Q4 all c2210 11 w17 - Organic Chemistry I, Quiz 4 Fall 2017 PDF

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Organic Chemistry I, Quiz 4 Fall 2017...

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CHM 2210 Mar 23, 2017 PRINTED NAME: __________________________________________________________ Rec. Sec. No. 12 & 15 Quiz 4A BlackBoard Login ____________________ SIGNED NAME: ___________________________________________________________ To earn full credit, provide all the information requested above. Clearly give your answers in the spaces provided. ***DO NOT WRITE ANYTHING ON THE BACK OF THIS SHEET. Do not ask anyone to explain any problem to you. Read the problem carefully and interpret its meaning. 1.

[9 points] For each of the following, choose the best answer; give the letter. (i) Which reacts faster with NaI in acetone: (a) trans-1-bromo-3-methylcyclopentane or (b) 1-bromo-1-methylcyclopentane? (ii) Which reaction with NaSCH3 is slower: (a) (R)-2-bromohexane in DMSO or (b) (R)-2-iodohexane in DMSO? (iii) Which type of solvent is acetic acid best described as:

(a) nonpolar; (b) polar protic; or (c) polar aprotic ?

2.

1i)

2)

[6 points] Provide an efficient multistep synthesis for the following conversion of the given starting material into target compound. For each functional group transformation, give all necessary reagents and catalysts and give a structural formula of the major organic product. Also give hv and/or heat when necessary. Show stereochemistry appropriately when necessary. If a racemic mixture is formed, give structural formulas for both enantiomers. If a mixture of products must be present after a step, assume that you can separate the mixture and take the one needed product forward through the next step.

1ii)

1iii)

CHM 2210 Mar 23, 2017 PRINTED NAME: __________________________________________________________ Rec. Sec. No. 13 & 16 Quiz 4B BlackBoard Login ____________________ SIGNED NAME: ___________________________________________________________ To earn full credit, provide all the information requested above. Clearly give your answers in the spaces provided. ***DO NOT WRITE ANYTHING ON THE BACK OF THIS SHEET. Do not ask anyone to explain any problem to you. Read the problem carefully and interpret its meaning. 1.

[9 points] For each of the following, choose the best answer; give the letter. (i) Which reacts faster with NaI in acetone: (a) 2-bromo-1,1-dimethylcyclopentane or (b) trans-1-bromo-3-methylcyclopentane? (ii) Which reaction with NaSH is slower: (a) (R)-2-bromopentane in DMSO or (b) (R)-2-bromopentane in ethanol? (iii) Which substrate reacts faster via an SN1 mechanism: (a) (R)-2-iodo-3-methylbutane or (b) 2-iodo-2,3-dimethylbutane ?

2.

1i)

2a)

[6 points] For each part (a-b) shown to the right, supply a structural formula for the major organic product(s) when the product(s) is(are) not given; if no reaction occurs, write N.R. IMPORTANT: If the major product is a mixture of stereoisomers (such as a mixture of enantiomers or a mixture of diastereomers), give a structural formula for each of the stereoisomers in the mixture. ALSO, write equal if equal amounts of stereoisomers are formed or unequal if unequal amounts of stereoisomers are formed. Provide the following when a product is given. If an organic reactant is missing, supply a structural formula; if an inorganic reactant (reagent) or catalyst is missing, simply give a formula. If heat and/or light is needed, be sure to indicate it appropriately if these conditions are missing. If more than one reaction step is needed, be sure to put 1. … and 2. … (etc.) as needed. Give the best possible answers. Be sure to show stereoisomers properly when necessary.

1ii)

1iii)

2b)

CHM 2210 Mar 23, 2017 PRINTED NAME: __________________________________________________________ Rec. Sec. No. 14, 17 & 18 Quiz 4C BlackBoard Login ____________________ SIGNED NAME: ___________________________________________________________ To earn full credit, provide all the information requested above. Clearly give your answers in the spaces provided. ***DO NOT WRITE ANYTHING ON THE BACK OF THIS SHEET. Do not ask anyone to explain any problem to you. Read the problem carefully and interpret its meaning. 1.

[9 points] For each of the following, choose the best answer; give the letter. (i) Which reacts faster with sodium cyanide in dimethyl sulfoxide: (a) 1-bromopentane or (b) pentyl p-toluenesulfonate? (ii) Which substrate reacts faster via an SN2 mechanism: (a) cis-1-chloro-4-methylcyclohexane or (b) cis-1-(chloromethyl)-4-methylcyclohexane? (iii) Which type of solvent is N,N-dimethylformamide best described as: (a) nonpolar; (b) polar protic; or (c) polar aprotic ?

2.

