Naming Aldehydes and Ketones
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1 Assignment 4 Task 3 Due: 11:59pm on Friday, October 5, 2018 You will receive no credit for items you complete after the assignment is due. Grading Policy Naming Aldehydes and Ketones The International Union of Pure and Applied Chemistry (IUPAC) determines the system for naming compounds. For compounds other than alkanes, the longest chain will be named like an alkane, but with the e replaced with a few letters that indicate a functional group. In the case of aldehydes and ketones, these letters are al and one, respectively. C atoms Alkane Aldehyde Ketone 1 methane methanal methanone 2 ethane ethanal ethanone 3 propane propanal propanone 4 butane butanal butanone 5 pentane pentanal pentanone 6 hexane hexanal hexanone 7 heptane heptanal heptanone 8 octane octanal octanone Part A Name the aldehyde displayed below. Enter the name. Hint 1. How to approach the problem 1. Name the longest carbon chain by replacing the e in the alkane name with an al. 2. Name and number substituents as usual by numbering the carbon atoms from the carbonyl carbon, which is number one. Hint 2. Determine the number of carbon atoms in the longest chain How many carbon atoms are shown in the longest chain?. Express your answer numerically as an integer. Hint 1. How to interpret the line-bond formula Corners and ends of lines in a line-bond formula represent carbon atoms unless otherwise specified by a chemical symbol. 7 Hint 3. How to name a substituent on an aldehyde Carbon atoms in the longest chain are numbered from the carbonyl carbon, which is number one. Substituents are named with a number corresponding to the number of the carbon atom to which they are bonded. If the substituent is another carbon chain, the name is the alkane name with the e replaced with yl. If the substituent is a halogen, the name is the element name with the ine replaced with o. Hint 4. Number the substituent of the aldehyde Select the correct number of the halide substituent. 1/6
2 first second third The bromo- group is on the fourth fifth sixth seventh carbon atom. 5-bromoheptanal Part B The ketone displayed below could potentially have any of the names listed. Choose the name that follows IUPAC guidelines. Hint 1. How to approach the problem The best method to determine which name is correct is to name the ketone yourself. Follow the steps below to name the ketone. 1. Name the longest chain of carbon atoms by replacing the e in the alkane name with one. If the ketone is attached to a ring, the prefix cyclo- is attached to the alkane name. 2. Number the carbon chain from the end nearest the ketone, and precede the name of the longest carbon chain with the number of the carbonyl carbon. If the ketone is in a ring, the carbon atoms are numbered with the carbonyl carbon as number one. 3. Name and number any substituents. Hint 2. Determine the alkane name of the longest carbon chain Select the name of the longest chain in the ketone below. Hint 1. How to interpret line-bond formulas Recall that corners and ends of lines in line-bond formulas represent carbon atoms unless otherwise specified by a chemical symbol. hexanone heptanone octanone nonanone Hint 3. How to name a substituent on a ketone Carbon atoms in the longest chain are numbered from the end closest to the carbonyl carbon. Substituents are named with a number corresponding to the number of the carbon atom to which they are bonded. 2/6
3 If the substituent is another carbon chain, the name is the alkane name with the e replaced with yl. If the substituent is a halogen, the name is the element name with the ine replaced with o. Hint 4. Number the groups in the molecule This molecule contains a ketone group on the carbon atom and a(n) group on the carbon atom. Select the answer that correctly fills the blanks in order. fifth / ethyl / second third / methyl / sixth third / ethyl / sixth sixth / methyl / third 3-methyl-6-octanone 6-ethyl-3-heptanone 6-methyl-3-octanone 2-ethyl-5-heptanone 6-ethyl-6-methyl-3-hexanone It is often possible to name a compound in different ways. IUPAC guidelines provide a common method for naming so that we can more easily understand each other. Nomenclature: Draw the structure of enol tautomer of cyclopentanone Part A Draw the structural formula of the enol tautomer of cyclopentanone. Draw the molecule on the canvas by choosing buttons from the Tools (for bonds), Atoms, and Advanced Template toolbars. The single bond is active by default. 3/6
4 Excellent! Problem Within each set of structures, indicate which will react fastest, and which slowest, toward nucleophilic addition in basic conditions. Part A Drag the appropriate labels to their respective targets. 4/6
5 Reset Help Fastest Slowest Slowest Fastest Part B Drag the appropriate labels to their respective targets. Reset Help Fastest Slowest Fastest Slowest 5/6
6 Part C Drag the appropriate labels to their respective targets. Reset Help Fastest Slowest Fastest Slowest Score Summary: Your score on this assignment is 100%. You received 3 out of a possible total of 3 points. 6/6
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