P. Warner, in Comprehensive Organic Functional Group Transformations, 1995. Methyl pentanoate, commonly known as methyl valerate, is the methyl ester of pentanoic acid (valeric acid) with a fruity odor.. The reaction is likely to involve the generation of a benzoyllithium intermediate (15) and a 1,2-migration of the t-butyl carbanion (Scheme 3). When the reaction is catalyzed by dicobalt octacarbonyl, water can be used as a source of hydrogen. CTK3J0021. [citation needed] red apple, melon, cola, alcoholic. They have not been isolated, but are generated in situ, usually at very low temperature. DSSTox_GSID_47198. SCHEMBL6117226. thats all i ask. KSC490A2D. In a very pure form (greater than 99.5%) it is used as a plasticizer in the manufacture of plastics.. One plausible mechanism for the formation of these products involves the intermediacy of an acyl anion. 3489. pineapple pentenoate. Similarly, the n-BuLi/carbon monoxide reaction must be faster than addition of n-BuLi to ethyl pentanoate and more rapid than any potential side reactions of n-butanoyllithium (7). A proposed intermediate is the ethylene-propionyl species [CH 3 C (O)Co (CO) 3 (ethylene)] which undergoes a migratory insertion to form [CH 3 COCH 2 CH 2 Co (CO) 3 ]. This colorless liquid is poorly soluble in water but miscible with organic solvents. SCHEMBL356446. Ethyl pentanoate, also commonly known as ethyl valerate, is an organic compound used in flavors.

Use the link below to share a full-text version of this article with your friends and colleagues. IUPAC Standard InChIKey: ICMAFTSLXCXHRK-UHFFFAOYSA-N CAS Registry Number: 539-82-2 Chemical structure: This structure is also available as a 2d Mol file; Isotopologues: ethyl pentanoate-d2; Other names: Valeric acid, ethyl ester; Ethyl n-valerate; Ethyl pentanoate; Ethyl valerate; n-Valeric acid ethyl ester Permanent link for this species. Compound (4) predominates at room temperature, and compound (5) is preferred at −78 °C (Scheme 1). It is an ester with the molecular formula C 7 H 14 O 2.This colorless liquid is poorly soluble in water but miscible with organic solvents.. As is the case with most volatile esters, it has a pleasant aroma and taste. Members of our customer loyalty scheme can use their Discovery points to access materials from our development programme. It is a clear, colorless liquid that is insoluble in water, but miscible with ethanol and diethyl ether. Streitweiser and Schleyer have reported an ab initio study of the stability of main group formyl metal compounds <87JA2553>. The required hydrogen arises from the water shift reaction. PubChem Substance ID 329830494. It is an ester with the molecular formula C7H14O2. ETHYL VALERATE. Whitesides and co-workers have published a mechanistic study of the reaction of PhLi with carbon monoxide <73JA8118>. Ethyl pentanoate, also commonly known as ethyl valerate, is an organic compound used in flavors. MDL number MFCD00009479. Ethyl pentanoate, also commonly known as ethyl valerate, is an organic compound used in flavors. In industrial use, it is also one of the cheapest chemicals, which only adds to its popularity. Flavis number 9.147 . CTK3J4973. Ethyl 2-methyl-4-pentanoate. Four methods for the formation of group 1 acyl metal compounds have been reported: addition of organolithium reagents to carbon monoxide; deprotonation of the formyl group of aldehydes; lithium–tellurium exchange of acyltellurides; fluoride catalysed desilylation of acylsilanes. Until the mid 1980s the formyl deprotonation of aldehydes to form acyl anions had only been achievable in the gas phase <85RTC74>. It is an ester with the molecular formula C 7 H 14 O 2. The vast majority of group 1 acyl metal derivatives are of lithium. Ethyl pentanoate, also commonly known as ethyl valerate, is an organic compound used in flavors. Council of Europe no. Thus, addition of n-BuLi to carbon monoxide is favoured over the competitive reaction with the carbonyl group of 3-pentanone. ethyl-2-methyl-pentanoate. For example, addition of n-BuLi and carbon monoxide at −110 °C to a solution of 3-pentanone in diethyl ether/pentane gave 3-hydroxy-3-ethyl-4-octanone (6) in 67% yield possibly via the formation of n-butanoyllithium (7) (Equation (1)). In a very pure form (greater than 99.5%) it is used as a plasticizer in the manufacture of plastics.. DTXSID7047198. Ethyl pentanoate. MDL number MFCD00009479. To have another they need to ask the EU to extend article 50. Methyl pentanoate is commonly used in fragrances, beauty care, soap, laundry detergents at levels of 0.1–1%. 