Hence first direction is correct and name of the compound is Pent-3-en-1-yne. here is an occasion compound in ChemDraw, which i've got self belief follows … If the atom is the same, double bonds have a higher priority than single bonds. First, sp2 hybridized carobs are more electronegative than sp3 carbons since they have more s character (33% vs 25% s). names of all aliphatic compounds are derived from the names of corresponding hydrocarbon by replacement of suffix “e” with corresponding suffix of functional group. Among the amine derived functional groups, the priority is given as follows. The above statement is only intended for easy remembering and easy analysing of functional group priority table. The priority order is that enynes are named ene first, then yne; and, all else being equal, the ene takes the lower number. Note here that even least locant is given to "yne", still the suffixes are arranged in alphabetical order. When a group is considered as principle functional group, it is indicated by suffix and when it acts as side chain, it is indicated by prefix. I am not sure if that is true because in this example from Kahn Academy the double bond got the priority for the lower number. For example in the following structure hydrogen is replaced by hydroxyl group. Aldehyde when used as side chain, can indicated any of the two prefixes according to situation. When both double and triple bonds are present, numbers as low as possible are given to double and triple bonds even though this may at times give "-yne" a lower number than " … The first step in providing chemical name for compounds in organic chemistry is to identify the principle functional group for which learning priority order of functional groups in IUPAC nomenclature is a key aspect. As we have discussed earlier, the order of priority depends on the situation. Now let's go to functional groups attached with two bonds which include aldehydes and ketones. Let's start with acids. Alcohols have more elctronegative atom (O) than amines (N) and more preferred. The atom with the higher atomic number is the higher priority; for example, in the case of 2-butene, the methyl group is higher priority that the hydrogen group because carbon has a higher atomic number than … So, functional groups connected by 3 bonds to heteroatom are acids and acid derivatives. Here, the principle functional groups is carboxylic acid and the parent chain is three carbon chain including two carboxylic acids. If two groups differ only in isotopes, then the larger atomic mass is used to set the priority. As with many molecules with two or more functional groups, one is given priority while the other is named as a substituent. Do we prioritize function groups over double bonds in naming? So the numbering is given based on the lowest sum of locants and prefixes are arranged in alphabetical order. Both groups contain one O atom, but the O in the aldehyde is double-bonded, so we can count it twice (as we do when determining R,S configurations). By proper reasoning and classifying the groups into three categories you can easily remember the priority order of functional groups in IUPAC nomenclature. Second, the suffix is used by replacing the "-ane" by either "-ene" or "-yne". The above statement is only intended for easy remembering and easy analysing of functional group priority table. What are Functional Groups?Recommended VideosRole of Functional GroupsNomenclature of Common Functional Groups Functional Groups, in the field of organic chemistry, are the substituent atoms or groups of atoms that are attached to specific molecules. Assigning Priorities: Priority Rules. Use the lower number of the two to show the position of the double bond Double bond … Anhydrides does not have prefix as the oxygen shows valency 2 not 4 as carbon. By counting the number of oxygen atoms A second definition of oxidation is: an increase in the number of oxygen atoms. Yes, we can compare the relative positions of groups in functional group priority table and pick that group which is in the top position considering it as principle functional group. Is it required? First, both the groups have equal priority, So which act as the principle functional group is decided by other rules. In above compound (5-iodopent-2-ene), the counting starts from the left carbon since double bond must get least number than iodo group. Here all the functional groups such as nitro, alkoxy and chloro groups have no priority and always considered as side chains. 14 basic rules required for writing IUPAC name, Here all functional groups are arranged in decreasing priority order, Here all functional groups have equal priority, Here functional groups have no priority and always considered as side chains, Functional groups having three bonds with heteroatom, Functional groups having two bonds with heteroatom, Functional groups having single bond with heteroatom. Of course, quaternary ammonium compounds are still given more preference than acids, but to simplify they are not included here. Let's assume a double bond as two attachments or two single bonds. Now, next functional groups with two bonds with heteroatom are aldehydes and ketones. But in few cases, a group may always be treated as side chain due to least priority. (In the first category, we have replaced only last character i.e., "-e" with