diff --git a/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/expressions/Canonicalize.scala b/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/expressions/Canonicalize.scala
index 07ba7d5e4a8493607cfd5c51a434b06015072a36..e876450c73fde0c77fc7671e326b30dcf8ae69fe 100644
--- a/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/expressions/Canonicalize.scala
+++ b/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/expressions/Canonicalize.scala
@@ -62,6 +62,13 @@ object Canonicalize extends {
     case a: Add => orderCommutative(a, { case Add(l, r) => Seq(l, r) }).reduce(Add)
     case m: Multiply => orderCommutative(m, { case Multiply(l, r) => Seq(l, r) }).reduce(Multiply)
 
+    case o: Or =>
+      orderCommutative(o, { case Or(l, r) if l.deterministic && r.deterministic => Seq(l, r) })
+        .reduce(Or)
+    case a: And =>
+      orderCommutative(a, { case And(l, r) if l.deterministic && r.deterministic => Seq(l, r)})
+        .reduce(And)
+
     case EqualTo(l, r) if l.hashCode() > r.hashCode() => EqualTo(r, l)
     case EqualNullSafe(l, r) if l.hashCode() > r.hashCode() => EqualNullSafe(r, l)
 
diff --git a/sql/catalyst/src/test/scala/org/apache/spark/sql/catalyst/expressions/ExpressionSetSuite.scala b/sql/catalyst/src/test/scala/org/apache/spark/sql/catalyst/expressions/ExpressionSetSuite.scala
index 60939ee0eda5d10e215133661d221b64930b4fcf..c587d4f6325313c8335e6fa3ea438702a4f0b6f2 100644
--- a/sql/catalyst/src/test/scala/org/apache/spark/sql/catalyst/expressions/ExpressionSetSuite.scala
+++ b/sql/catalyst/src/test/scala/org/apache/spark/sql/catalyst/expressions/ExpressionSetSuite.scala
@@ -80,6 +80,88 @@ class ExpressionSetSuite extends SparkFunSuite {
   setTest(1, Not(aUpper >= 1), aUpper < 1, Not(Literal(1) <= aUpper), Literal(1) > aUpper)
   setTest(1, Not(aUpper <= 1), aUpper > 1, Not(Literal(1) >= aUpper), Literal(1) < aUpper)
 
