Which of the following alkyl halides would undergo an SN2 reaction most readily? a....
Question:
Which of the following alkyl halides would undergo an SN2 reaction most readily?
a. 1-bromo-3-ethylcyclohexane
b. 1-bromo-1-ethylcyclohexane
c. 1-bromo-2,2-dimethylhexane
d. 1-bromo-3-ethylhexane
Primary, secondary, and tertiary halides:
Attachment of halogen to a carbon joined to another single carbon, two carbons, and three carbons respectively forms primary, secondary, and tertiary halides. Used for classifying the types of halogens. Useful in predicting the reactivity of haloalkanes and haloarenes.
Answer and Explanation: 1
Become a Study.com member to unlock this answer! Create your account
View this answerBimolecular nucleophilic substitution reaction
This type of reactions involves a single step. It is a concerted reaction where cleavage and...
See full answer below.
Ask a question
Our experts can answer your tough homework and study questions.
Ask a question Ask a questionSearch Answers
Learn more about this topic:
Get access to this video and our entire Q&A library
Nucleophilic Substitution in Haloalkanes
from
Chapter 11 / Lesson 2
25K
Learn about nucleophilic substitution. Explore two types of nucleophilic substitution reactions: study SN1 and SN2 reaction mechanisms and corresponding examples.
Related to this Question
- Which alkyl halides are expected to undergo Friedel- Crafts reaction with rearrangement and which without? Explain. (a) CH_3CH_2Cl (b) CH_3CH_2CH(Cl)CH_3 (c) CH_3CH_2CH_2Cl (d) (CH_3)_3CCH_2Cl (e) Chlorocyclohexane
- Which of the following alkyl halides would undergo SN2 reaction most rapidly? (A) CH3CH2-Br (B) CH3CH2- Cl (C) CH3CH2-I (D) CH3CH2-F (E) they react at the same rate
- What alkyl halides are formed when the given ether is treated with HBr?
- What alkyl halides are formed when the given below ether is treated with HBr?
- In what type of reaction is an alkane converted to an alkyl halide?
- Which alkyl halide would you expect to undergo an SN2 reaction most slowly? a. 1-bromo-4-methylpentane b. 1-bromo-3-methylpentane c. 1-bromo-2-methylpentane d. 1-bromo-2,2-dimethylbutane
- Which of the following halides will not work as an electrophile in a Friedel-Crafts alkylation reaction?
- Which halides are unreactive in a Friedel-Crafts alkylation reaction?
- What happens when alkyl halides are reacted with KCN and AgCN?
- Which of the following halides cannot be used for Friedel-Crafts alkylation reaction? \\ Select one: \\ a bromobenzene b. vinylchloride c. 2-chloropropane d. chloroethane e. both A and B
- What alkyl halide forms the following alkene as the only product in an elimination reaction?
- What alkyl halide might the following alkene below have been made from?
- Which of the following halides cannot be used for a Friedel-Crafts alkylation reaction? A. bromobenzene B. vinyl chloride C. 2-chloropropane D. chloroethane E. both A and B
- Which alkyl halide in the mentioned pair will react faster in an SN2 reaction with OH-? CH3Cl or (CH3)3CCl
- What alkyl halides are formed when the below ether is treated with HBr?
- Identify the alkyl halide that reacts the fastest in a S_N2 reaction. A) 2-chloro-2-methylpropane. B) 1-chlorobutane. C) 2-chlorobutane. D) chloromethane.
- What alkyl halide forms each of the following alkenes as the only product in an elimination reaction?
- Alkyl halides react with hydrosulfide ion (HS^-) to give a product whose stereochemistry is inverted from that of the reactant. Draw the reaction of (S)-2-bromobutane with HS^- ion to yield 2-butanethiol, CH_3CH_2CH(SH)CH_3. Is the
- Identify the alkyl halide that reacts the fastest in an S_N1 reaction. A) 2-chloro-2-methylpropane. B) 2-chlorobutane. C) 1-chlorobutane. D) chloromethane.
- What alkene would you start with to prepare the given alkyl halide?
- Which alkene should be used to synthesize the following alkyl bromide?
- Which alkyl halide in the given pair will react faster in an SN2 reaction with OH-? Bromobenzene or benzyl bromide, C6H5CH2Br
- What alkyl halides are needed to prepare the given ketone using the acetoacetic ester synthesis?
- From what alkyl bromide was the following alkyl acetate made by SN2 reactions? Write the reaction, showing all stereochemistry.
- What carboxylic acid is obtained from the malonic ester synthesis when the alkyl halide is propyl bromide?
- What alkyl halides are needed to prepare the given carboxylic acid using the malonic ester synthesis?
- What alkyl halides are needed to prepare the given carboxylic acid by the malonic ester synthesis?
- What alkene can be used to prepare the given alkyl halide or dihalide as the exclusive or major product of an addition reaction?
