2.5_Organic_AS91165

=Demonstrate understanding the properties of selected organic compounds (4 credits) =

__STRUCTURAL FORMULA __
==NCEA PAST EXAM QUESTION: Draw the structural formula (aka displayed or expanded structural formula) for the following organic substances ==

The table below provides an overview of the names of the organic substance and year that they appeared in the NCEA Exam paper


Additional questions on structural formula

====The organic compound, 4-chloro-3-methylpent-4-ene has been named incorrectly. Draw the implied structure and explain why it is named incorrectly. The correct IUPAC name for this structure is: ==== ====Draw the structural formula for every organic substance named in the table above, you may find it useful to print the questions where there is space provided to draw the diagrams. Also, name the homologous series that the substance is in.====

====Print a table of questions on structural formula that have __not yet__ appeared in the NCEA Exams... complete the table and mark it yourself using the answers provided. ==== 

NCEA PAST EXAM QUESTION: Write the IUPAC (systematic) names for the following organic substances


ADDITIONAL NCEA PAST EXAM QUESTIONS on IUPAC naming


[[image:crystalball.gif align="left"]]
====Print a table of questions on IUPAC naming that have __not yet__ appeared in the NCEA Exams... complete the table and mark it yourself using the answers provided. ====

NCEA PAST EXAM QUESTIONS on structural and geometric isomers


<span style="font-family: Arial,Helvetica,sans-serif;">• explain the requirements for geometric (cis and trans) isomers by referring to compounds A, B, and C.
<span style="color: #f95725; font-family: Arial,Helvetica,sans-serif;">

<span style="font-family: Arial,Helvetica,sans-serif;">ii) Draw the geometric isomers of this molecule in the table below.
====<span style="font-family: Arial,Helvetica,sans-serif;">(c) Discuss why the organic molecule C2H4Cl2 forms structural isomers but does not form geometric isomers whereas the molecule C2H2Cl2 forms both structural AND geometric isomers. ====

<span style="font-family: Arial,Helvetica,sans-serif;">In your answer, you must include:

 * ====<span style="font-family: Arial,Helvetica,sans-serif;">a description of each type of isomer (geometric or structural) ====
 * ====<span style="font-family: Arial,Helvetica,sans-serif;">the characteristics of molecules that form these types of isomer ====
 * ====<span style="font-family: Arial,Helvetica,sans-serif;">the structural formulae and functional groups of both C2H4Cl2 AND C2H2Cl2. ====

<span style="font-family: Arial,Helvetica,sans-serif;">• reference to the structure of the selected molecule
<span style="font-family: Arial,Helvetica,sans-serif; line-height: 0px; overflow: hidden;">

<span style="font-family: Arial,Helvetica,sans-serif;">(b) Explain why the compounds you have selected are structural isomers.
<span style="font-family: Arial,Helvetica,sans-serif;">and

<span style="font-family: Arial,Helvetica,sans-serif;">(b) Draw the cis and trans isomers of the compound you circled in (a).
====<span style="font-family: Arial,Helvetica,sans-serif;">(c) Discuss the requirements for cis-trans isomerism. In your answer include reasons explaining why the structural isomer you selected above can exist as cis-trans isomers while the other structural isomer cannot. ==== <span style="font-family: Arial,Helvetica,sans-serif;">

<span style="font-family: Arial,Helvetica,sans-serif;">(b) But–2–ene can exist as geometric (cis–trans) isomers, whereas but–1–ene cannot. Explain this difference.


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__<span style="color: #f95725; font-family: Arial,Helvetica,sans-serif;">MAJOR AND MINOR PRODUCTS OF ADDITION TO ALKENES __
<span style="color: #f95725; font-family: Arial,Helvetica,sans-serif;">NCEA PAST EXAM QUESTIONS on Major and minor products of addition to alkenes

<span style="font-family: Arial,Helvetica,sans-serif;">Explain why Reaction 1 forms only a single organic product, but Reaction 2 forms a mixture of organic products.
<span style="color: #f95725; font-family: Arial,Helvetica,sans-serif;">

For the following reaction:
<span style="color: #000000; font-family: 'Times New Roman','serif'; font-size: 16px;">

__ POLMERISATION OF ALKENES __

 * [[image:l2polymer.jpg width="432" height="240" link="@http://highered.mcgraw-hill.com/sites/0072410159/student_view0/chapter9/figures_alive_.html"]] || [[image:makingpolypropene.jpg width="564" height="371" link="@file:makingpolypropene.pdf"]] ||

