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Part II (45) Answer any five of the following nine questions. There is no penalty for...
1. Consider the following substituted alkanes. Indicate if the molecule would prefer to undergo an SN1...
1. Consider the following substituted alkanes. Indicate if the molecule would prefer to undergo an SN1 reaction, an reaction, BOTH S1/E1 or neither: -BOK 2. Briefly explain why you selected what you did for question 1a, 1b, and 1c. 3. Provide the missing reactant(s) or product(s) as necessary for the following Sy1 reactions. Be sure to use wedges/dashes to indicate stereochemistry where relevant. осн. HOCH,CH, heat 4. Draw the complete mechanism for the following reaction. Include all lone pairs, formal...
(C) Protonation of alkene to form a carbocation followed by addition of bromide ion (D) Addition...
(C) Protonation of alkene to form a carbocation followed by addition of bromide ion (D) Addition of the proton to one face of the alkene with simultaneous delivery of a bromide ion from a different molecule of H-Br. 11. Which compound is the strongest nmucleophile for reaction of methane methanesulfonate (CHOS0.CH) in methanol at room temperature? (You may assume that everything is soluble in methanol) (A) potassium bromide (B) cesium iodide (C) sodiam chloride (D) lithium flaoride 12. Which proton...
(Cp 4) For the structure shown below, use one of the templates to show the Newman...
(Cp 4) For the structure shown below, use one of the templates to show the Newman projection which corresponds to the view down the bold bond. In the Newman projection you need only show the atoms attached directly to the carbons connected by the bold bond (and not the remainder of the ring). If there is a more stable conformation for the molecule, draw it in the box to the right (do not give a Newman projection for the more...
99 - Synthesis questions. now the starting material can be converted to the product through any of the reactions y...
99 - Synthesis questions. now the starting material can be converted to the product through any of the reactions you med in Chem-I. Show all the reagents you need and indicate the stereochemistry when opriate. You do not need to show arrow pushing like in a mechanism question, only the eactions. If a chiral molecule is formed mark the chiral center with an asterisk (°) and write below the structure. You may also draw both enantiomers and write RACEMIC in...
1. Draw the structures of: a) (Z) 2-iodo-3-methyl-2-heptene b) cis non-3-en-5 yne Give the IUPAC name...
1. Draw the structures of: a) (Z) 2-iodo-3-methyl-2-heptene b) cis non-3-en-5 yne Give the IUPAC name of the following compounds, including steochemistry. a) F CH2CH2Br CH3CE 2. a) Draw the most stable chair conformation of cis 1,3-difluorocyclohexane. b) Draw a Newman projection of 2-iodo-3-methylpentane looking down the 3. Compound X has the formula CoHB2Br4. Compound X reacts with excess H2/Pd to give CATHa6Bra. How many does compound X have? Show how you got your answer. rings 4. For each pair...
2. When both the diene and dienophile are unsymmetrical, then regiochemistry becomes an issue. In this...
2. When both the diene and dienophile are unsymmetrical, then regiochemistry becomes an issue. In this case, it is helpful to remember that when you number the diene and dienophile, that carbon 1 of the diene can either attach to carbon 6 or to carbon 5 of the dienophile: 1 1 2 4 2 6 2 5 1 5 3 3 5 3 6 4 4 In on top of this, you still need to think about the different possible...
Use the Fischer projection below to answer the following questions сн. Br- H H- Br CH,CH,...
Use the Fischer projection below to answer the following questions сн. Br- H H- Br CH,CH, (a) Write the IUPAC name for this molecule using the R/S notation (b) Draw the skeletal structure of the mirror Image, le the enantiomer, of the molecule whose Fischer projection is given above. (Show one wedge bond, one dashed bond, and two sticks attached to the chiral carbon. Show the hydrogen atom bonded to the chiral carbon atom as either a wedge or dash...
2. List the trend of relative reactivity of compounds in: SN2 & SN1. Indicate which favors...
2. List the trend of relative reactivity of compounds in: SN2 & SN1. Indicate which favors 1°, 2° or 3° carbon. 3. What makes a good leaving group, or poor leaving group in a substitution reaction? List examples. 4. What makes a good nucleophile or poor nucleophile group in a substitution reaction? List examples. Be able to identify the nucleophile in a reaction. 5. What makes a good solvent for an SN2 reaction? List examples. Assign R & S to...
4. Povide reasonable prodact strctaes or ch of the fellowing reation Nae D NaN oso,CH PP...
4. Povide reasonable prodact strctaes or ch of the fellowing reation Nae D NaN oso,CH PP Pvide nonable prodct trectures Na Br ot ielated Povide reasonablle product sructares For cach one briefly esplain your choice of segioisoers нс с, сн, вве D сн, D-Br нс ст, 7. Povide the structase of likely products from the following reactions. Indicate if you expect enantiomers, diasteromens, acither, or both Use wedges and dashes to indicate the steochemistry when it is important LHgOA но...
Name Stereoisomers and Chirality Worksheet 1) Consider the molecules drawn below a) Idently all he chiral...