- Which benzylic halide reacts faster in an S_N1 reaction? Explain.
- 1. Identify the following from the reaction (2S) 2-Bromohexane + NaCN /CH_3 CN rightarrow a) Leaving group b) solvent c) What type of alkyl halide is it? d) What is the nucleophile? 2. Draw the
- What alkene would you start with to prepare the depicted alkyl halide?
- What alkyl halide and nucleophile are needed to prepare the given compound?
- What alkyl halides are needed to prepare the following carboxylic acid by the malonic ester synthesis?
- Which of the following S_(N)2 reactions would you expect to be faster? Reaction of I^- with (CH_3)_2CHCH_2Cl or with H_2C=CHCl?
- What alkyl halide and nucleophile would be used to prepare the below-mentioned product by an SN2 mechanism?
- What alkyl halide and nucleophile would be used to prepare the below-mentioned product by an SN1 mechanism?
- 29) Which of the following alkyl halides can produce only a single alkene product from when treated with sodium methoxide? A) 2-chloro-2-methylpentane B) 3-chloro-3-ethylpentane C) 3-chloro-2-methylpentane D) 2-chloro-4-methylpentane E) 2-chloro ...
- Identify the halide(s) that react in a SN1 reaction. Check all that apply. a.1-bromo-2-butene b. 2-bromo-2-phenylpropane c.bromobenzene d.1-bromo-1-butene e.benzyl bromide
- Which compound in the depicted set is more reactive in nucleophilic acyl substitution reaction? CH3CO2CH3 or CH3CO2COCH3
- Which one is the best nucleophile for a S_N2 reaction with propel bromide? A. NaCI B. KCN C. H_2O D. HI a. A b. B c. C d. D
- How can an alkyl halide be converted into an alkene?
- Which reactant in the following pairs is more nucleophilic? I^- or Cl^-
- Which alkene should be used to synthesize the following alkyl bromide? (There is more than one correct answer.)
- Which alkyl halide would you expect to react more rapidly by an Sn2 mechanism? Explain your answer. [{Image src='alkyl2535000792615083478.jpg' alt='alkyl' caption=''}]
- Alkenes cannot undergo which type of reaction? a)Addition b)Oxidation c)Hydration d)Polymerization e)Dehydration
- What is the likely mechanism of nucleophilic substitution for the given alkyl halide?
- What is the likely mechanism of nucleophilic substitution for the following alkyl halide?
- Identify the alkyl halide that reacts the fastest in an S_N1 reaction. A) 2-bromopropane. B) 2-iodopropane. C) 2-fluoropropane. D) 2-chloropropane.
- Which of the following compounds shown below will be the most likely product formed from an Alkyl shift during the solvolysis of 1-iodo-2,2-dimethylpentane in CH_3OH?
- What amine would react with what acid chloride to give the depicted amide product? (CH3)2CHCH2CONHCH3
- Which one of the following reactions is most likely to give a polysubstituted product A) Friedel-Crafts alkylation B) Friedel-Crafts acylation C) Nitration D) Sulfonation E) Halogenation
- If the reaction of an alcohol with PBr3 follows an SN2 mechanism, what is the stereochemistry of the alkyl bromide formed from (R)-butan-2-ol?
- What alkyl halide is needed to prepare the given compound by a malonic ester synthesis?
- What alkene would you start with to prepare the specified alkyl halide? 1-Iodo-1-isopropylcyclohexane
- What is the likely mechanism of nucleophilic substitution for shown alkyl halide?
- Which carbonyl compounds do not undergo an aldol reaction when treated with -OH in H2O?
- Which one of the following reaction is most likely to give a polysubstituted product? A) Friedel-Crafts alkylation B) Friedel-Craft acylation C) Nitration D) Sulfonation E) Halogenation
- Which of the following compounds could be subjected to a haloform reaction? a. 4-heptanone b. 3-hexanone c. 2-hexanone d. cyclohexanone e. methyl acetate
- Nitriles are prepared by reactions of unhindered methyl and 1 alkyl halides with -CN.
- Reaction of (S)-3-methyl-2-pentanone with methylmagnesium bromide followed by acidification yields 2,3-dimethyl-2-pentanol. What is the stereochemistry of the product? Is the product optically active?
- Which one of the following compounds will be most reactive towards bromination reaction: A) Nitrobenzene B) Anisole C) Acetanilide D)Benzene E)Benzaldehyde
- 1) Please identify the following from the reaction: a) Leaving group b) solvent c) What type of alkyl halide is it? d) What is the nucleophile? 2) Please draw the structure of (2S) 2-Bromohexane and
- a. What is an SN1 reaction? Explain the mechanism for this reaction. b. What types of halides will undergo SN1 mechanisms and what type will not? Why? c. What other experimental conditions promote SN1 mechanism?
