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SaplingChapter14 - Question 1 of 19.flSaph’ng Learning...

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Unformatted text preview: Question 1 of 19 .flSaph’ng Learning For each compound, select all that apply. a) =\ / c\\ conjugated nonconjugated diene triene conjugated nonconjugated diene triene b) c) conjugated nonconjugated —6—6—\\\\\ :1) QK diene triene conjugated nonconjugated diene DUDE] DUDE] DUDE HEIDI] tn'ena Question 2 of 19 IflSapIing Learning Classify each of the four compounds below as a conjugated, isolated, or cumulated diene. O conjugated diene isolated diene cumulated diene conjugated diene isoiated diene cumulated diene b) \— c) \— _ isolated diene cumulated diene conjugated diene d) isolated diene cumulated diene O O O O O O conjugated diene O O O O O Question 3 of 19 Draw the structure! formula of (3E,5Z)-5-ethyl-3.5-nonadiene. Question 4 of 19 IflSopling Learning Draw the addition product formed when one equivaient of HCI reacts with the following diene. H3 HCl —> one equivalent Question 5 of 19 flSapling Learning Draw the addition products formed when one equivaient of HBr reacts with 2,4—hexadiene. (Draw a single product for each. Ignore stereochemical or chiral isomers.) 1,2-addition product: HBr CH3 ——-9 Hsc/W (one equivalent) 1 ,4-addition product: Question 6 of 19 :fl'Sapling Learning _ For each addition route of the reaction. draw the structures of the major products, including stereochemistry. ‘i ,2—addilion: CCl4 1,4—addition: Question 7 of 19 .flSapfing Learning Draw the kinetic and the thermodynamic addition products formed when one equivalent of HBr reacts with the following compound. (Draw a single product for each. Ignore stereochemical or chiral isomers.) kinetic product: H3 HBr l—> (one equivalent) thermodynamic product: Question 8 of 19 IflSapling Learning For the reaction of one equivalent of HG! with butadiene, characten'ze the four structures below as to whether each might be a product of the reaction. and if so, the type of product. (For each sthcture, select all terms that apply.) HCl HZWC H2 __> ? (3| Cl CH3 c/vaHz H3C&/ H3 / not a product not a product 1 ,2-addition 1,2—addition product product 1 ,4-addition 1,4-addition not a product not a product 1 .2—addition 1 ,2—addition product product 1 .4-a‘ddition 1 ,4-addition product product kinetic product kinetic product thermodynamic thermodynamic product product product product kinetic product kinetic product thermodynamic thermodynamic product product Question 9 of 19 IflSapling Learning Draw the structure of the diene that reacts with one equivalent of HBr to form the following two compounds as the only bromoalkene products. Br CH3 CH3 I' H3 C H3 Describe the effect of increasing temperature on the relative amount of each product. Relative amount increases. Relative amount increases. Relative amount Relative amount decreases. Temperature has little effect Temperature has little effect on relative amount. on relative amount. decreases. Question 10 of 19 IflSapling Learning _ Mono addition of HBr to conjugated dienes leads to multi le products, and a given addition product can arise from more than one conjugated diene. Given below are t e structures of five pairs of dienes — possible reactants in the reaction — and two allylic bromide products. Identify the pair of dienes wherein each diene can serve as a precursor for both of the addition products. Note that not all possible products are shown. Possible Precursors of Both Products Mono Addition Products (select one tab as your answer) - .- .- - -—- H3 C H3 H3 BB 1' r H3 Br C H3 H3 —> Question 11 of 19 .flSapling Learning Provide the major product expected for the following reactions. Omit byproducts. Ignore stereochemistry. Question 12 of 19 (CH3)3CO‘K+ —> (CH3)3C0H IflSaph’ng Learning Provide the major product of the following reaction sequence. If cisitrans is possible, draw only the major isomer. If enantiomers are possible. do not specify configuration. NBS hv or ROOR 1) Brz. heat / \ —) 2) 2 equiv. NaCN DMF Question 13 of 19 .flSapling Learning Mono addition of HBr to unsymmetrical dienes generally produces four products — two 1.2-addition roducts and two 1,4—addition products. Draw the reactant diene that forms the following four products, and i entity the addition route that forms each product. Products Formed by Br Reactant Diene O 1.2-addition. (one compound) H3 H3 0 1,4-a‘ddition. l_ ' i | I : ' B. l . | | | _ I o 1.2-addition. I . I I I H3 CH2 I - -- I -— I - - HBr O 1.4-addition. 1 I_____. I I. I —> B. I . I I I W O 1.2-additi'on. I I I I H3 H3 0 1,4-addition. O 1,2—addition. Br chMle O 1,4-addition. Question 14 of 19 IflSaph’ng Learning _ Mono addition of HCI to unsymmetrical dienes generally produces four products — two 1,2—addition products and two 1.4-addition products. In some cases, such as the following, a 1.2»addition product and a 1.4-addition product may have the same structure. and thus only three distinct products are formed. Draw the reactant diene that forms the following three products, and identify the addition route that forms each product. Products Formed by 1 ,2-add ition. 1 ,4~addition. both routes. Reactant Diene (one compound) 1 ,2-addition. 1 .4-addition. both routes. 1 .2-addition. 1 ,4—addition. both routes. Question 15 of 19 IflSapIing Learning I For the following Diels— Alder reaction, the product skeletal structure and configuration at the bridgehead carbons are given (and the given wedge bond and dash bond should not be changed). Complete the structure of the major product. Indicate the stereoohemistry, by adding two wedge and two dash bonds. at only the fused-ting stereocenters, which are highlighted green. Question 16 of 19 IflSapHng Learning in the product of the Diels— Alder reaction below. highlight — by clicking on — the newly formed 0 bonds. Question 17 of 19 IflSaphng Learning Add curved arrows to the reactants to show the formation of new bonds and the breaking of old bonds for the following Dials—Alder reaction. A double-barbed curved arrow is used to represent the movement of a pair 0 e ectrons. Question 18 of 19 IflSaphng Learning Complete the drawing of the product of the Diets—Alder reaction, ignoring stereochemistry. K 0 + 0 _> _o 0—: Question 19 of 19 IflSapfing Learning The Diets— Alder reaction between butadiene and dimethyl maleate ields a ring structure, as shown in the product below. Complete the structure by drawing any missing ban 5 and indicating the stereochemistry of the new stereocenters. CH2 \ 0‘3 a n ...
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