Ethers Questions and Answers

c LiAlH4 ether 34 Which of the following reactions gives an dialkyl oxonium salt a Ethyl alcohol sodium metal b Diethyl ether hydrochloric acid c Tertiary amine alkyl halide d Nitromethane sodium metal chon W ridation with per iodic acid gives

Explain the reaction shown below Include the following pieces in your explanation a Identify the electrophile and the nucleophile Draw a curved arrow mechanism for this reaction Assume an acidic work up Explain the electron flow c 1 Indicate any regiochemical or stereochemical preferences MeO LIAIH4 M 0 OH Tro

50 H3C s H C O 1 CH3 CHCH OH LIAIH A A is CH3 2 CH CH CH CH OH CH3 3 CH C OH CH3 for rough work 4 No reaction 50 3 I II IV H3C X O LIAIH H C 1 CH3 CHCH OH 4 I II III IV A A CH3 2 CH CH CH CH OH CH3 3 CH C OH CH 4 4 53

s synthesis 147 The number of methoxy groups in a compound can determined by treating it with a HI and AgNO3 c sodium hydroxide b sodium carbonate d acetic acid

Which of the following statements about Grignard reagent is not true Select one O a O b Grignard reagents RMgBr add to the carbonyl group of aldehydes and ketones An organosodium compound is not very reactive compared to a Grignard reagent Oc Grignard reagents are decomposed by water and alcohol O d Grignard reagents are prepared in ether or tetrahydrofuran THE

43 Two ionic solids AB and CB crystallize in the same lattice If rare and re r Co Ir are 0 50 and 0 70 respectively then BO A BO the ratio of edge length of AB and CD is 1 0 68 3 0 88 2 0 78 4 0 98

Follow steps 1 5 to illustrate the synthesis of the following alcohols a dipropyl ether Step 1 Draw Kekule structures of the reagents Step 2 Mark reacting atoms group or bonds Step 3 Indicate proton and hydroxide groups to be removed

9 Draw a complete curved arrow mechanism and predict the product Note that HBr won t add across the bonds in the ring like it would for a regular alkene for reasons we will get to in class soon HBr

Draw the reactant you would use to make the epoxide shown using a Sharpless epoxidation with t BuOOH and Diethyl tartrate B D Consider E Z stereochemistry of alkenes You do not have to explicitly draw H atoms Do not show stereochemistry in other cases In cases where there is more than one answer just draw one H OH

From the list of available starting materials select the reagents you would use to best prepare the following compound by a Williamson ether synthesis List your reagents by letter with no spaces or characters in between Example ao or oa OCH3 The reagents are Available Starting Materials a b ONa I i CH ONa CH ONa c 1 k Br ONa d CH ONa 1 CH Br Br e CH ONa g f CH Br n CH Br 0 Br ONa h P CH Br ONa Br

Arrow pushing Instructions MeOH Draw curved arrows to show the movement of electrons in this step of the reaction mechanism XT H SO4 OMe H3C OH

HO Arrow pushing Instructions 20 HO H Ethylene oxide is the starting material for the synthesis of 1 4 dioxepane Draw curved arrows to show the movement of electrons in this step of the reaction mechanism X OH O H O HO IO OH O H H

References Draw the reactant you would use to make the epoxide shown using a Sharpless epoxidation with t BuOOH and Diethyl tartrate H3CH C CH3 M M O OH Consider E Z stereochemistry of alkenes You do not have to explicitly draw H atoms Do not show stereochemistry in other cases In cases where there is more than one answer just draw one

Show stereochemistry only if given in the name In cases where there is more than one answer just draw one C AMARE

Dilute aqueous sulfuric acid is generally used to promote acid catalyzed hydration because these conditions have excess reactant and therefore drive the reaction towards products O these conditions have excess product and therefore drive the reaction towards products O these conditions remove product and therefore drive the reaction towards products O these conditions remove reactant and therefore drive the reaction towards products

Pick the reactants to synthesize the ether below using a Williamson Ether synthesis 2 e Reactant 1 Select Reactant II Select B 1 NaH or Na 2 II OH uhe OH C D E

Predict the major organic product in the reaction below OA OB OC CH ONS CH3 OH B CH 1 Na 2 CH3CH CH OTs CH D CH

Select the structure corresponding methoxyethane O a O b O C OH 1 CH CH CHCH CH CH CH CH CH3 0 O d CH CH CH3 1 O CH C O H

Williamsons Ether synthesis method may be used to prepare this ether phenyl 1 methylcyclohexyl ether benzylphenylether di t butyl ether Odiphenyl ether

Predict the product s for the following reaction HS HH SH I O III ON M O II OH 1 NaSH 2 H O HO Min OH NaO H OH IV Hiling

4. Select the best reaction sequence to synthesize t-butyl-propylether. a. react t-butyl alcohol with NaH, followed by reaction with t-butyl bromide b. react t-butyl alcohol with NaH, followed by reaction with propyl bromide c. react propyl alcohol with NaH, followed by reaction with t-butyl bromide d. react propyl alcohol with NaH, followed by reaction with propyl bromide

lonic compounds may have any net charge form mostly between two metalloids have zero net charge will not dissolve in water

This Is Un chemical formula for methyl tert-butyl ether (the clean-fuel gasoline additive MTBE): CH₂OC(CH3)₂ A chemical engineer has determined by measurements that there are 8.79 moles of hydrogen in a sample of methyl tert-butyl ether. How many moles of oxygen are in the sample? Round your answer to 3 significant digits.

"Intermolecular Dehydration of an Alcohol" towards unsymmetrical ether synthesis. Give an example synthesis for methyl phenyl ether using the "Williamson Ether Explain the advantages of the "Williamson Ether Synthesis" compared to an Synthesis".

How many H₂ molecules are needed to completely hydrogenate the following triacylglycerol molecule? (Figure 2) Express your answer numerically as an integer.

What direction (d or I; + or -) would you expect the enantiomer of naproxen to rotate plane-polarized light? (d). (-) (d), (+) (l). (+) (l). (-)

Draw the following (in any format) and write the molecular formula: 4) 3-iodo-2-methylhexano- 5) 1,2-dichloroethane 6) 2-chloro-4-ethylnonane 7) 4-isopropyldecane 8) 2,2,4-tribromo-3-fluorooctane 9) 1,1-difluoro-3-methylcyclohexane 10) 1-ethylcyclobutane

Dilute, aqueous sulfuric acid is generally used to promote acid catalyzed hydration because: (A) these conditions have excess reactant and therefore drive the reaction towards products. (B) these conditions have excess product and therefore drive the reaction towards products. (C) these conditions remove product and therefore drive the reaction towards products. (D) these conditions remove reactant and therefore drive the reaction towards products.

Use the activity series to determine if the following reaction will occur: Ba(s) + MgBr₂(aq) → A. yes reaction because Ba is more reactive than Mg B. yes reaction because Mg is more reactive than Ba C. no reaction because Ba is more reactive than Mg D. no reaction because Mg is more reactive than Ba

Write the correct name for each compound below. 1. ((H3C)2CH)2O:| 2. H3C-CH2-O-CH2-CH3: 3. (H3C)3C-O-CH3: 4. H3C-O-CH2-CH2-O-CH3: 5. (C6H12)2O:

Draw the structural formula of sec-butyl tert-butyl ether.