diff --git a/Lib/test/test_grammar.py b/Lib/test/test_grammar.py
index 9d473770f3b20b..2b9f7df0bd25d1 100644
--- a/Lib/test/test_grammar.py
+++ b/Lib/test/test_grammar.py
@@ -214,99 +214,35 @@ def test_bad_numerical_literals(self):
         check("1e+", "invalid decimal literal")
 
     def test_end_of_numerical_literals(self):
-        def check(test):
-            with self.assertWarns(DeprecationWarning):
-                compile(test, "<testcase>", "eval")
-
-        def check_error(test):
-            with warnings.catch_warnings(record=True) as w:
-                with self.assertRaises(SyntaxError):
-                    compile(test, "<testcase>", "eval")
-            self.assertEqual(w,  [])
-
-        check_error("0xfand x")
-        check("0o7and x")
-        check("0b1and x")
-        check("9and x")
-        check("0and x")
-        check("1.and x")
-        check("1e3and x")
-        check("1jand x")
-
-        check("0xfor x")
-        check("0o7or x")
-        check("0b1or x")
-        check("9or x")
-        check_error("0or x")
-        check("1.or x")
-        check("1e3or x")
-        check("1jor x")
-
-        check("0xfin x")
-        check("0o7in x")
-        check("0b1in x")
-        check("9in x")
-        check("0in x")
-        check("1.in x")
-        check("1e3in x")
-        check("1jin x")
-
-        check("0xfnot in x")
-        check("0o7not in x")
-        check("0b1not in x")
-        check("9not in x")
-        check("0not in x")
-        check("1.not in x")
-        check("1e3not in x")
-        check("1jnot in x")
-
-        with warnings.catch_warnings():
-            warnings.simplefilter('ignore', SyntaxWarning)
-            check("0xfis x")
-            check("0o7is x")
-            check("0b1is x")
-            check("9is x")
-            check("0is x")
-            check("1.is x")
-            check("1e3is x")
-            check("1jis x")
-
-        check("0xfif x else y")
-        check("0o7if x else y")
-        check("0b1if x else y")
-        check("9if x else y")
-        check("0if x else y")
-        check("1.if x else y")
-        check("1e3if x else y")
-        check("1jif x else y")
-
-        check_error("x if 0xfelse y")
-        check("x if 0o7else y")
-        check("x if 0b1else y")
-        check("x if 9else y")
-        check("x if 0else y")
-        check("x if 1.else y")
-        check("x if 1e3else y")
-        check("x if 1jelse y")
+        def check(test, error=False):
+            with self.subTest(expr=test):
+                if error:
+                    with warnings.catch_warnings(record=True) as w:
+                        with self.assertRaises(SyntaxError):
+                            compile(test, "<testcase>", "eval")
+                    self.assertEqual(w,  [])
+                else:
+                    with self.assertWarns(DeprecationWarning):
+                        compile(test, "<testcase>", "eval")
+
+        for num in "0xf", "0o7", "0b1", "9", "0", "1.", "1e3", "1j":
+            compile(num, "<testcase>", "eval")
+            check(f"{num}and x", error=(num == "0xf"))
+            check(f"{num}or x", error=(num == "0"))
+            check(f"{num}in x")
+            check(f"{num}not in x")
+            with warnings.catch_warnings():
+                warnings.filterwarnings('ignore', '"is" with a literal',
+                                        SyntaxWarning)
+                check(f"{num}is x")
+            check(f"{num}if x else y")
+            check(f"x if {num}else y", error=(num == "0xf"))
+            check(f"[{num}for x in ()]")
+            check(f"{num}spam", error=True)
 
         check("[0x1ffor x in ()]")
         check("[0x1for x in ()]")
         check("[0xfor x in ()]")
-        check("[0o7for x in ()]")
-        check("[0b1for x in ()]")
-        check("[9for x in ()]")
-        check("[1.for x in ()]")
-        check("[1e3for x in ()]")
-        check("[1jfor x in ()]")
-
-        check_error("0xfspam")
-        check_error("0o7spam")
-        check_error("0b1spam")
-        check_error("9spam")
-        check_error("0spam")
-        check_error("1.spam")
-        check_error("1e3spam")
-        check_error("1jspam")
 
     def test_string_literals(self):
         x = ''; y = ""; self.assertTrue(len(x) == 0 and x == y)