure of the compounds.3. Three hydrocarbons (A, B and C) with molecular formula CsH12 are used to investigate the effect of BRANCHES on the VAPOUR PRESSURE of hydrocarbons. The results obtained are shown in the table below. Hydrocarbons | Vapor pressure (mmHg) A 450 B 592 c 1102 3.1 Define the term ‘hydrocarbon’ 3.2 Write down the term used to describe compounds with the same molecular formula but different structural formula. 3.3. Identify the: 3.3.1 independant variable 3.3.2 dependant variable 3.3.3 controlled variable(s) 3.4 Are these hydrocarbons saturated or unsaturated? Explain.3.5 One of the hydrocarbons (A, B or C) has a straight chain with no branches. Write down the following: 3.5.1 the letter (A, B or C) that represents this hydrocarbon. 3.5.2 its IUPAC name 3.6 Consider hydrocarbon C and its vapour pressure.. 3.6.1 Write down the structural formula of C. 3.6.2 Explain why C has the highest vapour pressure. In your answer refer to MOLECULAR STRUCTURE, INTERMOLECULAR FORCES and the ENERGY needed. 3.7 Which of A, B or C has the highest boiling point? 4. Compounds € and D have the same number of branches, but their boiling points differ considerably. Give a reason for this. CHa CH3 1 c CHs=CH-CH-SHs D CHs—C—CHy—CHs CH BP = 58 °C BP = 50°CDifferent types of intermolecular Ts 5 EAN 5) 3 forces have different strengths: london < dipole-dipole < hydrogen bonding We see this trend exhibited when we compare organic compounds with different functional groups (different homologous series). The TYPE AND STRENGTH of the intermolecular forces ina compound is determined by its FUNCTIONAL GROUP, The more polar the functional group, the more polar the molecule and the stronger the IMFs. The STRONGER ThE IMF (H-bonds > dipole- dipole > London forces), the more energy is needed to overcome them and this in turn INCREASES THE MELTING AND ECILIIG POMT and PECREASES THE VAPOUR PRESSURE.To explore this factor properly, a FAIR TEST needs to be conducted. This means that other factors that can affect the IMF strength must be controlled and kept the same. independant variable: (changed on purpose): diffent functional group / different homologous series thuy TYPE of intermolecular force cow differ. dependant variable: (measured during experiment): melting point or boiling point or vapour pressure. controlled variables: (remains the same): ® comparable molecular mass The number of corbow atoms might not alwayy be the same (eg pro~ might be compared with but-) but due to the presence of other atoms the molecular masy of the compuonds will ALWAYS be more-or-less the sounre: © number of branches in the chain (shape of molecule)alkanes, alkenes, alkynes non-polar molecules London force haloalkanes polar molecules dipole-dipole force alcohols polar molecules with O-H Hydrogen bonds ketones, aldehydes polar molecules dipole-dipole force carboxylic acids polar molecules with O-H = Hydrogen bonds (2) esters polar molecules dipole dipole forcesGRAPH OF THE BOILING POINT VS NO. OF CARBON ATOMS FOR DIFFERENT HOMOLOGOUS SERIES. 300 * H-bonds * dipole-dipole 200F * London S = #2 100 = a > Oo carboxylic acids * = ———alconols Ss SS ketones (+ aldehydes) * —o alky ee IKyYNeS lar =190 ack ck eae | atkanes 4 i oO 2 4 6 8 10 Number C-atoms 12 GRAPH ILLUSTRATES TWO TRENDS: * as carbon chain in each family gets longer, BP increases (trend 1) * compounds from different families with same number of carbon atoms have different BP (trend 3)TREND 3: ALKANES vs ALCOLOLS Compounds below: © have the same number of carbons. © are all straight-chained Boiling Boiling point Alkane point (°C) Alcohol (°C) methane - 164 methanol 65 ethane | - 89 _ ethanol | 79 _propane - 42 1-propanol 97 butane - 0.5 1-butanol 117 pentane | 36 _1-pentanol | 138 hexane | 69 _1-hexanol | 156 34, oF 5+ bt 5+ > + 54S b+ St OF alcohol: alkane: very polar part to molecule non polar molecule because of functional group (O-H)The boiling points of alcohols are ALWAYS HIGHER than those of alkanes with comparable molar masses. REASON: Hydrogen bonds between alcohol molecules are stronger than the London