This is a video guide so video says more than text but i do my best to describe hard parts. Video contains all achievements you can get from single walkthrough. Time-related links you can find on the YouTube description page of every video.

06:14 - Submissive *Put the can in the trash*
There is to be a Defiant (Hit the trashcan cop with the can) but can is dropped down to trash from CP's face xD.
10:35 - Malcontent *Escape the apartment block raid*
This is a story-related achievement and cannot be missed.

0:47 - 3:50 - What cat? *Break the mini-teleporter in Kleiner's Lab.*
To get this achievement you must use teleport in Kleiner's Lab 10 times. You can also get this achievement later in Chapter 9a.
9:26 - Trusty Hardware *Get the crowbar.*
This is a story-related achievement and cannot be missed.
0:40 - Lambda Locator 1/45 *Find all lambda caches in Half-Life 2.*
During whole game you can see some hidden places with lambda letter on it. Check it out and get this achievement.

09:54 - Barnacle Bowling *Kill five barnacles with one explosive barrel.*
Description says all. Roll barrel, shot 2 times and wait.
31:53 - Anchor's Aweigh! *Get the airboat.*
This is a story-related achievement and cannot be missed.
01:27 - Lambda Locator 2/45
02:01 - Lambda Locator 3/45
06:51 - Lambda Locator 4/45
13:11 - Lambda Locator 5/45
22:01 - Lambda Locator 6/45
28:06 - Lambda Locator 7/45
28:25 - Lambda Locator 8/45 *Find all lambda caches in Half-Life 2.*
During whole game you can see some hidden places with lambda letter on it. Check it out and get this achievement.

Warning Lambda Locator #12 is changed from time this video has been recorded, Correct location showed below.
30:50 - Heavy Weapons *Get the airboat's mounted gun.*
This is a story-related achievement and cannot be missed.
38:48 - Revenge! *Destroy the Hunter-Chopper.*
This is a story-related achievement and cannot be missed.
40:54 - Vorticough *Discover the hidden singing vortigaunt cave.*
There is an open tube at just before the ending of chapter where you open water dum and just after you destroy Hunter-Chopper. It is full of radioactive waste so you better get some health before going through.
0:12 - Lambda Locator 9/45
0:33 - Lambda Locator 10/45
4:17 - Lambda Locator 11/45
13:55 - Lambda Locator 12/45 (Location is changed now)
Correct location on video below
15:14 - Lambda Locator 13/45
18:42 - Lambda Locator 14/45 (Different from the original game)
22:10 - Lambda Locator 14/45 (Original location. Not counting in Update)
24:19 - Lambda Locator 15/45
25:31 - Lambda Locator 16/45
25:57 - Lambda Locator 17/45
33:16 - Lambda Locator 18/45 *Find all lambda caches in Half-Life 2.*
During whole game you can see some hidden places with lambda letter on it. Check it out and get this achievement.

08:39 - Zero-Point Energy *Get the Gravity Gun in Black Mesa East.*
This is a story-related achievement and cannot be missed.
09:39 - Blast from the Past Find the HEV Suit Charger faceplate in Eli's scrapyard.
Just after you get Gravity Gun on top of the shelf you can find HEV Suit Charger.
11:55 - Two Points *Use Dog's ball to make a basket in the scrapyard.*
Just throw Dog's ball in a basket. That's not easy but you can try many times.
13:37 - Flushed *Kill an enemy with a toilet.*
There is a toilet in a scrapyard and there is to be a one headcrab later. I am failed to get it there but you can.
0:16 - Lambda Locator 19/45 *Find all lambda caches in Half-Life 2.*
During whole game you can see some hidden places with lambda letter on it. Check it out and get this achievement.

23:07 - Hallowed Ground *Escort Gregori safely through the church cemetery.*
This is a story-related achievement and cannot be missed.
0:00 - 26:11 - Zombie Chopper *Play through Ravenholm using only the Gravity Gun.*
During whole chapter you must use ONLY Gravity Gun. I am took Dog's ball with me, thats make walkthrough easy.
03:27 - Lambda Locator 20/45
07:14 - Lambda Locator 21/45
09:52 - Lambda Locator 22/45
26:18 - Lambda Locator 23/45 *Find all lambda caches in Half-Life 2.*
During whole game you can see some hidden places with lambda letter on it. Check it out and get this achievement.

08:49 - Where Cubbage Fears to Tread *Defend Little Odessa from the Gunship attack.*
This is a story-related achievement and cannot be missed.
14:40 - OSHA Violation *Kill 3 enemies using the crane.*
When you get to the crane there is to be the only 3 enemies below it. Use crane to kill all of them and get an achievement.
23:00 - Targeted Advertising *Pin a soldier to the billboard in the chapter Highway 17.*
When you get crossbow straight ahead of this point to be the billboard and a soldier on it. You know what you must to do ;-).
01:25 - Lambda Locator 24/45
03:28 - Lambda Locator 25/45
18:49 - Lambda Locator 26/45
25:09 - Lambda Locator 27/45
26:29 - Lambda Locator 28/45 *Find all lambda caches in Half-Life 2.*
During whole game you can see some hidden places with lambda letter on it. Check it out and get this achievement.
08:49 - One Man Army 1/6
17:50 - One Man Army 2/6
36:08 - One Man Army 3/6 *Destroy six gunships in Half-Life 2.*
During the game there is to be a 9 or 10 gunships, you can run or you can shoot in most cases.