Name Stereoisomers and Chirality Worksheet 1) Consider the molecules drawn below a) Idently all he chiral carbons in the following molecules and put an () next to them он NH2 NH2 NH2 Glycine Isoleucine Leucine HO lbuprofern Morphine Ho Cocaine ethambutol b) How many total stereoisomers are possible for each of the compounds above (put the number next to the structure somewhere)? 2) Draw all possible stereoisomers of 1.2-dimethy)cyclopentane in the space below. Be sure to include 3-D information using...
1. Consider the following substituted alkanes. Indicate if the molecule would prefer to undergo an SN1 reaction, an reaction, BOTH S1/E1 or neither: -BOK 2. Briefly explain why you selected what you did for question 1a, 1b, and 1c. 3. Provide the missing reactant(s) or product(s) as necessary for the following Sy1 reactions. Be sure to use wedges/dashes to indicate stereochemistry where relevant. осн. HOCH,CH, heat 4. Draw the complete mechanism for the following reaction. Include all lone pairs, formal...
(C) Protonation of alkene to form a carbocation followed by addition of bromide ion (D) Addition of the proton to one face of the alkene with simultaneous delivery of a bromide ion from a different molecule of H-Br. 11. Which compound is the strongest nmucleophile for reaction of methane methanesulfonate (CHOS0.CH) in methanol at room temperature? (You may assume that everything is soluble in methanol) (A) potassium bromide (B) cesium iodide (C) sodiam chloride (D) lithium flaoride 12. Which proton...
(Cp 4) For the structure shown below, use one of the templates to show the Newman projection which corresponds to the view down the bold bond. In the Newman projection you need only show the atoms attached directly to the carbons connected by the bold bond (and not the remainder of the ring). If there is a more stable conformation for the molecule, draw it in the box to the right (do not give a Newman projection for the more...
99 - Synthesis questions. now the starting material can be converted to the product through any of the reactions you med in Chem-I. Show all the reagents you need and indicate the stereochemistry when opriate. You do not need to show arrow pushing like in a mechanism question, only the eactions. If a chiral molecule is formed mark the chiral center with an asterisk (°) and write below the structure. You may also draw both enantiomers and write RACEMIC in...
1. Draw the structures of: a) (Z) 2-iodo-3-methyl-2-heptene b) cis non-3-en-5 yne Give the IUPAC name of the following compounds, including steochemistry. a) F CH2CH2Br CH3CE 2. a) Draw the most stable chair conformation of cis 1,3-difluorocyclohexane. b) Draw a Newman projection of 2-iodo-3-methylpentane looking down the 3. Compound X has the formula CoHB2Br4. Compound X reacts with excess H2/Pd to give CATHa6Bra. How many does compound X have? Show how you got your answer. rings 4. For each pair...
2. When both the diene and dienophile are unsymmetrical, then regiochemistry becomes an issue. In this case, it is helpful to remember that when you number the diene and dienophile, that carbon 1 of the diene can either attach to carbon 6 or to carbon 5 of the dienophile: 1 1 2 4 2 6 2 5 1 5 3 3 5 3 6 4 4 In on top of this, you still need to think about the different possible...
Use the Fischer projection below to answer the following questions сн. Br- H H- Br CH,CH, (a) Write the IUPAC name for this molecule using the R/S notation (b) Draw the skeletal structure of the mirror Image, le the enantiomer, of the molecule whose Fischer projection is given above. (Show one wedge bond, one dashed bond, and two sticks attached to the chiral carbon. Show the hydrogen atom bonded to the chiral carbon atom as either a wedge or dash...
2. List the trend of relative reactivity of compounds in: SN2 & SN1. Indicate which favors 1°, 2° or 3° carbon. 3. What makes a good leaving group, or poor leaving group in a substitution reaction? List examples. 4. What makes a good nucleophile or poor nucleophile group in a substitution reaction? List examples. Be able to identify the nucleophile in a reaction. 5. What makes a good solvent for an SN2 reaction? List examples. Assign R & S to...
4. Povide reasonable prodact strctaes or ch of the fellowing reation Nae D NaN oso,CH PP Pvide nonable prodct trectures Na Br ot ielated Povide reasonablle product sructares For cach one briefly esplain your choice of segioisoers нс с, сн, вве D сн, D-Br нс ст, 7. Povide the structase of likely products from the following reactions. Indicate if you expect enantiomers, diasteromens, acither, or both Use wedges and dashes to indicate the steochemistry when it is important LHgOA но...
Name Stereoisomers and Chirality Worksheet 1) Consider the molecules drawn below a) Idently all he chiral carbons in the following molecules and put an () next to them он NH2 NH2 NH2 Glycine Isoleucine Leucine HO lbuprofern Morphine Ho Cocaine ethambutol b) How many total stereoisomers are possible for each of the compounds above (put the number next to the structure somewhere)? 2) Draw all possible stereoisomers of 1.2-dimethy)cyclopentane in the space below. Be sure to include 3-D information using...
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