Organic Chemistry Questions

Which best describes the stereochemistry of the product s formed when the compound shown below undergoes catalytic hydrogenation with an excess of H CH OH H excess Pd Two stereoisomers are produced that are diastereomers of one another A single meso compound is the only product formed OTwo stereoisomers are produced that are enantiomers of one another O Four stereoisomers are produced

A chemist prepares a solution of vanadium III bromide VBr by measuring out 3 00 g of VBr3 into a 300 mL volumetric flask and filling to the mark with distilled water Calculate the molarity of Br anions in the chemist s solution Be sure your answer is rounded to the correct number of significant digits 1 mol x10

Given the following equation 2 KClO3 2 KCl 3 0 how many moles of O can be produced from 8 60 moles KCIO3 Report your answer with three significant figures Provide your answer below

50 I CH CH NGHI 2 8 0 8 H SO4 140 C 1 egiv e synthesis for only

What is are the major product s of the following reaction Br 1 O I II III COI O II IV O I III HBr 1 equiv Bri 11 Br K III Br IV

O Which of these will react with 12 in presence of NaOH to produce an orange precipitate S s

Here is the product obtained from Robinson Annulation What would be a suitable reagent that would react with ethylacetoacetate AAE to give this compound COOH are of os s

Rank the indicated C C bonds in order of increasing bond length H H 11 H

The equation above shows the reaction of atmospheric oxygen with metallic copper to form copper 1 oxide Indicate what type of reaction is noted here Odouble replacement None of these single replacement Odecomposition synthesis combination

Which of the following compound s have a tetrahedral arrangement of electron pairs I II and III I II IV and V III and IV and V IV and V All of these H C H H I H O H H H O H IV H N H V

What is the strongest intermolecular force possible between molecules of the following structure ion dipole interactions London dispersion forces dipole dipole interactions hydrogen bonding O covalent bonding HHHH H C C S H III HHHH

Which of these compounds of Pb2 is soluble in water OPbSO4 Pb ClO3 2 OPbS Pb OH 2 PbCl

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

Indicate the predominant intermolecular force in this molecule Ocovalent bonds Odispersion forces hydrogen bonds dipole dipole forces Oion dipole H H C N H HH

Following is the structure for Propranolol an antihypertensive drug Identify the hybridization state molecular geometry and approximate bond angle at the nitrogen atom in Propranolol OOOOO sp2 tetrahedral 109 sp2 trigonal planar 120 sp tetrahedral 109 5 sp trigonal pyramidal 109 5 sp trigonal pyramidal 180 H H HCC H H H CHHHHH OC H OH H C C H CH3 CNC CH3

Which functional group s were introduced as a result of the transformation shown below O aldehyde and ether O halogen and hydroxyl O halogen O ether and halogen O hydroxyl O hydrogen and hydroxyl O aldehyde O hydrogen ether Br OH

In the following transformation process which of the molecule is not involved HO 8 eto O HO eto eto eto Oet OH OH Oet Oet Br KOet etOH Br Br H O A

HBr 1 eqiv Provide a stepwise synthesis for only three the following Show all reagents and the ructures resulting from each step 15 points You can use any of the reagents and ny additional carbon containing compounds of your choice

What is the molecular geometry at the central atom in the molecule shown in the box trigonal planar trigonal pyramidal square planar tetrahedral Cl CO

What is the hybridization and approximate bond angle around the carbon atom in the following molecule sp 120 sp 180 sp 109 5 sp 120 sp 120 HCN

OKSO4 aq H O l KH aq HSO4 aq OK SO4 aq 2 H O l H SK aq H O l O2 g H2S aq H2O I K2O aq

Consider the equation Which of the following coefficients will balance the reaction 2 3 1 3 1 3 1 2 2 3 2 1 2 3 2 3 1 3 1 3

Predict the major product of the following reaction H O x H SO4 OIV ol OH OH HO OH IV

Which of the following statements about the reactions of alkynes is not true O When alkynes undergo two sequential addition reactions four new s bonds are formed O Alkynes undergo addition reactions O When alkynes undergo two sequential addition reactions two new s bonds and a p bond are formed O Alkynes contain easily broken p bonds

Which triene has the largest heat of hydrogenation Coll Ol DIY 11 III IV

10 The purpose of the Assignment of Interest Addendum is a to compare multiple offers b to change buyers involved in new construction c to accommodate the seller when he or she doesn t agree to the assignment d for Buyer No 1 to assign his or her position in the contract to Buyer No 2

Rank the relative strength of intermolecular forces for small molecules hydrogen bonding ion dipole dipole dipole dispersion dispersion dipole dipole hydrogen bonding ion dipole ion dipole dipole dipole hydrogen bonding dispersion ion dipole hydrogen bonding dipole dipole dispersion

Pick the structure of the major product which results when the diene shown is treated with HBr at 40 C CH3 CH OA Xx C D

ich of the following compounds has a net dipole moment of zero H F F C C 1 H H C C H F II F H H C C F F H F CFC IV F H CI C C F H V

