The correct IUPAC name for the given compound has to be chosen from the given options. Concept Introduction: IUPAC rules for naming alcohols that contain single hydroxyl group: Longest carbon chain has to be identified that contains hydroxyl group also. The chain name is obtained by replacing the letter “-e” in alkane with “-ol”. The numbering has to be given so that the hydroxyl group gets the least numbering. Name and location of any other substituent present in the chain has to be identified. If in a ring the hydroxyl group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering. Hydroxyl group as a substituent in a molecule is named as hydroxy group rather than hydroxyl group. IUPAC rules for naming alcohols that contain more than one hydroxyl group: The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of hydroxyl groups that is present.

Question

a. What is the eluent used in the column chromatography here (a “silica plug filtration” is essentially a very short column)? b. The spectroscopy of compound 5b is described in the second half of this excerpt, including 1H-NMR and 13C-NMR (which you will learn about in CHEM 2412L), MS (which you will learn about later in CHEM 2411L) and IR. One of the IR signals is at 3530 cm-1. What functional group does this indicate might be present in compound 5b?

Answer 1

Question

Chapter 14.3, Problem 4QQ

Interpretation Introduction

Interpretation:

The correct IUPAC name for the given compound has to be chosen from the given options.

Concept Introduction:

IUPAC rules for naming alcohols that contain single hydroxyl group:

Longest carbon chain has to be identified that contains hydroxyl group also. The chain name is obtained by replacing the letter “-e” in alkane with “-ol”.

The numbering has to be given so that the hydroxyl group gets the least numbering.

Name and location of any other substituent present in the chain has to be identified.

If in a ring the hydroxyl group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.

Hydroxyl group as a substituent in a molecule is named as hydroxy group rather than hydroxyl group.

IUPAC rules for naming alcohols that contain more than one hydroxyl group:

The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of hydroxyl groups that is present.

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a. What is the eluent used in the column chromatography here (a “silica plug filtration” is essentially a very short column)? b. The spectroscopy of compound 5b is described in the second half of this excerpt, including 1H-NMR and 13C-NMR (which you will learn about in CHEM 2412L), MS (which you will learn about later in CHEM 2411L) and IR. One of the IR signals is at 3530 cm-1. What functional group does this indicate might be present in compound 5b?

Steps and explanations. Also provide, if possible, ways to adress this kind of problems in general.

a. The first three lines of this procedure describe the reaction used to make compound 5b. In the fourth line, hexane and sodium bicarbonate are added. What organic lab technique is being used here? b. What is the purpose of the Na2SO4? c. What equipment would you use to “concentrate [a solution] under reduced pressure”?