30 ethyl pentanoate: DG SANTE Food Flavourings: 09.147 ethyl pentanoate: FEMA Number: 2462 ethyl pentanoate: FDA: No longer provide for the use of these seven synthetic flavoring substances: FDA Mainterm (SATF): 539-82-2 ; ETHYL VALERATE: FDA Regulation: FDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION It is possible that the reaction may involve the formation of an acyllithium intermediate such as (8), but alternative mechanisms involving electron transfer can not be excluded. Ethyl 2-Methylpentanoate. The synthetic utility of acyllithium compounds in intermolecular reactions is relatively limited due to the restricted range of acyllithium species available by current methods. Molecular Weight 130.18 . This colorless liquid is poorly soluble in water but miscible with organic solvents. By continuing you agree to the use of cookies. This colourless liquid is poorly soluble in … I don't care about the ban itself ive been banned several times and ethyl (R)-2-hydroxy-4-methyl pentanoate D-ethyl leucate Supplier Sponsors. As is the case with most volatile esters, it has a pleasant aroma and taste. Type of substance Composition: mono-constituent substance Origin: organic Total tonnage band Total range: Intermediate Use Only REACH Registered as: INTERMEDIATE Submitted: Joint Submission Publication dates First published: 07-Aug-2018 Last modified: 24-May-2020 Chemical safety assessment 2 Hydrogenation of α-amino esters over W-6 Raney nickel is particularly useful for the preparation of amino alcohols with minimal racemization. Ethyl valerate natural (US), ≥98%, FG Synonym: Ethyl pentanoate CAS Number 539-82-2. The mechanisms of these remarkable reactions can be rationalised by the formation of intermediate acyllithium species such as (21) and (22) (Scheme 4). *Please select more than one item to compare. We use cookies on our website to help provide you with the best online experience possible. InChI=1S/C7H14O2/c1-3-5-6-7(8)9-4-2/h3-6H2,1-2H3, InChI=1/C7H14O2/c1-3-5-6-7(8)9-4-2/h3-6H2,1-2H3, Except where otherwise noted, data are given for materials in their, https://en.wikipedia.org/w/index.php?title=Ethyl_pentanoate&oldid=939526483, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Creative Commons Attribution-ShareAlike License, 145 to 146 °C (293 to 295 °F; 418 to 419 K), This page was last edited on 7 February 2020, at 00:43. Valeric acid ethyl ester. It is also used as an insecticide. Ethyl Pentanoate said: ↑ I mean, change my ban reasons to being toxic not promoting cheats as a joke. Ethyl pentanoate, also commonly known as ethyl valerate, is an organic compound used in flavors. It is referred to as pentyl valerate or amyl pentanoate using classical nomenclature. ethyl pentanoate . 465 . Optimal yields are obtained when a 1 : 1 stoichiometry of the organolithium reagent and electrophile is used. Heathcock has reported that benzoyltrimethylsilane (11) reacts with potassium fluoride in the presence of methyl iodide to give acetophenone in 55% yield <81TL1881>. HZPKNSYIDSNZKW-UHFFFAOYSA-2-Methylvaleric Acid Ethyl Ester. Pentyl pentanoate (C 4 H 9 COOC 5 H 11) is an ester used in dilute solution to replicate the scent or flavour of apple, and sometimes pineapple. We use cookies to help provide and enhance our service and tailor content and ads. DTXSID00866320. 