diff --git a/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/optimizer/expressions.scala b/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/optimizer/expressions.scala
index 1d363b8146e3f..cf17f59599968 100644
--- a/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/optimizer/expressions.scala
+++ b/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/optimizer/expressions.scala
@@ -218,15 +218,24 @@ object ReorderAssociativeOperator extends Rule[LogicalPlan] {
 object OptimizeIn extends Rule[LogicalPlan] {
   def apply(plan: LogicalPlan): LogicalPlan = plan transform {
     case q: LogicalPlan => q transformExpressionsDown {
-      case In(v, list) if list.isEmpty && !v.nullable => FalseLiteral
+      case In(v, list) if list.isEmpty =>
+        // When v is not nullable, the following expression will be optimized
+        // to FalseLiteral which is tested in OptimizeInSuite.scala
+        If(IsNotNull(v), FalseLiteral, Literal(null, BooleanType))
       case expr @ In(v, list) if expr.inSetConvertible =>
         val newList = ExpressionSet(list).toSeq
-        if (newList.size > SQLConf.get.optimizerInSetConversionThreshold) {
+        if (newList.length == 1
+          // TODO: `EqualTo` for structural types are not working. Until SPARK-24443 is addressed,
+          // TODO: we exclude them in this rule.
+          && !v.isInstanceOf[CreateNamedStructLike]
+          && !newList.head.isInstanceOf[CreateNamedStructLike]) {
+          EqualTo(v, newList.head)
+        } else if (newList.length > SQLConf.get.optimizerInSetConversionThreshold) {
           val hSet = newList.map(e => e.eval(EmptyRow))
           InSet(v, HashSet() ++ hSet)
-        } else if (newList.size < list.size) {
+        } else if (newList.length < list.length) {
           expr.copy(list = newList)
-        } else { // newList.length == list.length
+        } else { // newList.length == list.length && newList.length > 1
           expr
         }
     }
diff --git a/sql/catalyst/src/test/scala/org/apache/spark/sql/catalyst/optimizer/OptimizeInSuite.scala b/sql/catalyst/src/test/scala/org/apache/spark/sql/catalyst/optimizer/OptimizeInSuite.scala
index 478118ed709f7..86522a6a54ed5 100644
--- a/sql/catalyst/src/test/scala/org/apache/spark/sql/catalyst/optimizer/OptimizeInSuite.scala
+++ b/sql/catalyst/src/test/scala/org/apache/spark/sql/catalyst/optimizer/OptimizeInSuite.scala
@@ -176,6 +176,21 @@ class OptimizeInSuite extends PlanTest {
     }
   }
 
+  test("OptimizedIn test: one element in list gets transformed to EqualTo.") {
+    val originalQuery =
+      testRelation
+        .where(In(UnresolvedAttribute("a"), Seq(Literal(1))))
+        .analyze
+
+    val optimized = Optimize.execute(originalQuery)
+    val correctAnswer =
+      testRelation
+        .where(EqualTo(UnresolvedAttribute("a"), Literal(1)))
+        .analyze
+
+    comparePlans(optimized, correctAnswer)
+  }
+
   test("OptimizedIn test: In empty list gets transformed to FalseLiteral " +
     "when value is not nullable") {
     val originalQuery =
@@ -191,4 +206,21 @@ class OptimizeInSuite extends PlanTest {
 
     comparePlans(optimized, correctAnswer)
   }
+
+  test("OptimizedIn test: In empty list gets transformed to `If` expression " +
+    "when value is nullable") {
+    val originalQuery =
+      testRelation
+        .where(In(UnresolvedAttribute("a"), Nil))
+        .analyze
+
+    val optimized = Optimize.execute(originalQuery)
+    val correctAnswer =
+      testRelation
+        .where(If(IsNotNull(UnresolvedAttribute("a")),
+          Literal(false), Literal.create(null, BooleanType)))
+        .analyze
+
+    comparePlans(optimized, correctAnswer)
+  }
 }