The chemistry of deuterium is nearly identical to that of hydrogen. One area of difference is that C-D bonds are about 1.2 kcal/mol stronger than C-H bonds. As a result, reaction rates tend to be slower if a C-D (as opposed to C-H) bond is broken in a rate-limiting step. This important fact can lead to great mechanistic insight and is called the kinetic isotope effect.
a) Propose a mechanism to explain each product in the following reaction.
b) When the following compound reacts under the same conditions, the rate of the substitution reaction is unchanged, but the rate of the elimination reaction is 7 times slower. Explain.
c) When the following compound is treated with sodium methoxide in methanol, two elimination products are possible. Explain why the deuterated product predominates by about 7:1.
Homework Answers
c) when aldol reaction is carried out in D2O, deuterium may be
incorporated in acetone but not in aldehyde because in case of -CHO
second step which include attack of carbanion on carbonyl is fast.
So carbanion does not have time to interact with D2O which makes
deuterium to predominate the reaction.
Add Answer to:
The chemistry of deuterium is nearly identical to that of
hydrogen. One area of difference is...
(16) 6. Deuterium is the isotope of hydrogen of mass number 2, with a proton and...
(16) 6. Deuterium is the isotope of hydrogen of mass number 2, with a proton and a neutron in its nucleus. It is often designated 2H, or D. We have seen that the chemistry of deuterium is nearly identical to the chemistry of hydrogen, except that the C-D bond is slightly (1.2 kcal/mole) stronger than the C-H bond. a) Propose (show) a mechanism to explain each product in the following reaction: CH2-CHCH CH CH CH3 CH3 CH CH3 KOH +...
For letters h & i : For each of the following reactions, predict the major mechanistic pathway (SN1/SN2/E1/E2...
For
letters h & i :
For each of the following reactions, predict the major
mechanistic pathway (SN1/SN2/E1/E2) and the major organic
products
1. (cont.) (h) НСОН CHB -CHBr HCOH - (0) CH,CH,CH,CH,Br- NH 2. For each of the following indicate which reaction will occur faster. Explain your reasoning. (No credit will be given for guesses) (a) The reaction of (CH),CBr with 0.001M aqueous NaOH or 0.10M aqueous NaOH (b) The reaction of 2-bromobutane with NaOH in DMSO or NaSH...
_1. An alkyl halide which might be expected to undergo rearrangement under Snl or E1 conditions...
_1. An alkyl halide which might be expected to undergo rearrangement under Snl or E1 conditions is: HZC Br CH3 A. 1 B. | F—CH,BH C. CH3-C-CH-CH, CHz CH3 D. CH3 CH3-C-CH2CH2-Br CH3 E. A Br 2. Your task is to convert 2-chloropentane into 1-pentene. Which reagents would you choose? a) NaOH/H20 b) KOH/CH3OH c) CH3ONa/CH3OH d) CH3CH2ONa/CH3CH2OH e) (CH3)3COK/(CH3)3COH 3. Circle the reaction below which is faster in polar protic solvents. OH,H,O A. CH,CH,CH,Br- CH,CH,CH,OH + Br or SH.RSH...
CH3 (4) 1. Which of the following alkyl halides would you expect to be most reactive...
CH3 (4) 1. Which of the following alkyl halides would you expect to be most reactive in a unimolecular reaction? a) C&H, CH, CH, CH, BY b) CH 1 CH CH Br C) CH11CCH, Br d) C6H CH2 CH CHỊ CHỊ CH3 CHỊ e) C&H, CCH Br CHE (4) 2. What would you expect to be the chief organic product(s) when tert-butyl bromide reacts with sodium acetylide, i.e., CH3 + - CH2-C-Br + Na :CECH — ? CH a) I...
b) CH, CH2 CH CH Br + SH — CHZ CH3 CH, CH, CH, Br + SH" — c) (polar protic solvents) CH, Br + (CH3)3N CH, Br + (CH3)3P...
b) CH, CH2 CH CH Br + SH — CHZ CH3 CH, CH, CH, Br + SH" — c) (polar protic solvents) CH, Br + (CH3)3N CH, Br + (CH3)3P - — d) CH, I + CN- - DMF CHZI + CNC CH3CH20H e) CH I + OH- - CHZI + CH, CO2- (6) 14. Place 1º, 2º, 3º and Methyl carbocations in order from least stable to most stable. What factor(s) account for the stability of the most stable...
