Write A if the given statement refers to SN1 reaction, otherwise write B for SN2 mechanism 1. Single step reaction 2. Stereochemistry proceeds in both inversion and retention 3. Tertiary alkyl halides works best 4. Protic solvents favours stability of the intermediates and leaving group 5. Hardly affected by the nature of the nucleophile

Write A if the given statement refers to SN1 reaction, otherwise write B for SN2 mechanism 1. Single step reaction 2. Stereochemistry proceeds in both inversion and retention 3. Tertiary alkyl halides works best 4. Protic solvents favours stability of the intermediates and leaving group 5. Hardly affected by the nature of the nucleophile

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter13: Substitution

Section: Chapter Questions

Problem 59CTQ

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Circle the electrophilic and nucleophilic atoms in each substitution reaction below. Provide the neutral organic product; where a stereocenter is created, use a wavy bond to indicate a mixture of configurations or wedges/dashes for stereospecific reactions. Also, provide the dominant reaction mechanism (SN2 or SN1) somewhere in each box. E. 文 HCI HO. OH F. NANHTS H3C, DMF
1. Which of the following is the strongest nucleophile? Refer to the diagram below with an MeOH, MeSH, etc. 2. Which of the following is true about the stereochemistry of SN1 reaction?a.retention of configuration at the electrophilic centerb.50:50 mixture of retention and inversion of configuration at the electrophilic centerc.inversion of configuration at the electrophilic centerd. slightly more inversion than retention at the electrophilic center
A reaction flask contains 2-bromopentane in an ethanolic solution of sodium ethoxide at room temperature and result in the formation of two olefnic products. What is responsible for the formation of major and minor products. A. Different activated complex involved in the mechanism. B. Bimolecular nucleophilic substitution reaction. C. Bimolecular elimination reaction D. The presence of sodium ethoxide. E. The hybridization nature of secondary carbocation
2. Draw the structures and explain why CH3CH₂O and CH3CO₂ are good nucleophiles but CH3SO3, water, and alcohols (R-OH) are poor nucleophiles. Propose a 'cutoff' for the amount of negative charge needed to be a good nucleophile. CH3CH₂O CH3CO₂ CH3SO3 H₂O CH₂OH
4. Circle the electrophilic and nucleophilic atoms in each substitution reaction below. Provide the neutral organic product; where a stereocenter is created, use a wavy bond to indicate a mixture of configurations or wedges/dashes for stereospecific reactions. Also, provide the dominant reaction mechanism (Sn2 or SN1) somewhere in each box. A. Br NaSEt DMF В. ELOH C. .SO2NHNA Cl + D. NaH Br- HO, DMF
The boiling point of which compound is HIGHER than CH3CH2CH2CH2OH? a. CH3CH2CH2CHO O b. CH3CH20CH2CH3 Oc. isobutyl alcohol O d. CH3CH2COOH The transition state structure below is most likely to occur in the reaction of what nucleophile and substrate? H CH3 CH30-…..C....-Br CH;0-… ČE Select one: O a. Methoxide with 1-bromopropane b. Methanol with 1-bromopropane O c. Methanol with 2-bromopropane O d. Methoxide with 2-bromopropane
From the Hammet equation data, it was observed that the nucleophilic substitution reaction of benzyl bromide and benzyl bromide with substituents at the ortho- and para-positions have shown a negative p value. Which of the following statements is/are True? A. The halide leaves before the nucleophile attacks the electrophilic site B. A concerted type of reaction has occurred. C. A decrease in electron density has occurred at the transition state D. An increase in electron density has occurred at the transition state E. A and C
4. Complete the phrases with one or more of the following terms: SNI, SN2, E1, E2. a) The reaction takes place in two or more steps. b) The reaction goes through a carbocation. c) The rate determining step has two reactants. d) The rate is independent of the concentration of nucleophile or base. e) Zaitsev's rule is often applicable to the products..
21. Which of the following solvents is protic? A. acetone B. propyl chloride C. ethanal D. ethanol E. diethyl ether 22. Which of the following statements is generally true for SN1 reactions? A) Complete inversion of configuration occurs. B) These are favored by nonpolar solvents. C)These reactions are favored by polar solvents. D) Reaction rates depend only on the concentration of the nucleophile. E) The mechanism is a one-step back attack. 23. Which of the alkyl chlorides listed below undergoes dehydrohalogenation in the presence of a strong base to give 2-pentene as the only alkene product? A) 1-chloropentane B) 2-chloropentane C) 3-chloropentane D) 1-chloro-2-methylbutane E) 1-chloro-3-methylbutane
20. a. Label the reactive features, highlight the most reactive one, then highlight what it needs. Also, state if the reaction will start to create a carbocation, carbon radical, or carbanion, or will cause loss of aromatic character. If a carbocation, carbon radical, or carbanion starts to develop, label where that will occur. o-cresol + 2-methylpropanoyl chloride + AICI3 b. Use mechanism arrows to illustrate the reaction that occurs. c. If applicable, use stabilization resources to deal with the carbocation, carbon radical, or carbanion that starts to develop during the reaction, and draw the structure of any resonance-stabilized intermediate. d. Continue labeling and diagramming the reaction until you find the major stable product(s). e. Finally, state the stereochemistry of the major product(s) and use either Fisher projection or perspective formula representations to illustrate that stereochemistry.
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10. Explain the reaction shown below. Include the following pieces in your explanation. Identify the electrophile and the nucleophile. Draw a curved arrow mechanism for this reaction. (Assume an acidic work-up). Explain the electron flow. Indicate any regiochemical or stereochemical preferences. one b. c. d. LIAIH4 OH one