Halogen Derivatives Questions and Answers

10 Compound A reacts with HBr via an SN1 process leading to 3 different constitutional isomers Two of these constitutional isomers are chiral such that a total of 5 distinct isomers are obtained from this reaction Draw the structures of all 5 products 41 45 OH A 42 HBr 41 43

For the questions below please indicate the expected major product for the indicated reactio If the answer for the product is a mixture of enantiomers draw one of the enantiomers and wri enantiomer If the answer is a mixture of diastereomers draw all of them Students with no printer please draw a set of numbered boxes and place answer inside 1 Br NaCN DMSO

CH 20 The major product in the reaction CH CH C Br CH CH Na CH CH X CH 1 CH3 C C CH3 2 3 CH CH C CHCH CH C H OH 2 CH CH CH CH T CH CH3 is w DO CH 4 CH CH C CH3h C CH CH3 C H

5 cis 2 Butene CH3 f CH H 1 H 2 H 4 Br 3 H C Br H C HO CH CH CH H CH H OH Br OH H HOBr OH H Br H P Identify product Pis 153 Jyr 65 cis 2 Butene HOBr H g 1 H 2 11 Br 3 4 H C Br OH H C HO CH CH3 OH Br CH CH OH H CH H H CH H Br En Pfer c s Anti F 71 Anti 72 288 270 146 18 78

Identify x and y in the following sequence C H5Br product C3H7NH2 X Question Type Single Correct Type 1 2 3 4 x KCN y LiAIH4 x KCN y H3O x CH3CI y AICI3 HCI x CH NH v HNO

Draw all the possible products of the following reaction octo Br CH OH

3 Which of the following are the products of the following reaction CH Cl Cl a CH Cl b CCl H c CC HCI d CHCI HCI 4 Use Markovnikov s Rule to predict which is major product in the following reaction pent 1 ene HBr c 2 bromopentane d 2 bromopent 1 ene a 1 bromopent 1 ene b 1 bromopentane

CI Br 3 Dr Goodchem s Graduate Student Jonathan reacted 2 bromo 2 methylbutane with a very strong base Draw the reaction showing the starting material and the products Circle the major product and give an explanation for your prediction

What is the major product of this reaction O Br tte Br Br HBr ROOR

In an alkyl halide the halogen serves 2 functions that render the alkyl halide reactive towards substitution and elimination processes One is that halgens serve as leaving groups and substitution elimination reactions can only occur when a leaving group is present What is the other reason O The halogens have pk values above zero making them weaker acids and more likely to participate in dissolution O The halogen repels electron density rendering the adjacent carbon atom nucleophilic and therefore subject to attack by an electrophile O The halogen is usually in an allylic postion and therefore does not participate in resonance making it less stable and more likely to react The halogen withdraws electron density rendering the adjacent carbon atom electrophilic and therefore subject to attack by a nucleophile

Modify the given carbon skeleton to draw the major product s of the given reaction If a racemic mixture of enantiomers is expected draw both enantiomers Note you can select a structure and use Copy and Paste to save drawing time Edit Drawing

For the following multistep mechanism select the order of arrow pushing patterns that would be needed to accomplish each step OH H HBr Br H O O 1 proton transfer 2 loss of a leaving group 3 proton transfer 1 loss of a leaving group 2 proton transfer 3 nucleophilic attack 1 proton transfer 2 nucleophilic attack 3 loss of a leaving group O 1 proton transfer 2 loss of a leaving group 3 nucleophilic attack 1 loss of a leaving group 2 nucleophilic attack 3 proton transfer

Which of the following is the correct name for this halocarbon CH3CH F difluoroethane monofluoroethane difluoromethane

What is the major organic product of the following reaction ol S Na fylg D IV Br

What is the specific gravity of chloroform when 63 67 mL of chloroform has a mass of 94 37g I I

Which of these metals will be oxidized by the ions of cobalt O Tin O Lead O Zinc Silver O copper

Match the correct reagent that will generate the products shown as the major product a b c d e Drag and drop options on the right hand side to reorder and match with items on the left Reordering may cause items on the right hand side to swap positions tBuOK tBuOH Nal H O MeOH NaCN acetone H O 1 1 NaOH H O H O HCN Nal acetone OH X

reage reactions to proceed the most efficiently 1 2 3 4 Drag and drop options on the right hand side to reorder and match with items on the left Reordering may cause items on the right hand side to swap positions 2 3 Reactions Br Reagent C Reagent H Reagent E Reagent F Reagent G Reagent B Reagent D Reagent A OMe Tott wing OH

How many different E1 products could be formed in the given molecule Hint include E and Z isomers A 1 B 2 C 3 D 4 Br

Compound A can be converted into compound G when treated with H O Starting with compound A and ending with Compound G sort the intermediates in the correct order according to the reaction mechanism Note treat resonance structures as individual steps that lead to your product Drag and drop options into correct order and submit Compound A Compound B Compound G Compound F Compound D Compound C Compound E OH Br xxxx G OH

Write and name the main product s for each of the following reactions Are these reactions stereospecific Explain Are the reactions stereoselective Explain Br Br MeOH MeOH