1i)

2a)

[6 points] For each part (a-b) shown to the right, supply a structural formula for the major organic product(s) when the product(s) is(are) not given; if no reaction occurs, write N.R. IMPORTANT: If the major product is a mixture of stereoisomers (such as a mixture of enantiomers or a mixture of diastereomers), give a structural formula for each of the stereoisomers in the mixture. ALSO, write equal if equal amounts of stereoisomers are formed or unequal if unequal amounts of stereoisomers are formed. Provide the following when a product is given. If an organic reactant is missing, supply a structural formula; if an inorganic reactant (reagent) or catalyst is missing, simply give a formula. If heat and/or light is needed, be sure to indicate it appropriately if these conditions are missing. If more than one reaction step is needed, be sure to put 1. … and 2. … (etc.) as needed. Give the best possible answers. Be sure to show stereoisomers properly when necessary.

1ii)

1iii)

2b)

CHM 2210 Mar 23, 2017 PRINTED NAME: __________________________________________________________ Rec. Sec. No. 19 Quiz 4D BlackBoard Login ____________________ SIGNED NAME: ___________________________________________________________ To earn full credit, provide all the information requested above. Clearly give your answers in the spaces provided. ***DO NOT WRITE ANYTHING ON THE BACK OF THIS SHEET. Do not ask anyone to explain any problem to you. Read the problem carefully and interpret its meaning. 1.

[9 points] For each of the following, choose the best answer; give the letter. (i) Does1-bromopentane undergo nucleophilic substitution faster (a) with 1 eq. NaOH in H2O solvent or (b) in only H2O solvent? (ii) Which substrate reacts faster via an SN2 mechanism with 1 eq. of NaI in acetone: (a) 1-bromo-1-methylcyclohexane or (b) cis-1-chloro-4-methylcyclohexane? (iii) Which type of solvent is tetrachloromethane best described as: (a) nonpolar; (b) polar protic; or (c) polar aprotic ?

2.

1i)

2a)

[6 points] For each part (a-b) shown to the right, supply a structural formula for the major organic product(s) when the product(s) is(are) not given; if no reaction occurs, write N.R. IMPORTANT: If the major product is a mixture of stereoisomers (such as a mixture of enantiomers or a mixture of diastereomers), give a structural formula for each of the stereoisomers in the mixture. ALSO, write equal if equal amounts of stereoisomers are formed or unequal if unequal amounts of stereoisomers are formed. Provide the following when a product is given. If an organic reactant is missing, supply a structural formula; if an inorganic reactant (reagent) or catalyst is missing, simply give a formula. If heat and/or light is needed, be sure to indicate it appropriately if these conditions are missing. If more than one reaction step is needed, be sure to put 1. … and 2. … (etc.) as needed. Give the best possible answers. Be sure to show stereoisomers properly when necessary.

1ii)

1iii)

2b)

CHM 2210 Mar 23, 2017 PRINTED NAME: __________________________________________________________ Rec. Sec. No. 20 Quiz 4E BlackBoard Login ____________________ SIGNED NAME: ___________________________________________________________ To earn full credit, provide all the information requested above. Clearly give your answers in the spaces provided. ***DO NOT WRITE ANYTHING ON THE BACK OF THIS SHEET. Do not ask anyone to explain any problem to you. Read the problem carefully and interpret its meaning. 1.

[9 points] For each of the following, choose the best answer; give the letter. (i) Does 2-bromo-2-methylbutane undergo nucleophilic substitution faster (a) with 1 eq. NaOH in H2O solvent or (b) in only H2O solvent? (ii) Which substrate reacts faster via an SN2 mechanism with 1 eq. of NaI in acetone: (a) cis-1-bromo-4-methylcyclohexane or (b) cis-1-chloro-4-methylcyclohexane? (iii) Which type of solvent is formic acid best described as: (a) nonpolar; (b) polar protic; or (c) polar aprotic ?

2.

1i)

2a)

[6 points] For each part (a-b) shown to the right, supply a structural formula for the major organic product(s) when the product(s) is(are) not given; if no reaction occurs, write N.R. IMPORTANT: If the major product is a mixture of stereoisomers (such as a mixture of enantiomers or a mixture of diastereomers), give a structural formula for each of the stereoisomers in the mixture. ALSO, write equal if equal amounts of stereoisomers are formed or unequal if unequal amounts of stereoisomers are formed. Provide the following when a product is given. If an organic reactant is missing, supply a structural formula; if an inorganic reactant (reagent) or catalyst is missing, simply give a formula. If heat and/or light is needed, be sure to indicate it appropriately if these conditions are missing. If more than one reaction step is needed, be sure to put 1. … and 2. … (etc.) as needed. Give the best possible answers. Be sure to show stereoisomers properly when necessary.

1ii)

1iii)

2b)...