<span style="font-family: Arial,Helvetica,sans-serif;">Cling Wrap is a polymer that can be made from the monomer 1,1-dichloroethene. Draw THREE repeating units of the polymer formed.
<span style="color: #221e1f; font-family: 'Times New Roman',serif; font-size: 15.3333px;">
 * ====[[image:2014polymer.jpg width="256" height="275"]]==== || ====[[image:2014polyme2r.jpg]]==== ||

i <span style="font-family: Arial,Helvetica,sans-serif;">) Draw TWO repeating units of the polymer formed in reaction 5
====<span style="font-family: Arial,Helvetica,sans-serif;">ii) Compare and contrast the polymer formed in reaction 5 to the polymer formed in the first reaction. In your answer you should explain why the polymers formed in these two reactions are different. ====

**i)** The molecule tetrafluoroethene, shown below, is the monomer for the polymer commonly known as Teflon.
CF 2  =CF  2

Draw two repeating units of the polymer formed from but-1-ene
**and** ====<span style="font-family: Arial,Helvetica,sans-serif;">The following diagram shows four repeating sections of the polymer commonly called polypropene. Draw the structural formula of the monomer molecule used to make this polymer. ==== <span style="font-family: Arial,Helvetica,sans-serif;"> ====<span style="font-family: Arial,Helvetica,sans-serif;">The molecule undergoes an addition polymerisation reaction to form a polymer. Draw THREE repeating units for the polymer made from this molecule. ====

ii) The molecule 2-methyl propenoate, shown below, is the monomer for the polymer commonly known as Perspex. Draw the structural formula of the polymer Perspex showing TWO repeating units.
====<span style="font-family: Arial,Helvetica,sans-serif;">The following diagram shows four repeating sections of the polymer commonly known as PVC. Draw the structural formula for the monomer molecule used to make this polymer. ====

<span style="font-family: Arial,Helvetica,sans-serif;">Complete the table below by drawing the structural formula of the monomer or polymer (showing two repeating units).
====<span style="font-family: Arial,Helvetica,sans-serif;">Two common polymers are polypropylene and polyvinyl chloride (PVC). A section of each polymer is shown in the table below. Draw the structural formula for the monomer molecule for each polymer. ====

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<span style="color: #f95725; font-family: Arial,Helvetica,sans-serif;">NCEA PAST EXAM QUESTIONS on primary, secondary and tertiary haloalkanes and alcohols
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Draw a primary, a secondary, and a tertiary alcohol for the molecule C5H11OH.
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<span style="font-family: Arial,Helvetica,sans-serif;">(a) Describe why both these molecules can be classified as tertiary.
====<span style="font-family: Arial,Helvetica,sans-serif;">(b) Explain why Molecule 1 and Molecule 2 are not structural isomers of each other. In your answer, you should outline what a structural isomer is, and refer to both molecules. ====

<span style="font-family: Arial,Helvetica,sans-serif;">(c) Draw a structural isomer of Molecule 1
<span style="font-family: Arial,Helvetica,sans-serif;">

<span style="font-family: Arial,Helvetica,sans-serif;">Classify each of the following alcohols as primary, secondary or tertiary and explain your answer for each substance
<span style="font-family: Arial,Helvetica,sans-serif; line-height: 0px; overflow: hidden;">

Vitamin C has the following structure. <span style="font-family: Arial,Helvetica,sans-serif;">Classify the –OH groups labelled A and B as primary, secondary or tertiary.


====<span style="font-family: Arial,Helvetica,sans-serif;">Four alcohols with the same molecular formula are shown in the table below. Complete the table by classifying each alcohol as primary, secondary or tertiary. ====

<span style="font-family: Arial,Helvetica,sans-serif;">(a) On the molecule circle the section that is an alkene and would readily react to decolourise bromine water.
====<span style="font-family: Arial,Helvetica,sans-serif;">(b) Two of the -OH groups in the molecule have been labelled as (A) and (B). Classify these -OH groups as primary, secondary or tertiary alcohol groups. ====



<span style="font-family: Arial,Helvetica,sans-serif;">

** iii) ** Complete the equation below to show the structural formula of the organic product formed.




<span style="font-family: Arial,Helvetica,sans-serif;">Draw and name the product and type of reaction when propanoic acid is reacted with sodium hydroxide solution.


