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14. Which of the following transition structures r rresents an SN2 event? ep CH3 8- Br...
ndyla S Chapter 7 (Snl-Sn2-E1-E2) Revie w +Problems 1°Leaving group (example): Br React with the following...
ndyla S Chapter 7 (Snl-Sn2-E1-E2) Revie w +Problems 1°Leaving group (example): Br React with the following reagents (Strong base /strong nucleophile) B) I, NC, Na (Strong nucleophile/ weak base) C) H (NaH or Ca) tBuO/tBuOH (Strong base/non- nucleophile) D) H:0, ROH, RCO2H Weak nucleophile/ very weak base- even acidie "Solvolysis" - type reactions P 2010 2° Leaving group (example): (sometimes "hindered") Ri React with the following reagents (Strong base / strong nucleophile) B) I, NC. N (Strong nucleophile/ weak base)...
2. (1.5 pts) Label the following reagents as Good or Poor Nucleophiles AND as Strong or Weak Base...
2. (1.5 pts) Label the following reagents as Good or Poor Nucleophiles AND as Strong or Weak Bases. OK Na SH 3. (1.5 pt) Predict the productts) of the following reactions, if there are multiple products indicate which, if any, is the major product. Be sure to clearly mark the stereochemistry of chiral carbon atoms and draw multiple products if there is more than one stereoisomer that forms. HCI MeOH H2SO H2 Pd/BaSO4 quinoline 4. (3 pt) For the following...
7) Give the mechanism including the transition state. сн.ct çı SN2 НН 8) Give the mechanism....
7) Give the mechanism including the transition state. сн.ct çı SN2 НН 8) Give the mechanism. CH1 보 SN1 CHCH,CH-C CH. но H Br 9) Give the mechanism of the reaction shown below. CH CI E1 CH,OH 10) When 1-bromo-2,2-dimethylcyclopentane is heated in ethanol, one of the products which results is shown below. Provide a detailed, stepwise mechanism for the production of this compound, and give the name of the mechanism by which it is produced. CH3 CH3
Tulung ate n illud aludke place in a single step. In the Sn2 reaction, the nucleophile...
Tulung ate n illud aludke place in a single step. In the Sn2 reaction, the nucleophile attacks the a-carbon from the backside and displaces the leaving group with an inversion of configuration occurring at the carbon. In the E2 elimination reaction, strong base removes an acidic hydrogen from the B-carbon and an alkene is formed as the leaving group is expelled from the a-carbon. This elimination follows Zaitsey's rule whereby the more substituted alkene is generally formed. In E2 elimination,...
39. What is the major product obtained from the following reaction? Br CH3 (CH3)2CO (CH3)2COH Ol-Bu...
39. What is the major product obtained from the following reaction? Br CH3 (CH3)2CO (CH3)2COH Ol-Bu CH3 CH3 Ol-Bu CH3 CH3 11 III IV A) III B) I C II D IV 40. What must be the starting material of the following reaction? NaOH A B. ОН ОН a. Hori D. ia ОН ОН 41. Which reaction mechanisms are most likely to occur when (R)-2-iodohexane is heated with KOH in acetone? CH, H.C A) Snl and Sn2 B) E1 and...
When determining which mechanism (E1 or E2) occurs, the following process is helpful: 1) Determine the...
When determining which mechanism (E1 or E2) occurs, the following process is helpful: 1) Determine the substitution (methyl, 1º, 2º, or 3“) of the alkyl halide 2) Determine the strength of the nucleophile Please fill out the following table, indicating the category of reaction (E1 or E2) that will occur in each set of alkyl halides and nucleophiles. If no reaction occurs, write 'NR: Alkyl Halide Strong Base Weak Base Methyl 1° 20 3° For each of the following reactions,...
If you desire to perform a "clean" E2 reaction, which of the following factors helps avoid...
If you desire to perform a "clean" E2 reaction, which of the following factors helps avoid competition with SN2 mechanism? a. use of a polar solvent b. use of a hindered bulky base c. use of a good nucleophile d. use of a good leaving group Alcohol dehydration is mechanistically an: a. SN2 reaction b. E2 reaction c. E1 reaction d. SN1 reaction
1. What substitution mechanism will the following reaction likely proceed through? (1pt) CH3 HU. : N=C:...
1. What substitution mechanism will the following reaction likely proceed through? (1pt) CH3 HU. : N=C: +3C-Br - NC-C WH + Br HT 2. Label the componetns of the above reation as: Nucleophile, electrophile, leaving group (3pt) 3. Assign R and S configuration to the following reactant and products (2pt) NaOH HO + HO-COCH3 H.COwc-OH + HO-6 H2COCCI H H 4. What ratio should the two above products be formed in and what is their stereochemical relationship? (2pt) 5. Predict...
1. Which of the following structures is/are a secondary alkyl halide? (a) I and II (b)...
1. Which of the following structures is/are a secondary alkyl
halide? (a) I and II (b) II and V (c) I, II and V (d) IV only (e)
I, II and III 2. Which of the following is/are aprotic solvent(s)?