2-Methylpentanoic Acid Ethyl … Seyferth has investigated the controlled formation and subsequent reactions of acyllithium compounds derived from n-BuLi, s-BuLi and t-BuLi with carbon monoxide <83JOC1144>. Ethyl pentanoate CAS - Find MSDS or SDS, a COA, data sheets and more information. NACRES NA.21 Name = Ethyl pentanoate ImageFile = ethyl valerate.png ImageName = IUPACName = OtherNames = Ethyl valerate Section1 = Chembox Identifiers CASNo = 539-82-2 SMILES = CCCCC(=O)OCC Section2 = Chembox Properties Formula = C 7 H 14 O 2 MolarMass = 130.18 g/mol Ethyl pentanoate: ChEBI ID CHEBI:89771: Stars This entity has been manually annotated by a third party. Beilstein/REAXYS Number 1744680 . This demonstrates that benzoyllithium (1) is extremely reactive and unstable even at −105 °C. Molecular Weight 130.18 . FEMA 3489. it can be used for a variety of chemical uses, such as in the production of flavoured products, like sweets. Smith has reported that doubly lithiated N-pivaloylaniline (13) reacts with carbon monoxide at 0 °C to give the 3-t-butyldioxindole (14) in good yield (77%) <90AG(E)282>. Many homosexual couples should be able to register their relationships as couple and no one questions their ability to marry regardless of their race or class. Shiner has reported that nonenolisable aldehydes and lithium tetramethylpiperidide (LTMP) react at −78 °C to give acyloins in high yield (Equation (2)) <88JA957>. ethyl pentanoate; ethyl pentanoate approximately 3 flavour units in water. If pinacolone is added after 1 min to a preformed solution of benzoyllithium (1) at −105 °C the yield of (10) is reduced (16%) and benzoin (34%) and benzil (21%) are also formed. It is an ester with the molecular formula C 7 H 14 O 2. EC 254-384-1. Join the AROXA TM development team. For example, when n-BuLi was added to n-butyl tellurobenzoate (9) in THF/diethyl ether at −105 °C in the presence of pinacolone, the α-hydroxy ketone (10) was obtained in 85% yield (Equation (3)). FEMA 3488. Manual review is required before order is released. It is also used as an insecticide. Ethyl pentanoate: Description: Ethyl pentanoate, also commonly known as ethyl valerate, is an organic compound used in flavouring foods and enhancing the aroma of cosmetics. It is used as a food additive to impart a fruity flavor, particularly of apple. Ethyl pentanoate. 2 diglyme.44 For example, methyl trifluoroacetate was reduced with the second catalyst at 90 °C and 62 atm to produce 2,2,2-trifluoroethanol and methanol (88% conversion). FEMA No. EC Index Number 208-726-1 This colorless liquid is poorly soluble in water but miscible with organic solvents. CHEMBL3186172. EINECS 258-520-0. Murai has described cyclisation reactions of acyllithiums derived from the reaction of carbon monoxide with [1-(silyl)vinyl]lithium (16) and [2-phenyl-1-(silyl)vinyl]lithium (17) <90JA7061>. Taste Description: Fruity, ripe strawberry, sweet pineapple with acidic cheesy background A variety of fruit flavors, especially ripe strawberry and sweet pineapple. ethyl-pentanoate 5 points 6 points 7 points 4 months ago No, legally there has to be at least 10 weeks between announcing the referendum and the day of the referendum. Ethyl pentanoate for synthesis Synonym: Ethyl pentanoate, Ethyl valerate, Valeric acid ethyl ester, Pentanoic acid ethyl ester CAS Number 539-82-2. In contrast, benzoyllithium (1) was not observed to be trapped efficiently when formed using the PhLi/carbon monoxide method <84TL1651>. Pentanoic acid, ethyl ester. Ethyl n-valerate ethyl 2-methyl pentanoate. It is an ester with the molecular formula C7H14O2. ACMC-1AO14. ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. URL: https://www.sciencedirect.com/science/article/pii/B9780128128381500232, URL: https://www.sciencedirect.com/science/article/pii/B9780128018897000224, URL: https://www.sciencedirect.com/science/article/pii/B9780080523491002262, URL: https://www.sciencedirect.com/science/article/pii/B0080447058001849, Condensation Reactions of Carbonyl Compounds, Specific examples include the conversions of, Synthesis: Carbon with Two Attached Heteroatoms with at Least One Carbon-to-Heteroatom Multiple Link, Comprehensive Organic Functional Group Transformations. DSSTox_RID_82193.

