Transcript for:
Organic Chemistry Key Concepts

hi everyone I hope you are doing well Everything goes well Uh today uh I want to go over uh review documents for review document for the test three exam as usual as we did until now Uh I hope it will be useful for you very informative and useful for you Uh consciously guys I send you review documents yesterday and I waited uh one day consciously because first of all I want you to push yourself to enforce yourself to solve the this problem uh first then you can compare uh this document Okay So let me start with the uh review documents starting with the first question Question number one why are ketones less reactive than aldahhides uh A Ketones are more stirly hindered B ketones are less electron deficient due to donation from two alkal groups C the statement is false Ketones are more reactive than aldahhides D both statements uh ketones are more cycllohender and ketones are less electron deficient due to donation from the two alkal groups The uh this section is correct This section covers everything uh in terms of the explanation of why aldahhides are more reactive than ketone Okay Yes the correct uh expression is that aldihides uh are more reactive than ketones Why because of uh two reasons Because of two reasons as we discuss more uh in this in the lectures Okay So yes imagine that aldahhide has this formula Just a second [Music] Aldahhide uh have this template RO oops hydrogen ketones have this template R CO another R these are can be same or different it doesn't matter I am talking about R group the smallest R group is the metal CH3 and Guys metal is 15 times larger than hydrogen Depending on the size uh depending on the mass okay we can say that uh metal group is much more larger than hydrogen uh the atomic mass of carbon is 12 plus 3 * 1 hydrogen's atomic mass is one so it should be 15 g hydrogen has 1 g of atomic mass okay so in real life guys remember our comparison uh when I say uh it's easy to show with the letters But in real life the reality is different guys Okay So our group imagine that we have a carbon with the size of 12 roughly and we have a metal group with the size of 15 We have a double bond Okay We have a oxygen with the size of 16 And we have a size we have a hydrogen with the size of one Okay this is the uh approximate representation of aldahhides What about ketones uh likewise we have a carbon with the size of 12 g roughly We have uh with the size of 12 This is the carbon And we have a size of material We have material with the size of uh 15 We have double bond oxygen with the size of 16 And we have another group It can be metal for example It can be metal ethyl propil I'm just talking about the smallest one Okay so you can compare with the largest ones Okay so I have one metal group So roughly guys we can show with this one this is carbon this is oxygen this is hydrogen this is hydrogen and this is metal Likewise this is carbon this is double bonded oxygen This is metal This is another metal Okay guys so a carbonial group carbonial groups are very reactive Oh sorry carbonial group in both functional group are very reactive So reactivity is associated with uh the opening of this uh carbon oxygen bonding Imagine that if this carbon oxygen bond is open generally I am talking about general reaction guys not 100% Okay So we can talk about partial positive charge on the central carbon carbonial carbon and partial negative charge on the oxygen Likewise we can talk about partial negative charge on the oxygen partial positive charge on carbon So reactivity is associated with the approaching ability of another react reactant to this carbon Imagine that we have a hydroxide We have a hydroxide and hydroxide means O Oxygen has 16 g of atomic mass Hydrogen is 17 So I am talking about O like a huge oxygen with a small hydrogen This is oxygen This is hydrogen Okay So this is O group guys uh uh with a excess electron on it Okay So for this oxygen it's easy to approach this carbon Why the steric effect of hydrogen is very very small Okay But I am talking about the same oxygen hydroxide excuse me This is oxygen This is hydrogen Now with the positive two excess electrons for this huge group it's very difficult to enter here it's very difficult to attack or bound this car you know what I mean that's why in the first case guys we can talk about easy uh easy easy reactivity And we can say alihide is much more reactive much more reactive because of the steric advantages Uh the st in this case we can talk about steric effect of hydrogen only But in this case let me show you with different color Let me show you with different color Okay So we can talk about steric effect of uh hydrogen in this case but we can talk about steric effect of metal group in this case That's why the first one aldahhides are uh more reactive More reactive is less stable Okay this is the first reason This is a stic effect What about the second reason electron electron or electronic effect Okay guys imagine that we know that from organic chemistry one metal groups metal groups metal or any other alkal groups are electron donating groups Okay metal or other alkal groups are electron donating groups So imagine that if you have if you have partial positive charge