Open Question
If someone reported the preparation of a compound with the formula C3H9, most chemists would be skeptical. Why?
Ch.23 - Organic and Biological Chemistry
Chapter 23, Problem 73
Write the open-chain structure of a four-carbon deoxy sugar.
Verified step by step guidance1
Step 1: Understand that a deoxy sugar is a sugar molecule where one of the hydroxyl groups (-OH) is replaced by a hydrogen atom (H).
Step 2: Recognize that a four-carbon sugar is known as a tetrose. The simplest form of a tetrose is an aldotetrose, which has an aldehyde group at one end.
Step 3: Draw the basic structure of an aldotetrose, which includes four carbon atoms in a chain with an aldehyde group (CHO) at the first carbon and hydroxyl groups on the other carbons.
Step 4: Replace one of the hydroxyl groups (-OH) on the carbon chain with a hydrogen atom (H) to create the deoxy sugar. This can be done at any carbon except the one with the aldehyde group.
Step 5: Ensure the structure maintains the correct number of hydrogen atoms and bonds, resulting in a four-carbon deoxy sugar with the general formula C4H8O3.
Related Practice
Open Question
Benzyne, C6H4, is a highly energetic and reactive molecule. The carbon atoms are connected in a six-membered ring. Provide a line drawing for benzyne. What functional group is present?
Open Question
Write the open-chain structure of a ketotetrose.
Open Question
(a) Draw an orbital overlap picture of ethane (CH3CH3), assuming both carbon atoms are sp3 hybridized. What are the C–H bond angles in this drawing? (b) Draw an orbital overlap picture of ethane, assuming both carbon atoms are sp2 hybridized. What are the C–H bond angles in this drawing? (c) The real structure of ethane is like the picture you drew in part (a). Use VSEPR theory to explain why your picture from part (a) makes a more stable molecule than your picture in part (b).
Open Question
Draw an orbital overlap picture of methane (CH₄) with the carbon in sp3 hybridization and an orbital overlap picture of a molecule with carbon in sp2 hybridization. Explain why the carbon atom in methane is more stable in sp3 hybridization than in sp2 hybridization.
Open Question
Unlike palmerolide A (Problem 23.80), which has a large ring, a cyclic molecule with only six atoms can only have a cis double bond, but not a trans double bond. Give a line drawing of a cyclic molecule with six carbon atoms and a cis double bond. Explain why it cannot have a trans double bond.