OH O A OB OC CH3 OH H3C C C H OH A A C D A CI H B OH OH

Provide the major organic product of the following reaction O A OB nc Br A OH Br Br B HBr xs C Br Br D Br

Which description explains this figure Br O Alkyl bromides can be converted into alkanes O Markovnikov addition of HBr is taking place O Anti Markovnikov addition of HBr is taking place O Bromination is expected to take place

Provide the product resulting from the following reaction A Br B

Provide the starting materials for the following Williamson Ether Synthesis reaction Alkyl halide Di A B Alkoxide Br Br Na O toNa O Na

7 a Write a detailed mechanism using arrows to explain only two of the following 10 points d CI CH COONa NaOEt heat 8 8

Predict the major product of the following elimination reaction CH7 OA B OC OD Br A 4 OH B C D

Br g Cl g 2 BrCl g Kc 7 0 If the composition of the reaction mixture at 400 K is BrC1 0 00653 M Br 0 00176 M and Cl 0 000323 M what is the reaction quotient Q Q reaction at 400 K How is the reaction quotient related to the equilibrium constant Ke for this reaction OQ Kc O Q Kc OQ Kc

Which of the following is least likely to react with Fluorine F O Argon Ar O Gallium Ga O lodine I O Magnesium Mg O Carbon C

2 Which reaction would be most likely to react by an SN2 mechanism CH3 A B C D E H C CI CH CI CH Cl CH CI CI OH aq CH OH DMF CH OH NO ethanol CH OH

Predict the major product s of the following reaction CH8 O A OB Br enantiomers A OC Br COOH COOH Br COOH Br Br CCIA enantiomers B Br COOH enantiomers C D Br

Select the anticipated product s from the following solvolysis reaction CH7 OI SO IV OV Br OMe MeOH heat OM 5 IV

Predict the major product s of the following reaction CH7 COI Oll OIV Br OMe OI and II MeOH OMe E IV OMe

What is the relationship between the two structures shown below CH5 CI Br H O The same compound Enantiomers H O Diastereomers O Different compounds CI Br

A Fill the table below that contains reactions of alkenes and alkynes with carbocation intermediate Reaction Hydrohalogenation Hydrohalogenation Hydrohalogenation Hydrohalogenation Acid catalyzed hydration Reactant propene propyne propyne trans but 2 ene But 2 ene Conditions 1 mol HBr 2 mol HBr H SO4 NaBr Products S 2 Bromobutane enantiomer Reaction write formulas Include stereochemistry

Which of the following best describes the relation between X and Y CH3 CH H C CI CI C H CH CH Y CH CH X A O Isomers B O Enantiomers c O Tautomers Tonomers H CH CH CH

DA OB OC OD DE OF ck the reactant to make the product using a Williamson Ether Synthesis reaction C A X E

Indicate the strongest intermolecular force present in the following substances nitrogen monoxide ammonia He methane Choose Choose Choose Choose Th

What is the major product of the following A B C Compound a a Compound b Compound c H3CC CLi b Br CH3CH 20 C

Br cl XS Naolt NH3 XS t Buok THE A co HN Colt cor 1103 2 H 02 1 Br Py 2 120 Co aljon

15 points 3 points each Q la Rank the following substrates from most 1 to least reactive 4 in an SN2 reaction Explain the reason for your choice A Order Br Explanation Order B A Br Br B C 1b Rank the following substrates from most 1 to least reactive 3 in an SN1 reaction Explain the reason for your choice Br Br CH3 C D Br

9 Draw the major products obtained in each of the following reactions indicating stereochemist where appropriate If no reaction is anticipated write no reaction

Draw eclipsed least stable conformation using Newman projection for the compound below H C H C A H CHCI H H C CI B H H H H H Me H H C H C CI C CI CHH H H C Ch D H H CHCH

How can you synthesize propyne starting with 1 1 dichloroethane Drag and drop options on the right hand side to reorder and match with items on the left Reordering may cause items on the right hand side to swap positions Step 1 Step 2 2 equiv NaNH2 NH3 3 equiv NaNH2 NH3 CH 3 Br 1 CH3CH Br 2 H 30

What is the only way to synthesize 5 methylhex 2 yne a b A B Reaction a Reaction b H C C C Br CH Br 5 methyl hex 2 yne

Which solvent would be expected to be a good choice for the reaction below Select all that apply OTS Select one or more HMPA Omethanol water acetone DMSO Nal NaOTs

Classify the electron donating group as one of the following. Weak base - Poor nucleophile Weak base - Good nucleophile Strong base - Good nucleophile Strong base Poor nucleophile

When (1R,2R,4S)-2-bromo-4-isopropyl-1- methylcyclohexane is reacted with sodium ethoxide only one product forms. Which alkene is it? (Chair conformations provided as a guide.) Product 1) Product 2)

Which of the following bases is named incorrectly? Fe(OH)3 - Iron (III) Hydroxide KOH- Potassium Hydroxide Ca(OH)₂ - Calcium Hydroxide NH3 - Ammonia Cr(OH)3 - Chromium Hydroxide