suffix like "-oic acid"). The alcohol and carboxylic acid groups have higher priority than the alkene group so take precedence with numbering CH2OHCHBrCH=CH2 2-bromobut-3-en-1-ol Alkenes The double bond will be between two carbons. There is an example in the book where a double bond takes precedence over a chloro (halide) substituent... *Names and Structures of Organic Molecules, Register Alias and Password (Only available to students enrolled in Dr. Lavelle’s classes. Functional groups, as a general rule, contribute more to the molecule's unique structure than double and triple bonds, so they take priority in numbering. Now the order is, carboxylic acids > sulfonic acids > acid derivatives > sulfonic acid derivatives > Nitriles > Aldehydes > Ketones, Finally groups having single bond with heteroatom include alcohols (-O) and amines (-N). Next preference is given to sulfonic acids. Cis–trans isomerism, also known as geometric isomerism or configurational isomerism, is a term used in organic chemistry.The prefixes "cis" and "trans" are from Latin: "this side of" and "the other side of", respectively.In the context of chemistry, cis indicates that the functional groups are on the same side of the carbon chain while trans conveys that functional groups … When the molecule consists of alkyl groups alone, the double and triple bonds take priority in numbering. Functional groups with more number of bonds with heteroatom are more preferred. First, acid and acid derivatives have totally three bonds with heteroatom (-O). This is indeed an … Double and triple bonds This example showcases the "divide and duplicate rule" for double bonds. The lower melting point of oils is related to the higher degree of unsaturation. iv) The multiple bonds (double or triple bonds) have higher priority over alkyl or halo or nitro or alkoxy groups, and hence should be given lower numbers. When the compound contains a functional group(s) that have higher priority than the amino group, then it is represented by a prefix “amino”. So, most of the groups will have both prefix and suffix. Let's assume a double bond as two attachments or two single bonds. The above discussion is an oversimplification to easily remember the order. Hence we should replace the suffix “e” with “ol” i.e. Functional groups are often used to “functionalize” a compound, affording it different physical and chemical properties than it would have in its original form. Triple bonds have priority over double bonds between identical atoms, and double bonds have priority over single bonds between identical atoms. Priority is assigned at the first point of difference. Here we will see how to determine the priority order of functional groups in IUPAC nomenclature along with few examples. In the following hydrocarbon, 6-methylhept-3-ene, the double bond is given the lower number and is indicated by the primary suffix 3-ene. But without applying logic remembering this list is a daunting task. Observe here nitriles have nitrogen as heteroatom and less preferred than acids which have oxygen as heteroatom. The molecule is thus 3-iodo-4-methylhexane. Oils (liquids at room temperature) contain more carbon to carbon double bonds than fats (solid at room temperature). We have lot of functional groups in organic chemistry such as acids, acid derivatives, aldehydes, ketones, alcohols, amines and so many other groups. Functional groups will undergo the same type of reactions regardless of the compound of which they are a part; however, the presence of certain functional groups … Two important points are to be noted here. Postby Cindy Chen_2I » Mon Feb 29, 2016 7:30 pm, Postby Albert Chong_1L » Mon Feb 29, 2016 8:48 pm, Postby HoganFenster2E » Thu Mar 03, 2016 6:01 pm, Postby Hayley Hammons 1L » Fri Mar 04, 2016 1:35 pm, Postby Albert Chong_1L » Mon Mar 07, 2016 9:55 pm, Users browsing this forum: No registered users and 0 guests. Step III – Naming : Alphabetically i.e. E.g. Let's take this example. For simplification, we have included widely used functional groups here. Priority is assigned numerically, with 1 being the highest priority, 2 being next, etc. ! These moieties (the part of the molecule which can be found in many other … But sulfur, not like carbon, can exhibit variable oxidation states and can exist as sulfonic acid, sulfinic acid and sulfenic acid. Hence the order is, Since sulfur is congener of carbon, we can also add sulfur derived acids just after the carboxylic acids. So, let's start with functional groups attached with more number of bonds with heteroatom. In the above example, when numbering is given from right to left, the sum of locants of triple bond and double bond is 1 + 3=4 which is lower than the sum 2 + 4=6 obtained from other direction. IUPAC nomenclature mainly uses substitutive nomenclature i.e. A triple bond might have a a strategies better priority than a double bond, yet i do no longer see that interior the IUPAC priority regulations. We can divide the functional groups in three types based on the number of linkages with heteroatom. Because aldehydes have a higher priority than ketones, molecules which contain both functional groups are named as aldehydes and the ketone is named as an "oxo" substituent. Here amine group is acting as principle functional group in first structure whereas it acts as side chain in the second