1-24 need help really lost Proton Transfer: deprotonation D. 1) Add the appropriate curved arrows for...
1-24 need help really lost
Proton Transfer: deprotonation D. 1) Add the appropriate curved arrows for the following deprotonation step. Also add the other product notice how the Tema s can be converted to this by use of a strong base such as sodium a sodium ion (Na) is not drawn, in this case it is just a spectatorio PCW27 - Mechanistic steps - Part Name: Time spent 2) Label the above compounds with the appropriate name from the previous...
Please completely answer the questions, thank you! For the reactions below, 1. supply the reagents needed...
Please completely answer the questions, thank you!
For the reactions below, 1. supply the reagents needed to carry out the reaction, by writing them above the reaction arrow. 2. Use choices 1A through 11, 2A through 24, and 3A through 3X, above to answer the questions about reaction types and mechanistic details. 3. For the reactions in column 3, that require you to diagram the mechanism, diagram the mechanism. Column 1 Column 2 Column 3 Type of Reaction The Reason...
please answer all parts, thanks! 1. More substituted alkenes are more stable than less substituted alkenes....
please answer all parts, thanks!
1. More substituted alkenes are more stable than less substituted alkenes. Show the orbital overlap that helps to explain this observation. 2. Why is the heat of hydrogenation for an alkene exothermic? Analyze the bonds that are changing. AH = -30 kcal/mol Explain: + H2 3. Treating alkene "A" below with HBr can lead to a number of products. "A" SM + H-Br A bunch of products. For real, hella products. 3.A. Label the stereocenters...
How to properly solve these elimination and addition reactions Elimination and Addition reactions Purpose: Fi...
How to properly solve these elimination and addition
reactions
Elimination and Addition reactions Purpose: Figuring out the ways that molecules react is the province of the mechanistic chemist. By understanding the mechanisms of reactions, the chemist can manipulate the experimental variables to favor one product over another. This element of control is the province of the synthetic organic chemist. This Workshop continues to explore how we know how molecules react and how this knowledge leads to control of the products....
Help with questions 2, F on question 8a, and question 8b please. UUUU CHEM 2030, Sections...
Help with questions 2, F on question 8a, and question 8b
please.
UUUU CHEM 2030, Sections 3.5-3.9 Reactions and Mechanisms, Introduction College Tip: Please read and take notes on the chapter before coming to class. It reduces overall anxiety and other feelings of discomfort. Additionally, it increases feelings of understanding and helps you ask more 'in-depth' questions. Instructions. Please see previous handouts for repetitive instructions. Oa. Memorize all boldface words in the chapter and be able to use them in...
(16) 6. Deuterium is the isotope of hydrogen of mass number 2, with a proton and a neutron in its nucleus. It is often designated 2H, or D. We have seen that the chemistry of deuterium is nearly identical to the chemistry of hydrogen, except that the C-D bond is slightly (1.2 kcal/mole) stronger than the C-H bond. a) Propose (show) a mechanism to explain each product in the following reaction: CH2-CHCH CH CH CH3 CH3 CH CH3 KOH +...
For
letters h & i :
For each of the following reactions, predict the major
mechanistic pathway (SN1/SN2/E1/E2) and the major organic
products
1. (cont.) (h) НСОН CHB -CHBr HCOH - (0) CH,CH,CH,CH,Br- NH 2. For each of the following indicate which reaction will occur faster. Explain your reasoning. (No credit will be given for guesses) (a) The reaction of (CH),CBr with 0.001M aqueous NaOH or 0.10M aqueous NaOH (b) The reaction of 2-bromobutane with NaOH in DMSO or NaSH...