==<span style="font-family: Arial,Helvetica,sans-serif;"> <span style="color: #f95725; font-family: Arial,Helvetica,sans-serif;"> NCEA PAST EXAM QUESTIONS on tests to identify organic substances ==



You do not need to include equations in your answer.
<span style="color: #f95725; font-family: Arial,Helvetica,sans-serif;">

<span style="font-family: Arial,Helvetica,sans-serif;">(a) Five colourless organic solutions that have no labels on the their bottles are known to be:

 * ====<span style="font-family: Arial,Helvetica,sans-serif;">ethanoic acid ====
 * ====<span style="font-family: Arial,Helvetica,sans-serif;">aminoethane ====
 * ====<span style="font-family: Arial,Helvetica,sans-serif;">ethanol ====
 * ====<span style="font-family: Arial,Helvetica,sans-serif;">hexane ====
 * ====<span style="font-family: Arial,Helvetica,sans-serif;">hex-1-ene. ====

<span style="font-family: Arial,Helvetica,sans-serif;">In your answer, you must include a coherent scheme that would allow another student to follow your method, along with:

 * ====<span style="font-family: Arial,Helvetica,sans-serif;">the reagent used ====
 * ====<span style="font-family: Arial,Helvetica,sans-serif;">observations ====
 * ====<span style="font-family: Arial,Helvetica,sans-serif;">chemical equations that show the species reacting and products formed. ====

hexane hex–1–ene
====Both compounds will react with bromine (Br2), but under different conditions. Discuss how the reactions with bromine could be used to distinguish between <span style="font-family: Arial,Helvetica,sans-serif;">hexane and hex–1–ene. ==== ====In your answer include a description of expected observations, the conditions necessary for a reaction to occur, the type of reaction occurring and explanation for this, relevant equations and names of any products formed.====

<span style="font-family: Arial,Helvetica,sans-serif;">(iii) clearly explain how the test results can be used to distinguish between them and why the test used is a suitable one.




==<span style="font-family: Arial,Helvetica,sans-serif;"> <span style="color: #f95725; font-family: Arial,Helvetica,sans-serif;">NCEA EXAM QUESTIONS ON Types of Organic Reactions == <span style="color: #f95725; font-family: Arial,Helvetica,sans-serif;">

[[image:2014organictypes2.jpg width="200" height="102"]]
<span style="color: #f95725; font-family: Arial,Helvetica,sans-serif;">

<span style="font-family: Arial,Helvetica,sans-serif;">For each reaction, your answer should include: the type of reaction occurring and the reason why it is classified as that type
<span style="color: #f95725; font-family: Arial,Helvetica,sans-serif;"> Chloroethane, CH3CH2Cl, reacts with aqueous KOH, alcoholic KOH, and with NH3. Compare and contrast the reactions of chloroethane with the three reagents. In your answer you should include:

<span style="font-family: Arial,Helvetica,sans-serif;">Allocate these reaction types to each of the four reactions
====<span style="font-family: Arial,Helvetica,sans-serif;">**ii)** Compare and contrast the similarities and differences between addition, elimination, and substitution reactions. You should use the examples of the reactions above in your answer ====
 * ====<span style="font-family: Arial,Helvetica,sans-serif;">1) ==== || ====<span style="font-family: Arial,Helvetica,sans-serif;">CH3–CH2–CH2–OH --> C3H7Cl ==== || ====<span style="font-family: Arial,Helvetica,sans-serif;">Reaction type: ==== ||
 * ====<span style="font-family: Arial,Helvetica,sans-serif;">2) ==== || ====<span style="font-family: Arial,Helvetica,sans-serif;">C3H7Cl --> CH3–CH2–CH2–NH2 ==== || ====<span style="font-family: Arial,Helvetica,sans-serif;">Reaction type: ==== ||
 * ====<span style="font-family: Arial,Helvetica,sans-serif;">3) ==== || ====<span style="font-family: Arial,Helvetica,sans-serif;">CH3–CH2–CH2–OH --> C3H6 ==== || ====<span style="font-family: Arial,Helvetica,sans-serif;">Reaction type: ==== ||
 * ====<span style="font-family: Arial,Helvetica,sans-serif;">4) ==== || ====<span style="font-family: Arial,Helvetica,sans-serif;">C3H6 --> C3H7Cl ==== || ====<span style="font-family: Arial,Helvetica,sans-serif;">Reaction type: ==== ||