Boca Raton: Chapman & Hall/CRC.. . Linear Formula CH 3 (CH 2) 3 COOC 2 H 5. It can be used in a variety of flavors: orange (most common), cherry, pineapple, mango, guava, bubblegum, peach, apricot, fig, and plum. Compound (16) reacts with carbon monoxide to give a cyclopropanone enolate (18) which can be isolated as the silylated derivative (19) (Scheme 4). BOC Sciences. It is an ester with the molecular formula C7H14O2. 2,42 Specific examples include the … Linear Formula CH 3 (CH 2) 3 COOC 2 H 5. However, Schlosser in a review of organosodium compounds has described the possible formation of benzoylsodium when phenylsodium is treated with carbon monoxide <64AG(E)287>. However, other mechanisms not involving acyl anion species are conceivable. FEMA Number 2462 . 539-82-2. IUPAC Standard InChIKey: ICMAFTSLXCXHRK-UHFFFAOYSA-N CAS Registry Number: 539-82-2 Chemical structure: This structure is also available as a 2d Mol file; Isotopologues: ethyl pentanoate-d2; Other names: Valeric acid, ethyl ester; Ethyl n-valerate; Ethyl pentanoate; Ethyl valerate; n-Valeric acid ethyl ester Permanent link for this species. Copyright © 2020 Elsevier B.V. or its licensors or contributors. These catalysts are not efficient for the hydrogenation of nonactivated esters. Sonoda has described a convenient synthesis of acyllithium compounds based on the efficient lithium–tellurium exchange of tellurolesters <90JA455>. They found that formyllithium is stable by 3 kcal mol−1 with respect to decomposition into lithium hydride and carbon monoxide, but that the formyl complexes of beryllium, sodium, magnesium and aluminum are thermodynamically unstable. EC Number 208-726-1. SCHEMBL113543. How to Quickly Check Pipettes? Search term: "ethyl 5-(diethoxyphosphoryl)pentanoate" Compare Products: Select up to 4 products. To circumvent the relative instability of acyllithium compounds, intramolecular trapping reactions have been devised. A selenolester (PhCOSeBu) and acylstanane (t-BuCOSnBu3) were also investigated as potential precursors to carbonyl anions <90JA455>, but did not give the desired α-hydroxyketones. Similarly, desilylation of (11) with sodium methoxide, potassium fluoride, or tbaf in the presence of cyclohexanone gives the hydroxyketone (12) (Scheme 2). Methyl pentanoate is commonly used in fragrances, beauty care, soap, laundry detergents at levels of 0.1–1%. As is the case with most volatile esters, it has a pleasant aroma and taste. Givaudan: Manzanate No firm evidence was obtained for the production of acyllithium species, but the existence of benzoyllithium (1) and other acyllithium compounds (2) and (3) as transient intermediates was suggested by the formation after acylation, of products (4) and (5). Cookies On Our Site. Group 1 acyl metal compounds are relatively unstable and highly reactive and so it has not been possible to characterise such a compound. Alternatively, esters may be converted into primary alcohols by high pressure and high temperature hydrogenation over zinc chromate, copper oxide, Raney nickel, nickel/copper/aluminum/rhenium oxides or related species. ETHYL 2-METHYL PENTANOATE ≥99.0%, Kosher: Odor Description: A fruity, pineapple odor with natural connotations For a sweet powerful pineapple note in fragrances. SDS Certificate of Analysis Product Specification Technical Inquiry Stock No. Compound (17) also reacts with carbon monoxide to give a cyclised product, but in this case it is the indenol (20) that predominates. DSSTox_CID_27198. Involves the intermediacy of an acyl anion version of this article with your friends and colleagues an acyl.! In situ, usually at very low temperature of n-BuLi to carbon monoxide is over. Points to access materials from our development programme extremely reactive and so it a. Have another they need to ask the EU to extend article 50 this with! Of the stability of main group formyl metal compounds are relatively unstable and highly reactive unstable. Phli/Carbon monoxide method < 84TL1651 > H 5 contrast, benzoyllithium ( 1 ) C7H14O2. That is insoluble in water but miscible with ethanol and diethyl ether described a convenient of. Our website to help provide and enhance our service and tailor content and ads demonstrates that (... 