The following compounds have similar molecular masses but vary in other physical properties H H H S H H P H H Si H H C H C 0 H 1 H H H Which has the highest boiling point OPH3 H S SiH4 HISIH CH3F

Scientists are investigating which type of fertilizer is best Which of the following methods is most likely to produce a biased result OA Let the type of fertilizer be the only variable OB Hire a scientist that works for a fertilizer company OC Set criteria for judging the effectiveness of the fertilizer D Use a team of scientists from different companies

4 A sample of mercury II bromide HgBr2 has a mass of 8 65 g Calculate the moles of HgBr2 in this sample 5 Find the mass of 0 45 moles of ammonium sulfate 6 Calculate the number of grams found in 6 53 moles of N2 gas

Rank the following in the order of their acidity 1 01 2 3 4 02 1 4 3 O2 3 1 4 2 3 4

is hexene soluble in water What are the results of your unknown justify your answer 1 Unknown 1

Which orbitals are involved in the C O sigma bond in acetone shown below Csp 05p 3 H HJ H I O O 11 C H H H

Triglycerides are used for catalysis in the body made of fatty acid monomers always unsaturated soluble in water Select all that apply Saturated fatty acids contain functional groups carboxylic acid alkenes halogen amine alkanes

2 OH A gally ginugoma nattenus to dguo108 OH B niwalion OH C OH D SO ASH

What is the best reagent for the following conversion O OLDA THF CH2 CH CHO O CH3CHO PPh3 BuLi O CH3CHO in NaOMe MeOH O H C CH OH NaOH H O 0

Which of the following represents a keto enol tautomeric pair and and OH LOH and and IV OH LOH

The compounds below all have the same formula C7H14 A B Which compound has highest surface tension Compound D NA Compound B Compound C Compound A C D

CO5 Advanced a The enzyme glucose isomerase can be used to convert glucose into fructose a much sweeter sugar The reaction is O C H 1 H C OH HO C H H C OH H C OH H C H OH Glucose Glucose isomerase OH H C H C 0 Several grades of glucose are available to be used in a fresh feed Glucose with a 1 weight percent inert impurity Glucose with a 5 weight percent inert impurity Glucose with a 10 weight percent inert impurity HO C H H C OH H C OH H C H OH Fructose The fructose can be sold for 0 44 lb It is estimated that a new plant can process about 18 000 lb hr of fresh glucose feed The process has been studied in the laboratory and about 60 of the glucole unconverted in fructose It is estimated that the annualized cost of a reactor and separator handmg 1800 lb hr of total fresh feed would cost 150 000 yr You may assume that this cost increased with the reactor size to the 0 7 power You may also assume that the separator achieves 100 separation of the glucose fructose mixture All the inerts leave with the glucose 0 220 1b 0 178 lb 0 167 lb Design a process to isomerize 18 000 lb hr of fresh glucose feed and produce pure fructose with maximum annual profit You may assume the process runs 24 hours day Derive any balances that may describe the system Define a variable x to stand in for the glucose in the fresh feed and a variable y to represent the fraction of glucose in the recycle and purge streams Let R be the size of the recycle stream and P be the size of the purge stream Substitute your balances into each other until you have one equation with x y and R undefined Using a spreadsheet set up separate tables for each value for x Then in each table define a range of y values y 01 y 02 y 03 etc You may find this easiest to have a separate row for each value of y Using your equations you should then be able to solve for R P all other variables the cost of the reactor the profit from product and the overall net gain Plot your value of y against the net gain for each of the three impurity percents Which operating condition recycle purge ratio impurity in feed etc gives you the highest possible profit Is the recycle purge ratio a value that you would expect PARS

Select the compound in which chlorine has an oxidation state of 5 O CIO3 OHCIO4 Oo OCI OCIO

Indicate which sets of reactants when mixed will form a precipitate Na3PO4 aq H SO4 aq BaCl aq LiOH aq NaCIO4 aq Fe NO3 2 aq Li S aq NiCl aq NaCl aq KBr aq

1b What is the IUPAC name for the following compound 3 points OH Smethyl

d d e O 1 equiv 1 Excess CH CH MgBr 2 H O I LIAIH 2 H O OCH3 Excess NaBH CU MaBH MeOH

Select the net ionic equation for the reaction of hypochlorous acid HOCl aq with NaOH aq None of these HOCI aq Na aq OH aq OCI aq H O l Na aq HOCI aq OH aq OCI aq H O 1 H aq OH aq H O l H aq OCI aq Na aq OH aq H O l Nat aq OCI aq

Which of the following compounds is conjugated OIV O III 11 E III IV

What diene and dienophile would react to give the products below CH3 CH3 OA B A C CHO CHO B C D B CHO

Select the type of chemical reaction that is represented by the following equation CH4 g 2 O g CO g 2 H O 1 decomposition combustion synthesis combination single replacement O double replacement

Rank the following compounds in order of decreasing basicity putting the most basic first I CEC O O III OI II C CH CH CH