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 It is customary to learn/review the halachos of berachos recited over many different types of fruits
since we will have an opportunity to savor these fruits on Tu B'Shvat, and we want to avoid making a beracha in vain.
A. BERACHA RISHONA FOR FRUIT
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The beracha rishona for a fruit is either a 'Boray Pri Ha-Etz', or a 'Boray Pri Ha-Adamah'
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Sometimes fruits require a beracha to be said over them and other times not.
B. FRUITS NOT REQUIRING A BERACHA, [2]
1. Foods which are primarily eaten as part of a meal (that requires washing for bread) are exempted by the Brocha HaMotzi made on the bread. These foods do not require their specific brocha rishona, nor do they require their brocha achrona, as they are covered by Bircas HaMazon.
2. Although fruit and other dessert-type foods usually do require a separate brocha, (see Section C. below) if they are eaten as an integral part of the meal, they do not require a separate brocha. For example:
a) Fruit eaten as the ONLY main course
A Meal may consist only of bread, a fruit platter, beverage
and dessert, in which case the MAIN course is the fruit platter.
Some Rishonim rule that a separate brocha is required, however, if
one starts eating the fruit with bread, he is not required to make
a separate brocha.
b) Fruit Eaten as One of the courses
In this case, fruit is not considered a meal type food and requires
its own brocha UNLESS it is eaten TOGETHER with bread.
A dispute among Poskim is the quantity of fruit that needs to be
eaten with bread to be exempted by the Bircas HaMotzi. Most Poskim
rule that it is enough to start eating the fruit with bread and to
finish eating the fruit with bread even though one does not intend
to consume all the fruit with bread.
Another opinion is that each bite of fruit must be eaten together
with bread. The Poskim advise that one should first make the
brocha on fruit and eat some of the fruit without bread.
Afterwards, one may continue to eat the fruit with or without
bread.
[ In some Machzorim (e.g. Artscroll) a 'Boray PriHaetz' for eating
an apple after eating bread is included, while others
(e.g. NCSY bencher) have the 'Boray PriHaetz' for apple
immediately after kiddush, before washing for bread. ]
c) Fruit Eaten for Dessert Entirely with Bread
If fruit is not eaten for satiation, but as a dessert, it is not
exempted by the Brocha Hamotzi UNLESS it is eaten entirely with
bread, because it becomes tofel (subordinate) to the bread.
d) Fruit Prepared for use in a meal
Fruit cooked into a dish which is commonly served as a meal-type
food e.g. Pineapple Chicken, does not require a separate brocha.
But fruits cooked for use as a dessert, e.g. stewed plums, require
a brocha.
e) Appetizers
Many Poskim rule that fruit eaten as an appetizer is considered a
meal-type food and does not require a separate brocha.
Some Poskim rule otherwise and the minhag haolom (general custom)
is not to make a brocha on items which are definitely eaten as
appetizers. Alternatively, like in b) above, the Poskim recommend
making a brocha for the fruit before washing for bread, with
intention to cover the fruit eaten during the meal. The size of
the fruit should be less than a k'zayis to avoid complications
with regard to the brocha achrona.
f) Fruit Eaten as a Tofel to a Meal-type food
When a dessert-type food, e.g. applesauce, is eaten as a tofel
(subordinate) to a meal- type food, e.g. potato latkes, it is
exempt from a brocha.
C. FRUITS REQUIRING A BERACHA, [2]
1. Fruit requires its own specific brocha (Boray Pri Haetz or Boray Pri Ha'Adamah), if it is eaten
a) at the end of a meal (that requires washing for bread) as a dessert, OR
b) as one of the courses of a meal eaten separately from bread, OR
c) as a snack between courses
2. Fruit eaten as dessert that are raw, cooked, baked, canned, dried or processed, requires a brocha.
D. ORDER OF FRUITS WHICH HAVE THE SAME BERACHA
1. [3] uses the following guidelines:
a) You say the beracha over the fruit you like BEST and find most
appealing.
b) If you like all of them equally, and there is among them one
of the 7 Species*, say Boray Pri HaEtz over that one, even if it
is not whole, while the others are whole.
For e.g., a sliced date takes precedence over a whole plum.
* The derivation of the 7 species (Shivas HaMinim) is from the Torah:
[1] "A land of wheat and barley, of vines, figs, and pomegranates,
a land of olives and honey." (Devarim 8:8) The principle is that
the closer the fruit is to the word 'land', the more preferred it is.
In the first phrase, VINES (GRAPES) are mentioned 3rd (after the
world 'land'), FIGS are 4th and pomegranates are 5th. In the second
phrase, OLIVES are mentioned 1st and HONEY (from DATES) are
mentioned 2nd. Thus, the ordering is OLIVES, DATES, GRAPES, FIGS,
POMEGRANATES.
c) If the fruits are outside the 7 species and only one of them
is WHOLE, say the beracha on the WHOLE one.
[ Question: What if they are all WHOLE or none is WHOLE?
Rabbi Aaron Tendler of Yeshivas Ner Israel, Baltimore said to pick whichever fruit one wants at the moment.]
A free course is available on ChinuchOnline.com with the above halachos and questions in a Lesson format, to test your understanding on these halachos, with various flow charts as learning aids.
Works from the following books are referenced:
[1] The Book of Our Heritage by Eliyahu Kitov
[2] Halachos of Berachos by Rabbi Yisrael Pinchas Bodner
[3] The Kitzur Shulchan Aruch by Rabbi Avrohom Davis
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Halachos/Laws 