here if you have partial positive charge on the central carbon if you have a metal group guys metal groups metal groups stabilize this partial positive charge with by donating electrons By donating electrons Okay remember uh pay attention we have a carbonial center with the partial positive charge and we have a metal group it's electron donating group So the this metal group can stabilize the carbonial carbon positively charged carbon carbon by donating electron uh it's associated with stability But if you have two metal group or two alkal group I have one metal Can you see that I have one metal group over here the other metal group is over here I mean ketone And we have a partial positive charge over here If you have two metal group guys you can talk about more electron donation to do positive charge Imagine that there is a positive charge and if you donate if you send negative charge to positive charge you can stabilize you can stabilize this structure Okay So in ketones we have two electron donating group that stabilize more rather than aldahhide That's why guys this is electron effect The first one was static effect The second one is electron effect Because of these two effect because of these two effect ketones are cered and ketones are less electron deficient due to donation from two alkal groups Because of these two reason the correct answer is D Question number two if a compound is oxidized what's the result remember guys oxidation and reduction in organic chemistry I don't mean the meaning of the oxidation of reduction uh for other discipline electrochemistry in electrochemistry we can define different types of oxidation and reduction just remember definition of oxidation redu oxidation and reduction in organic chemistry So uh in case of oxidation we can talk about decreased carbon hydrogen bonding decreased So A is not correct B we can talk about larger or higher carbon hetroatom bonding That's why B is not correct C increased carbon hetroatom bond or decrease or fewer carbon hydrogen bond or increase double bond Yes guys all of this one the first one is increase carbon hetroatom the second one decrease carbon hydrogen bonding the third one increase double bond all of three satisfy the definition of oxidation that's why the correct answer is C uh the fever double bond no it should be larger double bond question number three what's are the position of n substitute in product of the following reaction remember guys I try to avoid to ask this kind of question generally so what's the product of this reaction it depends so many factor it sounds a little bit memorization but especially in organic chemistry too I have to ask this kind of questions sometimes Okay So uh and if so if I ask you this kind of question guy I can simplify as much as possible What does it mean i am talking about orto metapirection or or metap addition uh to the real uh molecule parent molecule Okay guys so it relates to addition reactions So remember what happens in case of or automeita and para addition uh remember electrofilic aromatic addition reactions uh before So if you have a metal connected benzene group known as tolian pay attention guys we have a metal group it's already connected before maybe before us okay it's metal group tolian uh tolian means metal connected benzene but remember guys tolian is orto and parad director orto means One two one two means one two one two direction uh uh one two addition okay let me show you with different color this is one two it means the second substitute can be connected to here or here these two positions are one two position 14 position means is this one If the first one is here the second one should be 1 2 3 4 Okay guys the upcoming uh substitute should be connected to this point nowhere else Okay So the upcoming uh the uh uh the next substitute is nitro How can we understand this one nitric acid in the presence of sulfuric acid it means nitro addition So also guys all answer consists of nitro addition Okay So we have to focus on orto or para addition In the first case guys in the first case I have metal group and nitro they are in the 14 position So it's correct In the second case I have metal group and nitro group Their position is one two or position It's correct What about this one i have metal group 1 2 3 and nitro group uh is on the 13 position One three position one three position means meter So a metal is not a meta director So this one is not correct So the correct answer should be D Okay If I provide you Matiel as a or para director most likely I can ask you the other famous uh directors maybe Nitro Nitro remember Nitro is a meta director not or para So please uh return back your notes and pay attention which one was or autotodirectionctor or uh paradirector which one was meta director Okay question number four What's the product of the following reaction yes this is exactly what I mean Uh I have a nitro group already connected before us before everything Okay the blue nitro pay attention guys the blue nitro is the first substitute Once it's connected it determines the following substitutes Make sense once once it's connected it uh navigates the following constitutions to the meta position one three position So in in this question blue nitro is the