forces between alkane molecules. More energy is needed to break the stronger hydrogen bonds between alcohol molecules. alcohol molecules have a O-H in their | ethanol : molecule functional group. | Thus there can be |Weak Van der Waals forces between the non- hydrogen bonds —__-__-+ ™~ polar aly! groups of the between the | alkcohol molecule different molecules ethanol as shown. molecule OH group non-polar alkyl groupTREND % ALKANES vs HALO-ALKANES Halo-alkanes have higher MP and BP than alkanes with a comparable molecular mass (note: number of C atoms different since need to compare similar molecular masses.) butane chloromethane paaeare weak London forces as alkane molecules are tl — tinoh dipole fi completely non polar Stronger dipole-dipole forces ny p between the slightly negative halogen atom and slightly positive Thus, more energy needed hydrogen atoms (polar molecules) to separate molecules causing the higher BP for halo-alkanesTREND 3: ALKANES vs ALDERYDES vs KETONES vé ALCOLOLS Solubility Name Formula Molecular | Boiling point mass (g) "C) in water Butane alkans 0 | Propanai CH,-CH,-C-H 58 49 | aldehyde 4 | Soluble Propanone CHy~¢-CHy 58 | ketone | | sotubie ———atcotrot 7 — a . e "s 1- Propanol | Cc 60 97 | Soluble Aldehydes and ketones have lower boiling points than alcohols of more or less the same molecular mass. This is because they cannot form hydrogen bonds with each other like alcohol molecules do. Aldehydes and ketones can only form dipole-dipole forces between their molecules which are weaker than hydrogen bonds.aldehyde functional group ketone functional group no O-H bonds in the molecules so not as polar as alcohol molecules (therefore can't do hydrogen bonding) dipole-dipole force between 5+ carbon atom of one molecule's carbonyl group and 5- oxygen atom of other molecules carbonyl group. Aldehydes and ketones have higher boiling points than alkanes of similar molecular mass. This is because the intermolecular forces (dipole-dipole) between their molecules are stronger than for alkane molecules (London forces) because of the polar functional group (C=O carbonyl group) on the molecules.3 CARBOXYLIC ACIDS vs... * Carboxylic acids are among the most polar organic compounds because their functional group is made up of two groups: and hydroxyl (which together make a xyl group) ¢ The molecules form strong hydrogen bonds with each other since they can make TWO hydrogen bonds. Two polar groups carboxylic acids therefore have the HIGHEST boiling points out of ALL the compounds we have propanoic acid studied so far. ot pe \ ot —— 5+ fo O—H con 45 2 x hydrogen bonds between the molecules!STANDARD TEMPLATE TO USE WHEN ANSWERING TREND 3 EXPLANATION TYPE QUESTIONS: © First mention the TYPE of intermolecular force present in each of the compounds being compared. © Then compare the strength of each: HYDROGEN BOND > DIPOLE-DIPOLE > LONDON FORCES ¢ As the strength of the intermolecular force increases, * More energy is needed to break them ¢ Melting point / boiling point therefore increase / vapour pressure decreases, When comparing carboxylic acids to alcohols, since both can form hydrogen bonds, need to say that the HYDROGEN BONDS IN CARBOXYLIC ACIDS are STRONGER since 2 hydrogen bonds can form between neighbouring molecules while alcohol molecules can only make 1 hydrogen bond. When comparing the alkanes to the alkenes, since they are both non-polar molecules they both have LONDON FORCES between their molecules. However London forces are stronger in the alkane than the corresponding alkene since alkanes have a slightly bigger molecular mass. (Trend 1)TREND 3 QUESTIONS 1. The boiling points of 1-butanol and propanoic acid are investigated. The results are as follows: IUPAC Molecular Boiling point coe name mass (g-mol"!) (°c) CH3CH,CH;CH,0H _butan-1-ol 74 18 CH3CH,COOH propanoic acid 74 141 1.1 Give an appropriate investigative question. 1.2 Give the independant variable 1.3 Give the dependant variable 1.4 Give the controlled variable 1.5 Write a suitable conclusion to this experiment. 