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The table shows the boiling points of four primary alcohols and two secondary alcohols - Leaving Cert Chemistry - Question 8 - 2019

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The table shows the boiling points of four primary alcohols and two secondary alcohols. (a) (i) What is a secondary alcohol? (ii) On the same sheet of graph paper ... show full transcript

Worked Solution & Example Answer:The table shows the boiling points of four primary alcohols and two secondary alcohols - Leaving Cert Chemistry - Question 8 - 2019

Step 1

What is a secondary alcohol?

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Answer

A secondary alcohol is an alcohol in which the hydroxyl (OH) group is attached to a carbon atom that is itself attached to two other carbon atoms. This means that in a secondary alcohol, the carbon with the OH group is connected to two additional carbon chains.

Step 2

On the same sheet of graph paper and using the same pair of axes, plot the boiling points of these alcohols against the number of carbon atoms present.

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Answer

To plot the boiling points, use a graph with the x-axis representing the number of carbon atoms (from 1 to 4) and the y-axis as the boiling points in °C. Each alcohol's boiling point is marked according to its respective number of carbon atoms. For example, methanol (1C) at 64.7°C, ethanol (2C) at 78.4°C, propan-1-ol (3C) at 97.2°C, butan-1-ol (4C) at 117.5°C, butan-2-ol (4C) at 99.1°C.

Step 3

State and explain the trend in the boiling points of the four primary alcohols shown as their relative molecular masses increase.

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The trend is that the boiling points of the primary alcohols increase as their relative molecular masses increase. This is primarily due to the increased van der Waals forces between the molecules. As the molecular mass increases, there are more electrons present, leading to stronger dispersion forces which require more energy (in the form of heat) to break during boiling.

Step 4

Predict the approximate boiling point of the next alcohol in the same series as propan-2-ol and butan-2-ol.

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The next alcohol in the series after propan-2-ol and butan-2-ol would be pentan-2-ol. Given the rising trend of boiling points, one can predict that pentan-2-ol would have a boiling point around 120–125°C.

Step 5

Give the systematic IUPAC names for the two possible organic products.

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The two possible organic products from the oxidation of an alcohol where no carbon-carbon bonds are broken are:

  1. Butanal (an aldehyde)
  2. Butan-2-one (a ketone).

Step 6

Draw the structure of the organic product when butan-2-ol is oxidised in this way.

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The structure of the organic product, butan-2-one, is as follows:

     CH3
      |
CH3-C-CHO  (Butanal)
      |
     OH

Butan-2-one is shown above as having a carbonyl group (C=O) where the alcohol was oxidised.

Step 7

Identify clearly which bonds in butan-2-ol are broken in this oxidation.

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In the oxidation of butan-2-ol, the C-H bonds adjacent to the hydroxyl carbon (the carbon attached to the OH group) are broken. Specifically, the bond between the hydroxyl carbon and one of its attached hydrogen atoms is broken.

Step 8

Draw the structure of this ester.

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Answer

The structure of the ester formed from methanol and propanoic acid is:

   O  
   ||   
CH3-C-O-CH2-CH2-COOH 

This representation shows the ester functional group (-COO-) formed by the reaction.

Step 9

How many carbon atoms in a molecule of this ester are tetrahedrally bonded?

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In the molecule of the ester formed from methanol and propanoic acid, there are a total of 4 carbon atoms that are tetrahedrally bonded. This includes the carbon in the hydroxyl group and the carbon in the carbonyl group.

Step 10

What are the products of the hydrolysis of this ester by NaOH?

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Answer

The hydrolysis of the ester by NaOH produces methanol and sodium propanoate (or sodium propionate). This can be represented as:

ester + NaOH → methanol + sodium propanoate

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