+  // Reordering AND/OR expressions
+  setTest(1, aUpper > bUpper && aUpper <= 10, aUpper <= 10 && aUpper > bUpper)
+  setTest(1,
+    aUpper > bUpper && bUpper > 100 && aUpper <= 10,
+    bUpper > 100 && aUpper <= 10 && aUpper > bUpper)
+
+  setTest(1, aUpper > bUpper || aUpper <= 10, aUpper <= 10 || aUpper > bUpper)
+  setTest(1,
+    aUpper > bUpper || bUpper > 100 || aUpper <= 10,
+    bUpper > 100 || aUpper <= 10 || aUpper > bUpper)
+
+  setTest(1,
+    (aUpper <= 10 && aUpper > bUpper) || bUpper > 100,
+    bUpper > 100 || (aUpper <= 10 && aUpper > bUpper))
+
+  setTest(1,
+    aUpper >= bUpper || (aUpper > 10 && bUpper < 10),
+    (bUpper < 10 && aUpper > 10) || aUpper >= bUpper)
+
+  // More complicated cases mixing AND/OR
+  // Three predicates in the following:
+  //   (bUpper > 100)
+  //   (aUpper < 100 && bUpper <= aUpper)
+  //   (aUpper >= 10 && bUpper >= 50)
+  // They can be reordered and the sub-predicates contained in each of them can be reordered too.
+  setTest(1,
+    (bUpper > 100) || (aUpper < 100 && bUpper <= aUpper) || (aUpper >= 10 && bUpper >= 50),
+    (aUpper >= 10 && bUpper >= 50) || (bUpper > 100) || (aUpper < 100 && bUpper <= aUpper),
+    (bUpper >= 50 && aUpper >= 10) || (bUpper <= aUpper && aUpper < 100) || (bUpper > 100))
+
+  // Two predicates in the following:
+  //   (bUpper > 100 && aUpper < 100 && bUpper <= aUpper)
+  //   (aUpper >= 10 && bUpper >= 50)
+  setTest(1,
+    (bUpper > 100 && aUpper < 100 && bUpper <= aUpper) || (aUpper >= 10 && bUpper >= 50),
+    (aUpper >= 10 && bUpper >= 50) || (aUpper < 100 && bUpper > 100 && bUpper <= aUpper),
+    (bUpper >= 50 && aUpper >= 10) || (bUpper <= aUpper && aUpper < 100 && bUpper > 100))
+
+  // Three predicates in the following:
+  //   (aUpper >= 10)
+  //   (bUpper <= 10 && aUpper === bUpper && aUpper < 100)
+  //   (bUpper >= 100)
+  setTest(1,
+    (aUpper >= 10) || (bUpper <= 10 && aUpper === bUpper && aUpper < 100) || (bUpper >= 100),
+    (aUpper === bUpper && aUpper < 100 && bUpper <= 10) || (bUpper >= 100) || (aUpper >= 10),
+    (aUpper < 100 && bUpper <= 10 && aUpper === bUpper) || (aUpper >= 10) || (bUpper >= 100),
+    ((bUpper <= 10 && aUpper === bUpper) && aUpper < 100) || ((aUpper >= 10) || (bUpper >= 100)))
+
+  // Don't reorder non-deterministic expression in AND/OR.
+  setTest(2, Rand(1L) > aUpper && aUpper <= 10, aUpper <= 10 && Rand(1L) > aUpper)
+  setTest(2,
+    aUpper > bUpper && bUpper > 100 && Rand(1L) > aUpper,
+    bUpper > 100 && Rand(1L) > aUpper && aUpper > bUpper)
+
+  setTest(2, Rand(1L) > aUpper || aUpper <= 10, aUpper <= 10 || Rand(1L) > aUpper)
+  setTest(2,
+    aUpper > bUpper || aUpper <= Rand(1L) || aUpper <= 10,
+    aUpper <= Rand(1L) || aUpper <= 10 || aUpper > bUpper)
+
+  // Partial reorder case: we don't reorder non-deterministic expressions,
+  // but we can reorder sub-expressions in deterministic AND/OR expressions.
+  // There are two predicates:
+  //   (aUpper > bUpper || bUpper > 100) => we can reorder sub-expressions in it.
+  //   (aUpper === Rand(1L))
+  setTest(1,
+    (aUpper > bUpper || bUpper > 100) && aUpper === Rand(1L),
+    (bUpper > 100 || aUpper > bUpper) && aUpper === Rand(1L))
+
+  // There are three predicates:
+  //   (Rand(1L) > aUpper)
+  //   (aUpper <= Rand(1L) && aUpper > bUpper)
+  //   (aUpper > 10 && bUpper > 10) => we can reorder sub-expressions in it.
+  setTest(1,
+    Rand(1L) > aUpper || (aUpper <= Rand(1L) && aUpper > bUpper) || (aUpper > 10 && bUpper > 10),
+    Rand(1L) > aUpper || (aUpper <= Rand(1L) && aUpper > bUpper) || (bUpper > 10 && aUpper > 10))
+
+  // Same predicates as above, but a negative case when we reorder non-deterministic
+  // expression in (aUpper <= Rand(1L) && aUpper > bUpper).
+  setTest(2,
+    Rand(1L) > aUpper || (aUpper <= Rand(1L) && aUpper > bUpper) || (aUpper > 10 && bUpper > 10),
+    Rand(1L) > aUpper || (aUpper > bUpper && aUpper <= Rand(1L)) || (aUpper > 10 && bUpper > 10))
+
   test("add to / remove from set") {
     val initialSet = ExpressionSet(aUpper + 1 :: Nil)