first substitute and red nitro should be second constitute substitute excuse me So uh the first one is one two position or position It's not correct The second one is nitro 1 2 3 meta position It's correct The third one is para position It's not correct So the correct answer should be two only Two only Okay So what types question number five what types of reduction occurs in the following reactions guys I am talking about carbon oxygen double bond and carbonarbon double bond Imagine a molecule including both carbon oxygen double bond and carbon carbon double bond Uh if you try to hydrogenize if you try to hydrogenize this molecule with the excess hydrogen gas I am talking about excess hydrogen gas Okay guys both double bond can be reduced because we have so many we have so many hydrogens We have so many hydrogens Okay But if you have one equivalent or one mole it doesn't matter Imagine that if you have a one mole of hydrogen gas only carbonarbon bond is reduced Okay because it's vulnerable for accepting hydrogen gas more Okay guys if I ask you excess electro excess hydrogen containing reaction uh reaction in the review most likely you can expect similar question in final exam uh test three that's why question number three yes all of all of the double bonds should be reduced question number six which statement below best describe the following reaction that okay guys I have uh remember on the left side I have one heteroatom only there is no multiple bond nothing else on the right side I have one multiple bond and one heteroatom so that's why we can talk about oxidation question number uh the correct answer is a question number seven give the name of for the following compounds Okay imagine that guys uh this kind this is a molecule with the aldahhide template Uh I want to show I want to show in detail Please follow me Let me print screen and take this one and put here Okay Yes guys Imagine uh I generally like working with the large um shape Oops This one Okay I can show guys And we have broine No broine is coming to us Okay So let me locate carbons I have one carbon over here the other carbon the other carbon the other carbon the other carbon So let's talk about the hidden hydrogens's We have one hydrogens's over here 1 2 3 4 1 2 3 4 Yes we have one hidden hydrogen But if the bromine uh is coming to us the hydrogen should be going away from us Okay So what about this one we have one hydrogen and we have three hydrogens over there Okay Yes So let's focus on the chyal carbon Kyle carbon we can show with the dark blue Okay we have a kyal carbon guys So first of all so first of all we have to uh uh we can name first then we can assign uh stereochemical purity or vice versa We can start with the naming first guys Guys remember let's talk about here one carbon two carbon three carbon We have to find the longest chain Okay so we can we can suppose that this chain is longest carbon chain 1 2 3 4 carbon It's associated with butane butane but it's aldahhide Why we have one hidden hydrogen So it's aldahhide So we can say butanal instead of butane So it's butanal So what kind of butanal we have uh we have one metal group over here We have one metal group over there and one bromine one bromine bromine and metal guys So we can we can assign the number first the carbon second carbon third carbon and fourth carbon So we have bromine and metal as a substitute Which one alphabetically come first bromine What's the number of bromine two So we can say we can say we can say uh two uh bromo what's the number of metal three metal Uh three metal we can say uh three metal two bromo three metal but okay so this part is okay bro metal so what about the uh stereochemical assignment So we have remember what we did in organic chemistry one this carbon is kyal carbon why it's connected to one two three and four different substitute okay since if if the carbon is connected to four different substitute this carbon should be ky k chyal carbon okay and it should be reaction center So we have to assign the a priority purity number depending on the size of the substitute Guys this number imagine that bromine I have carbon is connected to directly carbon is carbon is directly connected to uh bromine Come on And this carbon and this carbon and this hydrogen among them broine is largest So the first priority should be assigned to bromine My wonderful amazing incredible outstanding friends This numbering uh is totally different than this numbering These are not same These are different We can talk about two different types of numbering Okay This numbering depends on uh depends on the chain condition of the change depends on the uh existence or absence of the functional group I mean this kind this naming this numbering But this numbering depends on atomic size So the first priority should be given bromine The what the first uh the last priority should be uh given to hydrogen Definitely hydrogen is the smallest Okay What about the third one and the fourth one second one and the third one Sorry Okay guys we have to compare these two carbon We have to compare with this two carbon Okay So this carbon is connected to oxygen with double bond If you have a double bond it you can suppose that we can talk about uh in remember instead