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 3eb7eb6e6b2e8..754fea85ec6d7 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
@@ -249,6 +249,11 @@ object ReorderAssociativeOperator extends Rule[LogicalPlan] {
     case _ => ExpressionSet(Seq.empty)
   }
 
+  private def isSameInteger(expr: Expression, value: Int): Boolean = expr match {
+    case l: Literal => l.value == value
+    case _ => false
+  }
+
   def apply(plan: LogicalPlan): LogicalPlan = plan.transformWithPruning(
     _.containsPattern(BINARY_ARITHMETIC), ruleId) {
     case q: LogicalPlan =>
@@ -259,32 +264,31 @@ object ReorderAssociativeOperator extends Rule[LogicalPlan] {
       val groupingExpressionSet = collectGroupingExpressions(q)
       q.transformExpressionsDownWithPruning(_.containsPattern(BINARY_ARITHMETIC)) {
       case a @ Add(_, _, f) if a.deterministic && a.dataType.isInstanceOf[IntegralType] =>
-        val (foldables, others) = flattenAdd(a, groupingExpressionSet).partition(_.foldable)
-        if (foldables.nonEmpty) {
-          val foldableExpr = foldables.reduce((x, y) => Add(x, y, f))
-          val foldableValue = foldableExpr.eval(EmptyRow)
+        val (literals, others) = flattenAdd(a, groupingExpressionSet)
+          .partition(_.isInstanceOf[Literal])
+        if (literals.nonEmpty) {
+          val literalExpr = literals.reduce((x, y) => Add(x, y, f))
           if (others.isEmpty) {
-            Literal.create(foldableValue, a.dataType)
-          } else if (foldableValue == 0) {
+            literalExpr
+          } else if (isSameInteger(literalExpr, 0)) {
             others.reduce((x, y) => Add(x, y, f))
           } else {
-            Add(others.reduce((x, y) => Add(x, y, f)), Literal.create(foldableValue, a.dataType), f)
+            Add(others.reduce((x, y) => Add(x, y, f)), literalExpr, f)
           }
         } else {
           a
         }
       case m @ Multiply(_, _, f) if m.deterministic && m.dataType.isInstanceOf[IntegralType] =>
-        val (foldables, others) = flattenMultiply(m, groupingExpressionSet).partition(_.foldable)
-        if (foldables.nonEmpty) {
-          val foldableExpr = foldables.reduce((x, y) => Multiply(x, y, f))
-          val foldableValue = foldableExpr.eval(EmptyRow)
-          if (others.isEmpty || (foldableValue == 0 && !m.nullable)) {
-            Literal.create(foldableValue, m.dataType)
-          } else if (foldableValue == 1) {
+        val (literals, others) = flattenMultiply(m, groupingExpressionSet)
+          .partition(_.isInstanceOf[Literal])
+        if (literals.nonEmpty) {
+          val literalExpr = literals.reduce((x, y) => Multiply(x, y, f))
+          if (others.isEmpty || (isSameInteger(literalExpr, 0) && !m.nullable)) {
+            literalExpr
+          } else if (isSameInteger(literalExpr, 1)) {
             others.reduce((x, y) => Multiply(x, y, f))
           } else {
-            Multiply(others.reduce((x, y) => Multiply(x, y, f)),
-              Literal.create(foldableValue, m.dataType), f)
+            Multiply(others.reduce((x, y) => Multiply(x, y, f)), literalExpr, f)
           }
         } else {
           m
diff --git a/sql/catalyst/src/test/scala/org/apache/spark/sql/catalyst/optimizer/ReorderAssociativeOperatorSuite.scala b/sql/catalyst/src/test/scala/org/apache/spark/sql/catalyst/optimizer/ReorderAssociativeOperatorSuite.scala
index 9090e0c7fc104..7733e58547fe0 100644
--- a/sql/catalyst/src/test/scala/org/apache/spark/sql/catalyst/optimizer/ReorderAssociativeOperatorSuite.scala
+++ b/sql/catalyst/src/test/scala/org/apache/spark/sql/catalyst/optimizer/ReorderAssociativeOperatorSuite.scala
@@ -29,7 +29,8 @@ class ReorderAssociativeOperatorSuite extends PlanTest {
 
   object Optimize extends RuleExecutor[LogicalPlan] {
     val batches =
-      Batch("ReorderAssociativeOperator", Once,
+      Batch("ReorderAssociativeOperator", FixedPoint(10),
+        ConstantFolding,
         ReorderAssociativeOperator) :: Nil
   }
 
@@ -44,7 +45,7 @@ class ReorderAssociativeOperatorSuite extends PlanTest {
           ($"b" + 1) * 2 * 3 * 4,
           $"a" + 1 + $"b" + 2 + $"c" + 3,
           $"a" + 1 + $"b" * 2 + $"c" + 3,
-          Rand(0) * 1 * 2 * 3 * 4)
+          Rand(0) * 1.0 * 2.0 * 3.0 * 4.0)
 
     val optimized = Optimize.execute(originalQuery.analyze)
 
@@ -56,7 +57,7 @@ class ReorderAssociativeOperatorSuite extends PlanTest {
           (($"b" + 1) * 24).as("((((b + 1) * 2) * 3) * 4)"),
           ($"a" + $"b" + $"c" + 6).as("(((((a + 1) + b) + 2) + c) + 3)"),
           ($"a" + $"b" * 2 + $"c" + 4).as("((((a + 1) + (b * 2)) + c) + 3)"),
-          Rand(0) * 1 * 2 * 3 * 4)
+          Rand(0) * 1.0 * 2.0 * 3.0 * 4.0)
         .analyze
 
     comparePlans(optimized, correctAnswer)
@@ -106,4 +107,17 @@ class ReorderAssociativeOperatorSuite extends PlanTest {
 
     comparePlans(optimized, correctAnswer)
   }
+
+  test("SPARK-50380: conditional branches with error expression") {
+    val originalQuery1 = testRelation.select(If($"a" === 1, 1L, Literal(1).div(0) + $"b")).analyze
+    val optimized1 = Optimize.execute(originalQuery1)
+    comparePlans(optimized1, originalQuery1)
+
+    val originalQuery2 = testRelation.select(
+      If($"a" === 1, 1, ($"b" + Literal(Int.MaxValue)) + 1).as("col")).analyze
+    val optimized2 = Optimize.execute(originalQuery2)
+    val correctAnswer2 = testRelation.select(
+      If($"a" === 1, 1, $"b" + (Literal(Int.MaxValue) + 1)).as("col")).analyze
+    comparePlans(optimized2, correctAnswer2)
+  }
 }