<span style="font-family: Arial,Helvetica,sans-serif;">• Write the structural formula of the organic product formed.
====<span style="color: #221e1f; font-family: 'Times New Roman','serif'; font-size: 16px;">• <span style="font-family: Arial,Helvetica,sans-serif;">elimination __or__ addition __or__ oxidation __or__ substitution __or__ hydrolysis __or__ halogenation __or__ acid-base ====

i)
<span style="display: block; font-family: Arial,Helvetica,sans-serif; text-align: left;">ii) iii) ====<span style="font-family: Arial,Helvetica,sans-serif;">2) Hydrocarbons can undergo addition and substitution reactions. Compare and contrast addition and substitution reactions. Use the reactions of ethane, CH3– CH3, and ethene, CH2= CH2, with chlorine as your examples in your answer. ====

<span style="font-family: Arial,Helvetica,sans-serif;">• equations showing the structural formulae of the organic reactant(s) and product(s).
<span style="font-family: Arial,Helvetica,sans-serif;">

<span style="font-family: Arial,Helvetica,sans-serif;">1) (i) Write the IUPAC name or the structural formula of the product formed.
====<span style="font-family: Arial,Helvetica,sans-serif;">(ii) State the type of reaction occurring. Choose from the following words: acid-base or addition or elimination or hydrolysis or oxidation or polymerisation or substitution ====

<span style="font-family: Arial,Helvetica,sans-serif;">• type of reaction occurring.
====<span style="font-family: Arial,Helvetica,sans-serif;">Some reactions involving organic compounds can be classified as addition or elimination. Use the examples (a) and (b) given below to clearly explain the type of reaction involved: ====

<span style="font-family: Arial,Helvetica,sans-serif;">(a) When HCl reacts with but–1–ene an addition reaction occurs.
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<span style="font-family: Arial,Helvetica,sans-serif;">(b) When ethanol is heated with concentrated sulphuric acid an elimination reaction occurs.
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<span style="font-family: Arial,Helvetica,sans-serif;"> <span style="font-family: Arial,Helvetica,sans-serif;"> <span style="font-family: Arial,Helvetica,sans-serif; line-height: 0px; overflow: hidden;">

[[image:printButton.gif link="@file:1steporganic.docx"]]<span style="color: #f95725; font-family: Arial,Helvetica,sans-serif;">NCEA EXAM QUESTIONS on mostly one step organic reactions
<span style="color: #f95725; font-family: Arial,Helvetica,sans-serif;"> <span style="color: #0f0101; font-family: Arial,Helvetica,sans-serif;">1. <span style="color: #f95725; font-family: Arial,Helvetica,sans-serif;">

<span style="font-family: Arial,Helvetica,sans-serif;">Analyse BOTH of these reactions by:
<span style="font-family: Arial,Helvetica,sans-serif;">2.
 * ====<span style="font-family: Arial,Helvetica,sans-serif;">describing the reagents and conditions needed for each reaction to occur ====
 * ====<span style="font-family: Arial,Helvetica,sans-serif;">identifying each type of reaction and explaining your choice ====

Ethene, C 2 H 4 (//g//), reacts with aqueous potassium permanganate solution, KMnO 4 (//aq//), dilute acid, H 2 O / H +, and hydrogen bromide, HBr.
Compare and contrast the reactions of ethene gas with each of these three reagents. In your answer, you should: • describe any observations that can be made • identify, with reasons, the type of reaction ethene undergoes with each reagent • describe the functional group of the products formed • include equations showing the structural formulae for the organic compounds for each reaction. <span style="color: #f95725; font-family: Arial,Helvetica,sans-serif;"> ====<span style="font-family: Arial,Helvetica,sans-serif;">i) When primary alcohols are oxidised by acidified permanganate, MnO4–/ H+, they form carboxylic acids. Draw the primary alcohol that was oxidised to form the carboxylic acid shown. ====

<span style="font-family: Arial,Helvetica,sans-serif;">ii) Describe the colour change that would be observed.
====<span style="font-family: Arial,Helvetica,sans-serif;">iii) One of the other alcohol isomers of C4H10O can also be oxidised to form a carboxylic acid. Identify this isomer by name or structural formula: Explain your choice of isomer. ====