of one one uh carbon oxygen double bond you can talk about two carbon oxygen double uh single bond So you can talk about two oxygen So the second priority should be definitely given to this carbon because oxygen is larger than this carbons and the third priority should be given here Okay So uh and guys you shouldn't you have to you have to uh uh you have to adjust your location when you look at the molecule you shouldn't see hydrogen Okay so you have to you have to look this molecule from somewhere else or maybe here guys I have broine that's coming to me and uh second period is also here Third period is also here So pay attention to uh arrangement It should be 1 2 3 1 2 3 1 2 3 So I can talk about clockwise arc That's why remember in in case of clockwise arc orientation we can define r we can assign our uh stereo isomer to this molecule So what's the number of uh kyal carbon what's the number of kyroarbon this is the second carbon So we can say 2 r 2 r two broome metal butan This is the exact name of the molecule Okay This is the exact name of the molecule Yes correct answer is A Question number eight What's the name of the following compound guys uh I made a mistake here Thank you for those who warn me who notify me about my mistake Guys remember uh I can show like that First of all we have to find the template We have to find the parent longest carbon chain One carbon two carbons three carbons four carbons five and six So the chain the template or the chain the parent should be hexane hexane but we have caroxilic acid over here so we can say hexanoic acid Okay it's a kind of co excuse me co this is a template for carboic acid So it should be hexoninoic acid So what kind of hexoninoic acid we have so guys we have to start numbering from here because this is the center for functional group This is the carbon that's connected to functional group Remember naming if you have a functional group like caroxyic aldahhide or something like that you have to start numbering uh on this carbon Okay So this is the first one This is the first carbon This is second carbon This is third carbon This is fourth carbon This is fifth carbon And this is sixth carbon So we have three metal uh that's connected to back bond So these are our uh material groups 1 2 3 So what's the number of the metal groups 2 3 4 So 2 3 4 We have three metal groups We can that's why we can say three metal 2 3 4 3 metal hexonoic acid 2 3 4 3 metal hexonic acid Guys we have two correct answer Unfortunately it's my mistake You can ignore C You can ignore C I will let you know you can ignore C Uh so the correct answer should be B Okay So if you prepare much more questions sometime you can make such a minor mistake Okay Question number nine Which of the following is the uh least polar organic compound uh guys imagine we have a CO over here We have caroxilic acid We have carbonial and hydroxide group in the in D Polarity is associated with existence of polar group Okay So uh remember in this case guys we have carbon oxygen Sorry for my handwriting guys I can carry this part to the paint folder Don't worry about it I don't want to use uh mouse when I writing Okay guys so in this case we have this group In this case we have only hydroxide group In this case we have only carbon Um I can show clearly in this case we don't have any we don't have any polar group Okay So it's also a symmetrical molecule Can you see that it's symmetrical molecule That's why uh zero uh polarity for A What about the others guys d has two polar group one to D Okay And uh C has hydroxide group and B has carbonial group only But guys hydroxide group is much more polar than carbonial group because hydroxide group can make hydrogen bonding uh to talk about hydrogen bonding carbonial group is not enough guys We have to another molecu we have to have another molecule including free hydrogen So hydroxide group is much more electrogative than carbon So the polarity order should be like that Polarity order should be like that [Music] D uh should be most polar C and B and A So D is the most polar organic compound Okay D is the most polar organic compound A is the last B Question number 10 Which of the following amines are classified as a secondary amine in case of amine in case of amine please pay attention Remember what we discussed You have to focus on amine connected You have to focus on carbon that's directly connected to amine Okay that's directly connected to amine So remember in this case uh this amin is connected to one two carbon that's why this is secondary okay uh in the in this case this I mean I can show guys we have enough Okay So yes uh in the first case come on in the first case this amin is connected to one hydrogen the other hydrogen the carbon the carbon no need to show these hydrogens's Okay So this amin is connected to one R group One R group and two hydrogen So it's primary What about this am I mean let's talk about this I mean I have uh okay so focus on this amin This amine is connected to one R group and two hydrogen group So the second one is also primary What about the third one mhm I have am I mean in the middle uh carbon carbon carbon carbon carbon Okay So we can talk about one R group to another R group and hydrogen So we have two R groupoup