- What alkyl halides are needed to prepare the below carboxylic acid by the malonic ester synthesis?
- Find the alkyl halides that are needed to prepare the given carboxylic acid using the malonic ester synthesis?
- What product is formed when benzene is treated with the given organic halide in the presence of AlCl3?
- What product is formed when benzene is treated with the following organic halide in the presence of AlCl3?
- Which, if any, of the following compounds can be prepared by a malonic ester synthesis? Show the alkyl halide you would use in each case. (a) Ethyl pentanoate (b) Ethyl 3-methylbutanoate (c) Ethyl 2-methylbutanoate (d) Ethyl 2,2-dimethylpropanoate
- Which reactant in the following pairs is more nucleophilic? BF_3 or F^-
- Which compound in the given set is more reactive in nucleophilic acyl substitution reaction? CH3COCl or CH3CO2CH3
- What alkenes are formed from the given alkyl halide by an E2 reaction? Use the Zaitsev rule to predict the major product.
- What alkenes are formed from each alkyl halide by an E1 reaction? Use the Zaitsev rule to predict the major product. a. b.
- Describe a sequence of reactions by which trans 2 pentene can be straight forwardly prepared from propyne.
- Which compound in the mentioned set is more reactive in nucleophilic acyl substitution reaction? (CH3)2CHCONH2 or CH3CH2CO2CH3
- What is the likely mechanism of nucleophilic substitution for the below alkyl halide?
- What is the identity of the ppt formed during the SN1 reactions carried out with various alkyl halides and AgNO_3/ethanol?
- What stereoisomers are obtained when (s)-3-methyl-1-pentene reacts with Cl_2?
- Which of the following statements explains why aryl halides and vinyl halides do not undergo nucleophilic substitution by either the SN1 or SN2 mechanism? a. They don't undergo SN1 reactions because a higher percent s-character makes the bond longer and s
- What product is formed when 1-bromopropane reacts with each of the following nucleophile a. HO^- b. NH_3 c. CH_3SH d. HS^- e. CH_3O^- f. CH_3NH_2
- What alkyl halide is needed to prepare the given ketone below using the acetoacetic ester synthesis?
- What alkyl halide is needed to prepare the given ketone using the acetoacetic ester synthesis?
- Which substance in each of the following pairs is more reactive as a nucleophile? Explain. (a) (CH_3)_2N^- or (CH_3)_2NH. (b) (CH_3)_3B or (CH_3)_3N. (c) H_2O or H_2S.
- Which reagents are appropriate for the Friedel-Crafts alkylation reaction? A. Br2/FeBr3 B. AlCl3/CH3CH2Cl C. H2SO4/H2O D. Cl2/DCM
- What would be the product of this halogenation reaction? CH_3 - CH_2 - CH_3 + Br_2 to
- What product is formed when benzene is treated with the below organic halide in the presence of AlCl3?
- Which compound would react faster under S_{N2} conditions? allylic chloride or n-butyl chloride
- Which reactant in the following pairs is more nucleophilic? -^C equiv N or -^OCH_3
- Which of the following S_(N)2 reactions would you expect to be faster? Reaction of CN^- (cyanide ion) with CH_3CH(Br)CH_3 or with CH_3CH_2CH_2Br
- What is the reactive intermediate in the reaction of 1,3-butadiene with HBr resulting in 1,2-addition? a. cyclic bromonium carbon. b. allylic cation c. allylic radical d. dienophile.
- What type of reactive intermediate is formed in the reaction of an alkene with HBr to give a bromoalkane? (a) carbocation (b) carbanion (c) radical (d) cyclic bromonium ion
- Which of the following compounds cannot be a reactant in an addition reaction involving the addition of chlorine? \\ A. 1-chloro-4-decene B. 2-pentene C. propene D. 3-methyl-2-nonene E. 2-methylbutane
- Which compound in the specified set is more reactive in nucleophilic acyl substitution reaction? CH3CO2CH3 or CH3CHO
- What amine would react with what acid chloride to give the mentioned amide product? CH3CH2CONH2
- a. What mechanism do you believe will be favored with NaI in acetone? b. What order of reactivity do you predict will be observed when each of the alkyl halides is reacted with NaI in acetone? c.Lis
- Ignoring double-bond stereochemistry, what product would you expect from the elimination reaction of the following alkyl halide below? Which product will be the major product in the below case?
- How do you know which electrophilic carbon would be attacked by a nucleophile in a bimolecular reaction?
- Find the alkyl halide and nucleophile needed to prepare the given compound.
- What atoms are oxidized and reduced in the reaction of HBr and H2O2 to form Br2 and H2O? If Bromide is a better nucleophile toward the intermediate bromonium ion than ethanol, what product would be obtained if ethanol did carry out the nucleophilic attack
Explore our homework questions and answers library
Browse
by subject