Q2P - Organic Chemistry (Mcmurry)

Question

Draw structures corresponding to the following IUPAC names:

1. (Z)-2-Ethyl-2-buten-1-ol
2. 3-Cyclohexen-1-ol
3. trans-3-Chlorocycloheptanol
4. 1,4-Pentanediol
5. 2,6-Dimethylphenol
6. o-(2-Hydroxyethyl)phenol

Step-by-Step Solution

Answer

Answer

Step-by-Step Solution Step 1: Structures of Alcohols and phenols

The alcohol compounds identify by the presence of the R–OH group, whereas phenol compounds identify as Ar–OH (where Ar is an aromatic ring). Firstly, all the attached substituents name according to their alphabet, and the ending occurs by –ol.

Step 2: The structure of (Z)-2-Ethyl-2-buten-1-ol

1. In (Z)-2-Ethyl-2-buten-1-ol, the longest carbon chain that contains an –OH group is 4 carbon chain. The word ‘2-buten’ is used for the double bond at the 2^nd position. The ethyl group (CH₂CH₃) is present at the 2^nd position, and the configuration for the double bond is (Z) means the groups are cis. So, starts numbering from OH containing carbon. Thus, the structure of (Z)-2-Ethyl-2-buten-1-ol is,

                                            (Z)-2-Ethyl-2-buten-1-ol

Step 3: The structure of 3-Cyclohexen-1-ol

b. In 3-Cyclohexen-1-ol, the double bond (C=C) is present at 3^rd position of cyclohexen ring. At the first position, the OH group is present. Thus, the structure of 3-Cyclohexen-1-ol is,

                                 3-Cyclohexen-1-ol

Step 4: The structure of trans-3-Chlorocycloheptanol

c. In trans-3-Chlorocycloheptanol, the chloro group (-Cl) is present at the 3^rd position of the cycloheptane ring. At the first position, the OH group is present. The ‘trans’ means the OH group is above the plane, and the Cl group is below the plane. Thus, the structure of trans-3-Chlorocycloheptanol is,

                             trans-3-Chlorocycloheptanol

Step 5: The structure of 1,4-Pentanediol

d. In 1,4-Pentanediol, the OH groups are present at the 1^st and 4^th position of the longest five-carbon chain. For two OH groups, the diol is used. Thus, the structure of 1,4-Pentanediol is,

                                          1,4-Pentanediol

Step 6: The structure of 2,6-Dimethylphenol

e. In 2,6-Dimethylphenol, draw the phenol ring first and attach two methyl groups () at the 2^nd and 6^th positions, which describes ‘Dimethyl’. Thus, the structure of 2,6-Dimethylphenol is,

                                               2,6-Dimethylphenol

Step 7: The structure of o-(2-Hydroxyethyl)phenol

f. In o-(2-Hydroxyethyl)phenol, first, draw the phenol ring and attach one hydroxyethyl group (-CH₂CH₂OH) at the 2^nd position, which is at the ortho position to the OH of the phenol ring. Thus, the structure of o-(2-Hydroxyethyl)phenol is,

                                    o-(2-Hydroxyethyl)phenol