that's connected to I mean that's why this is secondary Okay guys please pay attention Please pay attention I want to show a difference for you When you talk about Okay Uh if you talk about am amine or amine amine or am I mean it doesn't matter it's amine and hydroxide Uh guys please pay attention The first one is uh primary MI because in the case of nitrogen you have to focus on nitrogen you have to focus on carbons that's directly connected to nitrogen Okay you have to focus on carbon uh you have to focus on carbons that's directly connected to nitrogen But in case of hydroxide or any other types of uh primary secondary tertiary arrangement you have to focus on uh the carbon that's connected to oxygen You have to focus on this one Uh in the first scenario this is our attention center In the second case this is our attention center not oxygen Okay So when you look at this nitrogen when you focus on this nitrogen you can easily see we have one R group and two hydrogen So this are primary But when you look at here guys when you look at here you have to this this carbon is your attention center So this carbon is connected to two R group two R group That's why it's secondary The secondary alcohol is primary amine Nitrogen is exceptional Okay When you define the primary secondary tertiary nature of nitrogen containing compounds you have to you have to focus nitrogen directly But in case of alcohols you cannot focus this oxygen You have to focus on this carbon Okay So the correct answer should be C Question number 11 What's the common name of the following compounds it's a kind of amine What kind of amine secondary but amine Secondary but amine But as please pay attention it's uh it's secondary but secondary but is the name of the substitute Okay it does not mean that this amine is secondary amine Oh sorry guys We have one two three four carbon and Okay so this uh what's the name of this substitute it's but right bilain turns to bil I am talking about R group In case of amine the parent name should be amine because amine is a functional group It's a kind of group functional group So we have to end naming with amine So it's a kind of alkalam amine What kind of alkal we have butil What kind of butil secondary but why because it's connected to second carbo secondary amine Okay but this amine is not secondary amine The name of the molecule is secondary butil Okay please pay attention to this one Secondary but is just only substitute and amine is the parent Amine is the parent Be relax I never ask you such a confusing question Question number 12 Arrange the following compounds in order of decreasing boiling point Put on the compound with the highest boiling point first Remember polarity of hydroxide O bond is larger than NH bond Why oxygen is located to the right uh right side From left to right polarity increases in periodic table So the more polarity the more flexible free hydrogen that can easily make hydrogen bonding The more hydrogen bonding possibility the higher boiling melting points as we discussed so many times Okay So in this case guys we have NH bonding we have O bonding we have nothing in the second one In second one there is no free hydrogen guys There is no free hydrogen because there is no hydrogen is connected to oxygen That's why no hydrogen bonding possibility Stronger hydrogen bonding possibility weaker hydrogen bonding possibility So the ranking should be 312 312 Okay the correct answer is C Question number 13 Arrange the following amines in order of decreasing water solubility Putting the most soluble amine first Oh excuse me It's my mistake It should be uh most soluble amine It should be most soluble alcohol It's my mistake It should be most soluble alcohol first Okay guys Yes I am talking about solubility uh solubility in water is associated with existence of polar group first and the size of the non-polar group second If you have a larger nonpolar group you can decrease solubility in water First all of these molecule are soluble in water But we have to compare which one should be soluble more Just focus on the second one guys Uh let's talk about that This is the polar part This is the polar part and this is the polar part Polar parts are same in these three molecules But non-polar parts when you talk about the non-polar parts can you see that it consists of one two three four carbon it's a hydrocarbon with the length of four carbon in this case guys what how many carbon we have one two three it's a non-polar hydrocarbon with the size of three carbon and 1 2 3 4 5 6 It's a nonpolar chain uh non-polar hydrocarbon chain with the size of six carbon Okay since uh this molecule this molecule is smaller non-polar group that prevents solubility in water we can say the second molecule should be much more soluble Why because this molecule has smaller non-polar parts Non-polar parts prevent solubility in water But if you have smaller you can talk about solubility The second one should be more soluble as three carbon The first one should be secondly uh soluble and the third one should be less soluble or least soluble So the ranking should be 213 23 Okay question number 14 Which of the following correctly describe a peptide bond guys peptide don't forget peptide bond is a kind of