_1. An alkyl halide which might be expected to undergo rearrangement under Snl or E1 conditions is: HZC Br CH3 A. 1 B. | F—CH,BH C. CH3-C-CH-CH, CHz CH3 D. CH3 CH3-C-CH2CH2-Br CH3 E. A Br 2. Your task is to convert 2-chloropentane into 1-pentene. Which reagents would you choose? a) NaOH/H20 b) KOH/CH3OH c) CH3ONa/CH3OH d) CH3CH2ONa/CH3CH2OH e) (CH3)3COK/(CH3)3COH 3. Circle the reaction below which is faster in polar protic solvents. OH,H,O A. CH,CH,CH,Br- CH,CH,CH,OH + Br or SH.RSH...
CH3 (4) 1. Which of the following alkyl halides would you expect to be most reactive in a unimolecular reaction? a) C&H, CH, CH, CH, BY b) CH 1 CH CH Br C) CH11CCH, Br d) C6H CH2 CH CHỊ CHỊ CH3 CHỊ e) C&H, CCH Br CHE (4) 2. What would you expect to be the chief organic product(s) when tert-butyl bromide reacts with sodium acetylide, i.e., CH3 + - CH2-C-Br + Na :CECH — ? CH a) I...
b) CH, CH2 CH CH Br + SH — CHZ CH3 CH, CH, CH, Br + SH" — c) (polar protic solvents) CH, Br + (CH3)3N CH, Br + (CH3)3P - — d) CH, I + CN- - DMF CHZI + CNC CH3CH20H e) CH I + OH- - CHZI + CH, CO2- (6) 14. Place 1º, 2º, 3º and Methyl carbocations in order from least stable to most stable. What factor(s) account for the stability of the most stable...
1-24 need help really lost
Proton Transfer: deprotonation D. 1) Add the appropriate curved arrows for the following deprotonation step. Also add the other product notice how the Tema s can be converted to this by use of a strong base such as sodium a sodium ion (Na) is not drawn, in this case it is just a spectatorio PCW27 - Mechanistic steps - Part Name: Time spent 2) Label the above compounds with the appropriate name from the previous...
Please completely answer the questions, thank you!
For the reactions below, 1. supply the reagents needed to carry out the reaction, by writing them above the reaction arrow. 2. Use choices 1A through 11, 2A through 24, and 3A through 3X, above to answer the questions about reaction types and mechanistic details. 3. For the reactions in column 3, that require you to diagram the mechanism, diagram the mechanism. Column 1 Column 2 Column 3 Type of Reaction The Reason...
please answer all parts, thanks!
1. More substituted alkenes are more stable than less substituted alkenes. Show the orbital overlap that helps to explain this observation. 2. Why is the heat of hydrogenation for an alkene exothermic? Analyze the bonds that are changing. AH = -30 kcal/mol Explain: + H2 3. Treating alkene "A" below with HBr can lead to a number of products. "A" SM + H-Br A bunch of products. For real, hella products. 3.A. Label the stereocenters...
How to properly solve these elimination and addition
reactions
Elimination and Addition reactions Purpose: Figuring out the ways that molecules react is the province of the mechanistic chemist. By understanding the mechanisms of reactions, the chemist can manipulate the experimental variables to favor one product over another. This element of control is the province of the synthetic organic chemist. This Workshop continues to explore how we know how molecules react and how this knowledge leads to control of the products....
Help with questions 2, F on question 8a, and question 8b
please.
UUUU CHEM 2030, Sections 3.5-3.9 Reactions and Mechanisms, Introduction College Tip: Please read and take notes on the chapter before coming to class. It reduces overall anxiety and other feelings of discomfort. Additionally, it increases feelings of understanding and helps you ask more 'in-depth' questions. Instructions. Please see previous handouts for repetitive instructions. Oa. Memorize all boldface words in the chapter and be able to use them in...
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