11:10 - 16:03 - Keep Off the Sand! *Cross the antlion beach in chapter Sandtraps without touching the sand.*
Description says all. You must not step out to the sand while crossing beach. Use rocks and other stuff you can find, there are plenty of them.
23:34 - Bug Hunt 10/50
25:48 - Bug Hunt 20/50
26:47 - Bug Hunt 30/50
30:22 - Bug Hunt 40/50
31:14 - Bug Hunt *Use the Antlions to kill 50 enemies.*
Throw pheropods to the enemy and antlions kill them. You can do this during chapter 8 and 9 only.
09:12 - One Man Army 4/6
34:52- One Man Army 5/6
35:17 - One Man Army *Destroy six gunships in Half-Life 2.*
During the game there is to be a 9 or 10 gunships, you can run or you can shoot in most cases.
03:15 - Lambda Locator 29/45
13:53 - Lambda Locator 30/45 *Find all lambda caches in Half-Life 2.*
During whole game you can see some hidden places with lambda letter on it. Check it out and get this achievement.

0:24 - Flushed *Kill an enemy with a toilet.*
There is a toilet at one of the cells. Use them to kill a headcrab in another cell if you don't do this in chapter 5.
03:11 - Lambda Locator 31/45
08:56 - Lambda Locator 32/45
17:18 - Lambda Locator 33/45 *Find all lambda caches in Half-Life 2.*
During whole game you can see some hidden places with lambda letter on it. Check it out and get this achievement.
12:09 - Hack Attack! 1/5 *Kill five enemies with a Manhack.*
Use gravity gun to capture manhack and throw it to the enemy. During whole game there is to be a lot of places with manhacks and soldiers. Starting from this chapter and to the chapter 12. The most counts of manhacks is to be at chapter 10.

23:54 - Warden Freeman *Survive the second turret standoff in Nova Prospekt.*
This is a story-related achievement and cannot be missed.
05:43 - Lambda Locator 34/45 *Find all lambda caches in Half-Life 2.*
During whole game you can see some hidden places with lambda letter on it. Check it out and get this achievement.
21:26 - Hack Attack! 2/5
21:48 - Hack Attack! 3/5
22:13 - Hack Attack! 4/5
22:38 - Hack Attack! *Kill five enemies with a Manhack.*
Use gravity gun to capture manhack and throw it to the enemy. During whole game there is to be a lot of places with manhacks and soldiers. Starting from chapter 9 and to the chapter 12. The most counts of manhacks is to be at chapter 10.

03:35 - Follow Freeman *Gain command of a squad of rebels in the uprising.*
This is a story-related achievement and cannot be missed.
22:59 - Radiation Levels Detected *Get through the toxic tunnel under City 17 in Half-Life 2.*
This is a story-related achievement and cannot be missed.
39:52 - Plaza Defender *Survive the generator plaza standoff in chapter Anticitizen One.*
This is a story-related achievement and cannot be missed.
00:28 - Lambda Locator 35/45
08:12 - Lambda Locator 36/45
16:01 - Lambda Locator 37/45
19:14 - Lambda Locator 38/45
28:56 - Lambda Locator 39/45
31:59 - Lambda Locator 40/45
43:23 - Lambda Locator 41/45
45:56 - Lambda Locator 42/45
46:18 - Lambda Locator 43/45
51:15 - Lambda Locator 44/45 *Find all lambda caches in Half-Life 2.*
During whole game you can see some hidden places with lambda letter on it. Check it out and get this achievement.

04:43 - Counter-Sniper *Kill all of the snipers in City 17.*
There is to be a 5 of them before you save Barney. Use grenades or rocket launcher if you have it.
19:41 - Fight the Power *Shut down the supression device by disabling its generators.*
This is a story-related achievement and cannot be missed.
33:33 - Lambda Locator *Find all lambda caches in Half-Life 2.*
During whole game you can see some hidden places with lambda letter on it. Check it out and get this achievement. This is a final location.
42:25 - Giant Killer *Survive the rooftop strider battle in the ruins of City 17.*
This is a story-related achievement and cannot be missed.

07:48 - Atomizer 5/15
09:02 - Atomizer 10/15
10:01 - Atomizer *Disintegrate 15 soldiers by throwing them into a Combine ball field.*
Throw soldiers or their dead bodies to the white glowing fields.

10:43 - Singularity Collapse *Destroy the Citadel's reactore core.*
This is a story-related achievement and cannot be missed.