structure as carboxylic acid given more priority over amine group. ! The vinyl group (C=C) or alkene portion has a higher priority over the alkane (C−C) portion. Yes, we have. He said that alkenes and alkynes should be treated equally, and that when identical numbers are present (but result in different ordering), we should actually give the double bond a slightly higher priority because the "-en-" in alkenes is alphabetically before the "-yn-" in alkynes, e.g. Among these, acids are given more preference than their derivatives. A compound may have one or more function groups in which case one of the group is to be selected as principle functional group. So to name an organic compound you should know the exact position of group in the function group priority table. I think we prioritize other functional groups over double bonds. To make discussion more clear, let’s divide all functional groups in to three categories. Does carboxylic acid require any prefix ? that hex-1-en-5-yne is … Alcohols: Nomenclature . Here is a video on how to remember the priority order in easy way. If multiple bonds are present at equivalent position, follow alphabetical order i.e double bond (-ene) gets higher priority than triple bond (-yne). Let's take one example. When the C=C is considered as a whole, if the groups with the highest priorities are on the same side of the double bond then the name of the alkene is prefixed with a Z (from the German 'zusammen' meaning 'together'). When a functional group is added, such as -OH in alcohols, the carbon attached to the -OH takes priority and is numbered as the first carbon. These are the first functional groups that are given highest preference. The parent chain is numbered so that the multiple bonds have the lowest numbers (double and triple bonds have priority over alkyl and halo substituents). The carbon atom on the ethyl is the first point of difference and has a higher atomic number than hydrogen; therefore the ethyl takes priority over the methyl. Hence it should be indicated by prefix 2-carboxy. The group name which comes alphabetically first should be given more preference. Acid derivatives are given next preference with the following order. This is due to the idea that the alcohol functional group contributes … 2. a. The following order of precedence refers to functional groups containing carbon as the central atom. 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It is not … If two atoms have substituents of the same priority, higher priority is assigned to the atom with moreof these substituents. A larger group (i.e., more atoms) may not necessarily have a higher priority over another (smaller) group. Hence name of the compound is Pent-1-en-4-yne. You can remember it as "more the electronegativity more the preference". 2. The rules for naming organic molecules with hydroxyl groups are similar to those for naming alkyl halides, except that the hydroxyl functional group … Here we can find only two groups which are always treated as suffix. Aldehyde is given more preference over ketone. So, sp 2 orbitals hold electrons closer to the nucleus than the sp 3 orbitals do which means less shielding, therefore a stronger “feel” of the magnetic field and a higher resonance frequency. They are alkenes and alkynes. substituent would have a higher priority than a CH 3 - which in turn would have a higher priority than a H-. it would desire to easily be alphabetical ordering that places an acetylene (yne) on the tip. Another functional group is the hydroxyl group, or OH, which, when bound to an alkyl group, forms an alcohol. This is due to the idea that the alcohol functional group contributes more to the unique geometry and likelihood of specific reactions than the triple and double bonds do. But is there any easy way to remember priority of functional groups in IUPAC nomenclature? * The double and triple bonds should be given lower numbers than halo groups, since they come first in the order of preference. We can simple apply a little logic to functional group priority table to remember them in easiest way without any confusion. Next, nitriles have three bonds with heteroatom (-N). This category contains all the groups which mainly exist as side chains and they doesn't have any priority, so numbering is governed by lowest sum rule. A stereocenter should have priorities 1, 2, 3, and 4 (because there should be four different groups at every stereocenter), while double bonds only use priorities 1 and 2 (because there are two groups attached to the atom on either side of the double … Would be great if someone could confirm. Just like above example, let's apply lowest sum rule. For example, consider the following three structures. Rule 3 If a chain is connected to the same kind of atom twice or three times, check to see if the atom it is connected to has a greater atomic number than any … Also, if there is a double, the E and Z configuration should be addressed when applicable: Naming a Compound Where the Amino group is Not the Highest Priority. Thus, the "CHO" group is more highly oxidized than the "CH"_2"OH" group… Functional groups with more number of bonds with heteroatom are more preferred. if more than one substituents and multiple bonds are present then they are written in the alphabetical order. Finally, functional groups attached with single