Introduction to organic chemistry：練習問題

Which of the following represents the correct IUPAC name for the compound with the structural formula \(\text{CH}_3\text{CH(CH}_3\text{)CH(OH)CH}_2\text{CHO}\)?

How many structural isomers with the molecular formula \(\text{C}_4\text{H}_9\text{Br}\) contain a primary carbon bonded to the halogen atom?

Which of the following compounds exhibits E-Z (stereoisomerism)?

Consider the alkene with the structural formula \(\text{CH}_3\text{CH}_2\text{C(CH}_3\text{)=C(Br)CH}_2\text{OH}\).
According to the Cahn–Ingold–Prelog (CIP) priority rules, which statement correctly identifies the higher priority group on each carbon atom of the double bond?

How many structural isomers (including chain, position, and functional group isomers) have the molecular formula \(\text{C}_3\text{H}_6\text{O}_2\) and react with sodium hydrogencarbonate to release carbon dioxide gas?

Give the systematic IUPAC name for the organic compound with the structural formula \(\text{CH}_3\text{CH}(\text{CH}_3)\text{CH}_2\text{CH}(\text{OH})\text{CH}_3\), and state the specific type of structural isomerism shown between this compound and 4-methylpentan-1-ol.

Consider the stereoisomers of 3-methylpent-2-ene.
State the stereochemical descriptor ( extit{E} or extit{Z}) assigned to the isomer in which the \(-\text{CH}_3\) group at carbon-2 and the \(-\text{CH}_2\text{CH}_3\) group at carbon-3 are on the same side of the double bond, and explain your assignment using the Cahn–Ingold–Prelog (CIP) priority rules.

A student investigates four unbranched structural isomers, A, B, C, and D, each having the molecular formula \(\text{C}_5\text{H}_{10}\text{O}\) and containing an unbranched five-carbon chain.

(a) Isomer A is an aldehyde.
(i) Give the IUPAC name for isomer A.
(ii) Draw the skeletal formula of isomer A.

(b) Isomer B and Isomer C are both ketones.
(i) Give the IUPAC name for isomer B and the IUPAC name for isomer C.
(ii) State the type of structural isomerism shown between isomer B and isomer C.

(c) Isomer D is an alkene that contains a primary alcohol group (\(-\text{CH}_2\text{OH}\)) and exhibits stereoisomerism.
(i) State the IUPAC name of isomer D, excluding stereochemical descriptors.
(ii) Explain why isomer D exhibits \(E\)-\(Z\) isomerism.
(iii) Draw the displayed formula of the \((E)\)-isomer of D.
(iv) State the Cahn-Ingold-Prelog (CIP) priority rules and use them to justify why this isomer is assigned the \(E\) configuration.