amite bond We already talked about amino acids and proteins a couple of times but tomorrow we will go over chapter 27 Oh I excuse me sorry today we discussed we already finished uh amino acids and proteins chapter 27 So guys as you can easily remember from our session today uh peptide bond is a kind of amite bond between carbon and amine group Carbonial and amine group uh forms amide bonding Question number 15 is the correct answer should be C Question number 15 What's formed by the combination of three amino acids three amino acid means three peptide So in exam you can expect other options you know if you have four it should be tetrapeptide as we discussed today in detail Okay If you have a peptide change including amino acid including until for amino acid 40 we can say oligopeptide After 40 amino acid or beyond 40 amino acid we can say polyeptide Okay So critical threshold is 40 Oricopeptide are smaller than 40 amino acid and polyeptides are larger for amino acid Tripeptide means three amino acid Tetraeptite means four amino acid It's it's the simplest question of this review I think Anyway sometimes I can ask you simple question Question number 16 Which of the following compound is not amino acid guys the first requirement for amino acid is that is having caroxy group and amino group This is caroxy group Caroxyic acid group This is caroxyic acid group This is caroxyic acid group This is caroxilic acid group and the caroxilic acid are on the caroxilic carbon and in alpha carbon Alpha carbon is the carbon with a close proximity to the caroxile carbon Alpha carbon is h located adjacent to caroxil carbon So this is alphaarbon Alpha carbon Alphaarbon alpha carbon and alphaarbon and guys we have two requirement to talk about amino acid Uh we have we should have caroxy group on caroxyic acid carbon on the right side showing with the red color and the second requirement is having amine group on the alpha carbon So we have amine group on the alpha carbon So it satisfy amino acid definition We have amine group on this alpha carbon That's okay We have amine group on the alpha carbon That's okay But in this molecule guys please pay attention We don't have any amine group on alpha carbon So C is not amino acid C is something different We don't care But it's not amino acid Okay question number 17 What's the name of the following compounds uh guys in this case remember the roots Uh remember the original molecule is to don't forget So metal should not be included to naming Uh this is tolian very famous root Okay So uh since the substitute is connected to here we can we can start numbering from here Numbering from here and we can follow this way 1 2 3 4 5 6 or we can follow other way 1 2 3 4 5 six Okay guys definitely guys we have to follow blue numbering to assign lowest number possible to the substitute As a substitute we have what we have bromine and chlorine Bromine is connected to second carbon Chlorine is connected to fourth carbon Bromine and chlorine Which one alphabetically comes first bromine So we we have to say two bromo for chloroian Two bromo four chloro If you follow the pink numbering it should be guys 1 2 3 4 chloro and six bromo six bromo four chloroian 6 and4 It's definitely wrong because these are larger now We don't want it Correct answer is B Question number 18 What's the correct assignment of the name of the following substitute benzines guys this is an unfortunately you have to know you have to memorize Sometimes I rarely say I really say excuse me you have to memorize These are one of them This is an aminozene or am an anoline This is tolen metalbenzene or tolian Aminoenzene or aneline And also this is a styne guys Styin metilan group metane group not metane group That's why we have a specific name like styon Okay Styrron analine torian Okay The others does not satisfy the naming Question number 19 What's the correct structure for analine it's very similar guys Sometimes coincidentally very similar question can be followed each each other Okay So analine should be a second one Well correct selection for analine C So excuse me it's wrong Yeah this is the one of my wrong answer The correct structure for analin should be uh B not C It should be B Question number 20 What's theopactic name of the following compound it should be guys remember what I said what I said these are tolian it's not metal benzene we we have to say toen and also guys uh we can decide the position of nitro group uh the position of nitro group should be what one 2 3 one three position One position is me nitro The correct answer should be B Okay So this is the end of the review Okay guys Okay Yes Uh this is the end of the review guys I hope it was useful for you I strongly advise you watch a couple of times before taking exam In test three exam you can expect very similar question But be careful Some of them can be tricky Uh my you know you are familiar with my uh question style my teaching style In the real session real lectures we discuss much more complicated molecules or reactions not in exams uh I try to ask you simple straightforward question but they require attention Okay guys yes I want to stop uh recording now and I will deliver this video uh quickly maybe tonight So okay see you tomorrow Bye-bye