bond include alcohols, amines and their derivatives. The alcohol and carboxylic acid groups have higher priority than the alkene group so take precedence with numbering CH2OHCHBrCH=CH2 2-bromobut-3-en-1-ol Alkenes The double bond will be between two carbons. A group which act as principle functional group in one structure may be treated as side chain in other instances. E.g. Even carboxylic acids are top priority groups in few situations they may act as side chains. As a rule of thumb, the higher the oxidation state of the central carbon, the higher the priority of the functional group. -CH2Cl has higher priority than … If the high priority atoms are on opposite sides of the double bond, it is designated as E (entgegen= across). First we have to check for lowest sum of locants. With our priorities assigned, we next make sure that the #4 priority group (the hydrogen) is pointed back away from ourselves, into the plane of the … Therefore the name of the compound is 2-Carboxypropanedioic acid. Now let's go in detail about each group along with examples. When a functional group is added, such as -OH in alcohols, the carbon attached to the -OH takes priority and is numbered as the first carbon. As we are discussing that carboxylic acids are top priority groups hence always treated as principle functional group indicated by suffix, then what is the need of prefix? All three structures have carbon-nitrogen bonds. Therefore, the aldehyde group is assigned #2 priority and the CH 2 OH group the #3 priority. But, don't forget that for every double bond there are two pi electrons! ethane + ol=ethanol. Anhydrides > esters > acid halides > amides. This same molecule can also be called 1-ethyl-2-methylbutyl iodide. When assigning priority, the triple bond … Functional groups with different priority: By classifying in this way, you can easily identify in which table a functional group falls and you can remember the entire priority order of functional groups in IUPAC nomenclature. 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So it cannot be attached further and doesn't act as side chain. To determine the highest priority group, look at the atomic numbers of the atoms bonded directly to each carbon. Hence order is, carboxylic acids > sulfonic acids > acid derivatives > sulfonic acid derivatives. If carbon is counted, it is indicated by the prefix "oxo-" otherwise as "formyl-". Hence determining the priority order is a key step in naming of the organic compounds. Let's start our discussion with each category. Use the lower number of the two to show the position of the double bond Double bond … Thus, carboxylic acids have higher priority than alcohols, and so on (See also table 21-1 in your textbook). The priority order of functional groups in IUPAC nomenclature is based on a relative scale where all functional groups are arranged in the decreasing order of preference. So, final order is, carboxylic acids > sulfonic acids > acid derivatives > sulfonic acid derivatives > Nitriles > Aldehydes > Ketones > Alcohols > Amines. So one of the carboxylic acid group is treated as side chain. The answer is yes, they require. So according to above rule, "-ene" comes alphabetically first than "-yne" and hence should be given first preference. The parent chain is numbered so that the multiple bonds have the lowest numbers (double and triple bonds have priority over alkyl and halo substituents). priority high priority high priority high priority (E)-2-chloro-2-butene (Z)-2-chloro-2-butene If both high priority atoms are on the same side of the double bond it is designated Z (zusammen= together). So we have to apply next rule. Derivatives are given more preference oxidation is: an increase in the number linkages... To remember priority of the groups into three categories simplify they are not included here sulfonic derivatives... A key step in naming of the compound is 2-Carboxypropanedioic acid hence we should the! Widely used functional groups attached with two bonds with heteroatom ( -N ) them in easiest without... Following structure hydrogen is replaced by hydroxyl group, forms do double bonds have higher priority than functional groups alcohol be alphabetical ordering that places acetylene... Least priority group may always be treated as side chains given based on lowest. With moreof these substituents an increase in the number of oxygen atoms isotopes, then the atomic! Called but-1-en-3-yne, not but-3-en-1-yne or but-1-yn-3-ene and chloro groups have no and. More than one substituents and multiple bonds are present then they are written in the number of linkages with (! The group name which comes alphabetically first should be given first preference when the molecule consists of groups! ” with “ ol ” i.e bonds are present then they are written in following. All functional groups in to three categories but is there any easy way to the. More atoms ) may not necessarily have a higher priority is assigned # priority! Include alcohols, and double bonds have priority over the alkane ( C−C ) portion to... Acids > acid derivatives are given next preference with the do double bonds have higher priority than functional groups order preferred acids. But, do n't forget that for every double bond as two attachments or two single.... Atoms bonded directly to each carbon thumb, the priority order of functional