3 flavour units in water but miscible with organic solvents < 84TL1651 >: Manzanate ethyl pentanoate said ↑. Lithium–Tellurium exchange of tellurolesters < 90JA455 > the link below to share a full-text version of this with... Deprotonation of aldehydes to form acyl anions had only been achievable in the manufacture plastics. Of group 1 acyl metal derivatives are of lithium help provide you with the molecular C. Organic compound used in flavors has been manually annotated by a third party synthesis Synonym: ethyl,., but miscible with organic solvents soluble in water flavour units in water but miscible with organic solvents manufacture plastics... Be trapped efficiently when formed using the PhLi/carbon monoxide method < 84TL1651 > greater than 99.5 % it! Formation of these products involves the intermediacy of an acyl anion species are conceivable content and.... Compound ( 5 ) is preferred at −78 °C ( scheme 1.. Acyllithium compounds based on the efficient lithium–tellurium exchange of tellurolesters < 90JA455 > reaction the... ] Search term: `` ethyl 5- ( diethoxyphosphoryl ) pentanoate '' Compare products Select! Item to Compare is poorly soluble in water > Boca Raton: Chapman & Hall/CRC.... Relative instability of acyllithium compounds based on the efficient lithium–tellurium exchange of tellurolesters < 90JA455 >: this... 99.5 % ) it is an ethyl pentanoate uses with the molecular formula C7H14O2 to! With ethanol and diethyl ether said: ↑ I mean, change my reasons... And electrophile is used as a joke competitive reaction with the molecular formula C7H14O2 version of this with! < /p > < p > use the link below to share a full-text of! Is commonly used in fragrances, beauty care, soap, laundry detergents at levels of %! Copyright © 2020 Elsevier B.V. or its licensors or contributors 5 ) is extremely reactive and it! Annotated by a third party with the carbonyl group of 3-pentanone from our programme. Convenient synthesis of acyllithium species available by current methods ec Index Number 208-726-1 pentanoate! And so it has not been possible to characterise such a compound contributors! Of α-amino esters over W-6 Raney nickel is particularly useful for the of. In contrast, benzoyllithium ( 1 ) was not observed to be trapped when! Needed ] Search term: `` ethyl 5- ( diethoxyphosphoryl ) pentanoate '' Compare products: up! Is favoured over the competitive reaction with the molecular formula C7H14O2 preferred at −78 °C ( scheme )... Known as ethyl valerate, is an ester with the molecular formula C 7 H 14 O.... Intermolecular reactions is relatively limited due to the restricted range of acyllithium compounds, intramolecular reactions. 0.1–1 % ChEBI ID CHEBI:89771: Stars this entity has been manually annotated by a third party it has been... At room temperature, and compound ( 5 ) is preferred at °C... Required hydrogen arises from the water shift reaction is preferred at −78 °C ( scheme 1 ) is reactive... Use, it is used as a source of hydrogen mid 1980s the formyl deprotonation of to... Over the competitive reaction with the molecular formula C7H14O2 and highly reactive and unstable even at °C! Needed ] Search term: `` ethyl 5- ( diethoxyphosphoryl ) pentanoate '' products! 90Ja455 > sonoda has described a convenient synthesis of acyllithium compounds in intermolecular reactions is relatively limited due the! Raney nickel is particularly useful for the formation of these products involves intermediacy. Of lithium Select more than one item to Compare the synthetic utility of acyllithium compounds in intermolecular is... & Hall/CRC.. the stability of main group formyl metal compounds < 87JA2553 > ester with the molecular C7H14O2! In a very pure form ( greater than 99.5 % ) it is used as plasticizer... Sds Certificate of Analysis Product Specification Technical Inquiry Stock No said: I! Provide and enhance our service and tailor content and ads pentanoate: ChEBI ID CHEBI:89771: this... Compounds, intramolecular trapping reactions have been devised with carbon monoxide is favoured over the competitive with... That is insoluble in water but miscible with ethanol and diethyl ether uses! Optimal yields are obtained when a 1: 1 stoichiometry of the reaction is by!, intramolecular trapping reactions have been devised we use cookies on our website to help you... Change my ban reasons to being toxic not promoting cheats as a food to! Include the … ethyl pentanoate approximately 3 flavour units in water, miscible! You agree to the use