<span style="font-family: Arial,Helvetica,sans-serif;">(ii) Ethanoic acid, CH3COOH, reacts with sodium carbonate solution.
====<span style="font-family: Arial,Helvetica,sans-serif;">(iii) One of the isomers of C4H8 can be oxidised with potassium permanganate, <span style="font-family: Arial,Helvetica,sans-serif;">KMnO4, to form 2-methylpropan-1,2-diol. Complete the following equation to show the structural formula of the isomer of C4H8 ==== ====<span style="font-family: Arial,Helvetica,sans-serif;">(iv) 2-methyl propan-1,2-diol can be further oxidised with acidified potassium dichromate, Cr2O72– / H+, to form a compound with molecular formula C4H8O3. The compound C4H8O3 reacts with sodium carbonate solution to form bubbles of carbon dioxide gas. Draw the structural formula of the compound C4H8O3. ====

<span style="font-family: Arial,Helvetica,sans-serif;">1) Complete the following reactions by writing the structural formula of each organic product.
<span style="font-family: Arial,Helvetica,sans-serif;">i)

<span style="font-family: Arial,Helvetica,sans-serif;"> <span style="font-family: Arial,Helvetica,sans-serif;">ii) <span style="font-family: Arial,Helvetica,sans-serif;"> <span style="font-family: Arial,Helvetica,sans-serif;"> iii) <span style="font-family: Arial,Helvetica,sans-serif;"> 2) Methylpropene can be formed from methylpropan–2–ol. Identify a reagent that can be used to do this.

<span style="font-family: Arial,Helvetica,sans-serif;">Complete the following equations by drawing the structural formula of the organic products in the boxes provided.
<span style="font-family: Arial,Helvetica,sans-serif;">i) ii)

<span style="font-family: Arial,Helvetica,sans-serif;">(ii) Describe what would be observed when this reaction occurs.
<span style="font-family: Arial,Helvetica,sans-serif;"> <span style="font-family: Arial,Helvetica,sans-serif;">



==<span style="font-family: Arial,Helvetica,sans-serif;"> <span style="color: #f95725; font-family: Arial,Helvetica,sans-serif;">NCEA EXAM QUESTIONS on Organic Flowcharts ==

<span style="color: #f95725; font-family: Arial,Helvetica,sans-serif;">

[[image:Level 2 Organic types.jpg width="793" height="500" link="@file:Level 2 Organic types.pdf"]]
====Print out these flowcharts onto paper and stick onto your study wall or toilet door, you need a really clear picture in your head of these reactions. Even better....write and draw out your own flowchart summary.====



<span style="font-family: Arial,Helvetica,sans-serif;">(iii) Identify reagents X and Y.
<span style="font-family: Arial,Helvetica,sans-serif;">The reactions shown below are all classified as being the same type of reaction.

<span style="font-family: Arial,Helvetica,sans-serif;">**1)** The flow diagram below shows a reaction scheme for the conversion of but-1-ene into but-2-ene.
<span style="font-family: Arial,Helvetica,sans-serif; line-height: 0px; overflow: hidden;">

• the structural formula of the **organic** product.
<span style="color: #f95725; font-family: Arial,Helvetica,sans-serif; line-height: 0px; overflow: hidden;"> But-1-ene is used in the reaction sequence shown below.

<span style="font-family: Arial,Helvetica,sans-serif;">The flow diagram below shows a series of organic reactions.
====<span style="font-family: Arial,Helvetica,sans-serif;">Complete the diagram by drawing structural formulae and writing IUPAC (systematic) names for the compounds A, B and C (which turns litmus red) and identifying reagent D ====

====<span style="font-family: Arial,Helvetica,sans-serif;">An unsaturated compound A, C3H6, reacts with water under acidic conditions to form two new products, B and C. Product B reacts with acidified potassium dichromate solution to form D. Product D reacts with a solution of sodium carbonate producing bubbles of gas. ====

<span style="font-family: Arial,Helvetica,sans-serif;">Write down the structural formula and name for each compound A, B, C and D
.<span style="font-family: Arial,Helvetica,sans-serif;"> <span style="font-family: Arial,Helvetica,sans-serif;">



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 * = [[image:l2scipadexternal.jpg width="226" height="318" link="@http://www.scipad.co.nz/Digital/Year%2012%20Chemistry%20Externals%20digital/Level%202%20Chemistry%20%28Ext%29.html"]]