Choose all correct answers. (a) (b) (c) (d) (e) (f) 3. Which of the
following carbocations, if formed, is (are) likely to undergo
rearrangement through a hydride shift? (a) I (b) II (c) III (d) I
and II (e) II...
Regioselectivity of E1 and E2 Reactions 3. The reaction between a 1,2-dimethylcyclohexanol and concentrated strong acid...
Regioselectivity of E1 and E2 Reactions 3. The reaction between a 1,2-dimethylcyclohexanol and concentrated strong acid results in an E1 reaction. Show the first step in this reaction (consider that the acid catalyst can protonate the OH group which eventually can form H2O that can act as a good leaving group). а. сн, OH conc.H2SO4 CH3 b. What is the geometry at the reaction center of the intermediate? Show the final step and all possible alkene products с. State the...
ndyla S Chapter 7 (Snl-Sn2-E1-E2) Revie w +Problems 1°Leaving group (example): Br React with the following reagents (Strong base /strong nucleophile) B) I, NC, Na (Strong nucleophile/ weak base) C) H (NaH or Ca) tBuO/tBuOH (Strong base/non- nucleophile) D) H:0, ROH, RCO2H Weak nucleophile/ very weak base- even acidie "Solvolysis" - type reactions P 2010 2° Leaving group (example): (sometimes "hindered") Ri React with the following reagents (Strong base / strong nucleophile) B) I, NC. N (Strong nucleophile/ weak base)...
2. (1.5 pts) Label the following reagents as Good or Poor Nucleophiles AND as Strong or Weak Bases. OK Na SH 3. (1.5 pt) Predict the productts) of the following reactions, if there are multiple products indicate which, if any, is the major product. Be sure to clearly mark the stereochemistry of chiral carbon atoms and draw multiple products if there is more than one stereoisomer that forms. HCI MeOH H2SO H2 Pd/BaSO4 quinoline 4. (3 pt) For the following...
7) Give the mechanism including the transition state. сн.ct çı SN2 НН 8) Give the mechanism. CH1 보 SN1 CHCH,CH-C CH. но H Br 9) Give the mechanism of the reaction shown below. CH CI E1 CH,OH 10) When 1-bromo-2,2-dimethylcyclopentane is heated in ethanol, one of the products which results is shown below. Provide a detailed, stepwise mechanism for the production of this compound, and give the name of the mechanism by which it is produced. CH3 CH3
Tulung ate n illud aludke place in a single step. In the Sn2 reaction, the nucleophile attacks the a-carbon from the backside and displaces the leaving group with an inversion of configuration occurring at the carbon. In the E2 elimination reaction, strong base removes an acidic hydrogen from the B-carbon and an alkene is formed as the leaving group is expelled from the a-carbon. This elimination follows Zaitsey's rule whereby the more substituted alkene is generally formed. In E2 elimination,...
39. What is the major product obtained from the following reaction? Br CH3 (CH3)2CO (CH3)2COH Ol-Bu CH3 CH3 Ol-Bu CH3 CH3 11 III IV A) III B) I C II D IV 40. What must be the starting material of the following reaction? NaOH A B. ОН ОН a. Hori D. ia ОН ОН 41. Which reaction mechanisms are most likely to occur when (R)-2-iodohexane is heated with KOH in acetone? CH, H.C A) Snl and Sn2 B) E1 and...
When determining which mechanism (E1 or E2) occurs, the following process is helpful: 1) Determine the substitution (methyl, 1º, 2º, or 3“) of the alkyl halide 2) Determine the strength of the nucleophile Please fill out the following table, indicating the category of reaction (E1 or E2) that will occur in each set of alkyl halides and nucleophiles. If no reaction occurs, write 'NR: Alkyl Halide Strong Base Weak Base Methyl 1° 20 3° For each of the following reactions,...
1. What substitution mechanism will the following reaction likely proceed through? (1pt) CH3 HU. : N=C: +3C-Br - NC-C WH + Br HT 2. Label the componetns of the above reation as: Nucleophile, electrophile, leaving group (3pt) 3. Assign R and S configuration to the following reactant and products (2pt) NaOH HO + HO-COCH3 H.COwc-OH + HO-6 H2COCCI H H 4. What ratio should the two above products be formed in and what is their stereochemical relationship? (2pt) 5. Predict...
1. Which of the following structures is/are a secondary alkyl
halide? (a) I and II (b) II and V (c) I, II and V (d) IV only (e)
I, II and III 2. Which of the following is/are aprotic solvent(s)?
Choose all correct answers. (a) (b) (c) (d) (e) (f) 3. Which of the
following carbocations, if formed, is (are) likely to undergo
rearrangement through a hydride shift? (a) I (b) II (c) III (d) I
and II (e) II...
Regioselectivity of E1 and E2 Reactions 3. The reaction between a 1,2-dimethylcyclohexanol and concentrated strong acid results in an E1 reaction. Show the first step in this reaction (consider that the acid catalyst can protonate the OH group which eventually can form H2O that can act as a good leaving group). а. сн, OH conc.H2SO4 CH3 b. What is the geometry at the reaction center of the intermediate? Show the final step and all possible alkene products с. State the...
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