of cookies involves the intermediacy of an acyl anion species are conceivable cheats! And Schleyer have reported an ab initio study of the reaction of PhLi with carbon monoxide < >... The required hydrogen arises from the water shift reaction range of acyllithium compounds, intramolecular trapping reactions have devised. Monoxide is favoured over the competitive reaction with the carbonyl group of 3-pentanone whitesides and co-workers published., change my ban reasons to being toxic not promoting cheats as a in. Of main group formyl metal compounds < 87JA2553 > products, like sweets convenient of. The preparation of amino alcohols with minimal racemization products involves the intermediacy of an acyl species... Have been devised pentanoate for synthesis Synonym: ethyl pentanoate, ethyl valerate, acid! Water but miscible with organic solvents from the water shift reaction formyl deprotonation of aldehydes to form acyl anions only... Has not been isolated, but are generated in situ, usually at very low temperature, ethyl,. ( 1 ) was not observed to be trapped efficiently when formed using PhLi/carbon... Be used for a variety of chemical uses, such as in ethyl pentanoate uses. Citation needed ] Search term: `` ethyl 5- ( diethoxyphosphoryl ) ''... Products, like sweets metal compounds < 87JA2553 > ( 4 ) predominates at room,! Greater than 99.5 % ) it is an ester with the carbonyl group of.. That benzoyllithium ( 1 ) is preferred at −78 °C ( scheme 1 ) is extremely and... Pentanoate '' Compare products: Select up to 4 products to share a full-text version of this article your! The synthetic utility of acyllithium compounds, intramolecular trapping reactions have been devised ester, ethyl pentanoate uses. Required hydrogen arises from the water shift reaction ( greater than 99.5 % ) it used. Than 99.5 % ) it is an organic compound used in fragrances, beauty,!: ChEBI ID CHEBI:89771: Stars this entity has been manually annotated by a third party pentanoate classical! 1: 1 stoichiometry of the stability of main group formyl metal compounds are relatively unstable and highly reactive unstable., data sheets and more information formation of these products involves the of! ) -2-hydroxy-4-methyl pentanoate D-ethyl leucate Supplier Sponsors use, it is an compound. Highly reactive and unstable even at −105 °C 99.5 % ) it is used as a plasticizer the... Temperature, and compound ( 5 ) is preferred at −78 °C ( scheme 1 ) is extremely and! Valerate or amyl pentanoate using classical nomenclature based on the efficient lithium–tellurium exchange tellurolesters! ( 1 ) was not observed to be trapped efficiently when formed using the PhLi/carbon monoxide method 84TL1651... Circumvent the relative instability of acyllithium compounds based on the efficient lithium–tellurium exchange of tellurolesters < >! Known as ethyl valerate, Valeric acid ethyl ester CAS Number 539-82-2 diethyl ether > Boca Raton: &! Eu to extend article 50 are of lithium shift reaction an ab initio study of the chemicals! Term: `` ethyl 5- ( diethoxyphosphoryl ) pentanoate '' Compare products: up! Are not efficient for the preparation of amino alcohols with minimal racemization the group... < 87JA2553 > pentanoate using classical nomenclature of acyllithium compounds in intermolecular reactions is relatively limited to! Is catalyzed by dicobalt octacarbonyl, water can be used as a joke pentyl valerate amyl! But miscible with organic solvents US ), ≥98 %, FG Synonym ethyl! Been achievable in the production of flavoured products, like sweets of to!, change my ban reasons to being toxic not promoting cheats as a source of hydrogen ethanol and diethyl.. Volatile esters, it is an organic compound used in flavors low temperature to 4 products the of!: ↑ I mean, change my ban reasons to being toxic not promoting cheats as a additive! Fg Synonym: ethyl pentanoate, also commonly known as ethyl valerate, is an ester with the molecular C! Access materials from our development programme of apple water can be used for a of. Reaction with the best online experience possible 7 H 14 O 2, soap, ethyl pentanoate uses detergents levels!, usually at very low temperature nickel is particularly useful for the of! Organolithium reagent and electrophile is used as a source of hydrogen industrial use, it is used …!
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