1.6 Give reasons for the conclusion stated in Q 1.5 by referring to the TYPE OF INTERMOLECULAR FORCE, their STRENGTH, and the ENERGY needed for each compound.2. A technician is provided with 3 unmarked bottles, labelled P, Q and R, one of which is an alcohol, one an aldehyde and one an alkane, all with similar molecular masses.. She determines the boiling points of each under the same conditions: SAMPLE BOILING POINT (°C) P 76 Q 36 R 118 2.1 Write a suitable hypothesis. 2.2 Name the independant variable 2.3 Name the dependant variable 2.4 From the passage above, write the phase that indicates that the experiment is a fair test. 2.5 Which compound P, Q or R is an 2.5.1 alkane? 2.5.2 alcohol? 2.6 Refer to the boiling points and the intermolecular force type present in alkanes and alcohols to justify your answer in Q. 2.53. The table below shows the boiling points of two organic compounds, indicated by letters A and B. | Compound | Molecular mass | Boiling point (°C) A | Butane 58 0 Propanal 3.1 Is compound A in gas, liquid or solid phase at 25 °C? 3.2 Compound A has a lower boiling point than B. Give reasons for this variation by referring to POLARITY, TYPE and STRENGTH OF INTERMOLECULAR FORCES and ENERGY involved. 4, Consider the following compounds which belong to different homologous series and have different functional groups. A B c D Compound | CH3CH2CH3, CH3CHO. CHCOOH CH3CHj0H 4.1 Define the concept ‘functional group’. 4.2 Name the homologous series to which A and C belong to. 4.3 Write the structural formula of the functional group for B and D. 4.4 Give the IUPAC name for each of A, B, C and D 4.5 Arrange these four compounds in order of INCREASING boiling point.5. A student performs an experiment to determine the boiling points of different organic substances. The results are shown below: Name Formula a Botta pelnt A | Pentan-1-ol CH3(CH2)4,0H 88 138 B | Pentanal CH3(CHz)3CHO | 88 103 C | Butanoic acid [| CH3(CH2)2CO>H | 88 164 D |Ethyl ethanoate | CH3CO2C2Hs 88 77 [eE [Hexane CH3(CHa)4CH 88 69 5.1 Why must the molecular mass of each compound be kept the same during this experiment? 5.2 To which homologous series do each of A to E belong to? 5.3 Explain the difference in the boiling points of D and E. Refer to the type and strength of intermolecular forces and energy in your answer. 5.4 Explain the differences in the boiling points of A, B and C. Refer to the type and strength of intermolecular forces and energy in your answer. 5.5 Arrange these compounds in order of INCREASING vapour pressure. 5.6 Give a reason for your arrangement in Q 5.5 by referring to the compound's boiling points.6. There are two structural isomers of organic compounds with molecular formua C2H402. 6.1 Define the term structural isomer. 6.2 Write the structural formula of these two isomers and give the IUPAC name of each. 6.3 What type of isomers are these compounds? Give a reason. 6.4 State, with reasons, which ONE of these isomers 6.4.1 has a higher boiling point 6.4.2 has a higher vapour pressure. 6.5 Would the vapour pressure of the carboxylic acids increase or decrease if the number of carbon atoms in the chain increases? 6.6 Give a reason for your answer in Q 6.5 by referring to the type and strength of the IMF's involved.7. Cindy performs an experiment to determine which properties of organic compounds affects vapour pressure. Her results are shown below: Compound Vapour pressure (mm) A_|pentane 400 B | hexane 100 Cc | heptane 40 D_| octane 10 E | 2-methylbutane [450 F | butan-2-one 15 G | butan-2-01 12 H propanoic acid [2 7.1 Define the term vapour pressure. 7.2 What factor should be kept constant when measuring the vapour pressure? Explain why. 7.3 Describe the trend in vapour pressure of compounds A to D. 7.4 Give a reason for your answer in Q 7.3 by referring to the MOLECULAR STRUCTURE, TYPE and STRENGTH of the intermolecular forces. 7.5 The vapour pressure of propanoic acid is lower than that of butan-2-ol which in turn is lower than butan-2-one. Explain this observation by referring to the TYPE and STRENGTH of the intermolecular forces and the ENERGY involved.