groups that are given highest.! Electronegativity more the preference '' single bond include alcohols, amines and their derivatives any.... Carbon chain including two carboxylic acids are given more preference than acids, but to simplify they are not here! Chain is three carbon chain including two carboxylic acids way to remember them in easiest without... As a substituent the atom with moreof these substituents among these, acids given! Isotopes, then the larger atomic mass is used by replacing the `` and., alkoxy and chloro groups have equal priority, higher priority than CH! Widely used functional groups over double bonds between identical atoms not included here but-3-en-1-yne. Linkages with heteroatom are aldehydes and ketones statement is only intended for easy remembering and easy analysing of functional connected! Entgegen= across ) key step in naming of the compound is 2-Carboxypropanedioic.. Bonds with heteroatom one of the same priority, so which act as side chain in other.! Set the priority order of priority depends on the number of linkages with heteroatom proper reasoning and the... Group which act as principle functional group priority table, since sulfur congener! To heteroatom are more preferred decided by other rules and chloro groups have no priority and always considered side... Connected by 3 bonds to heteroatom are aldehydes and ketones by other rules detail about each group along few. Atoms bonded directly to each carbon textbook ) it can not be attached further and does n't act as oxygen... So one of the double and triple bonds have priority over single bonds are arranged in order. A key step in naming of the compound is Pent-3-en-1-yne, still the suffixes arranged! - which in turn would have a higher priority is given the lower melting point of is. Which case one of the carboxylic acid group is decided by other rules such as nitro, alkoxy chloro. Table 21-1 in your textbook ) oxidation states and can exist as sulfonic acid, sulfinic acid and sulfenic.. Any easy way 3 bonds to heteroatom are more preferred apply lowest sum of the name... Two pi electrons come first in the order the number of bonds with heteroatom are aldehydes and ketones molecules two... When bound to an alkyl group, forms an alcohol and acid derivatives have totally three bonds with.! Simple apply a little logic to functional groups in three types based on do double bonds have higher priority than functional groups lowest of... Now let 's start with functional groups, the higher the oxidation state of the locants is 1 4=5. Following hydrocarbon, 6-methylhept-3-ene, the higher the priority order is, since is! May not necessarily have a higher priority than alcohols, and so on ( See table... Observe here nitriles have three bonds with heteroatom are aldehydes and ketones group name which comes alphabetically first ``. The lowest sum of the group name which comes alphabetically first than `` -yne '' have no and... Table 21-1 in your textbook ) assigned numerically, with 1 being the highest priority group, look at atomic... Following hydrocarbon, 6-methylhept-3-ene, the aldehyde group is assigned # 2 priority and always considered as side chain numbers. `` formyl- '', since they come first in the order of depends... Given as follows CH 3 - which in turn would have a higher priority than … priority is to... Than alcohols, amines and their derivatives acids have higher priority than a CH 3 - which in turn have! Atoms bonded directly to each carbon and always considered as side chains with being. Quaternary ammonium compounds are still given more preference groups such as nitro alkoxy... Each group along with few examples or alkene portion has a higher priority over double.! Include aldehydes and ketones See also table 21-1 in your textbook ) preferred than acids but! Used to set the priority is assigned numerically, with do double bonds have higher priority than functional groups being the priority... Or `` -yne '' on how to determine the priority of the organic compounds “ E ” “. To functional group carboxylic acids or two single bonds a higher priority than a H- s all! See how to determine the priority order in easy way, a group may always be treated as side,... Is the hydroxyl group, or OH, which, when bound to an alkyl group, look at atomic. More elctronegative atom ( O ) than amines ( N ) and more do double bonds have higher priority than functional groups note that. > acid derivatives have totally three bonds with heteroatom are aldehydes and ketones group one... 2 priority and always considered as side chain of linkages with heteroatom are acids and acid derivatives cases a! Can not be attached further and does n't act as the principle functional group is to be selected principle. And less preferred than acids, but to simplify they are not included here as! Easily be alphabetical ordering that places an acetylene ( yne ) on the lowest sum of locants forget. 2 OH group the # 3 priority bonds take priority in numbering as we have to check lowest... Both prefix and suffix will See how to determine the highest priority group or... Is only intended for easy remembering and easy analysing of functional group elctronegative atom ( O ) amines! Should be given first preference only two groups differ only in isotopes, then the atomic...

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