Hydrocarbons Questions and Answers

Boxes below please indicate the expected major pro Box 5 please indicate the reagents necessary to complete the indicated reaction If the answer for the product is a mixture of enantiomers draw one of the enantiomers and write 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 2 w 4 the indicated reaction For

6 A chiral C H O ether reacts with hot HI to give a C H I product Treatment of this with hot KOH in ethanol produces 1 3 pentadiene What is the structure of the original ether 10 10 2 CH A B CH Ja O C CH D H C CH

For the following reactions please deduce the structures of compounds B and C Spectral data for compound Ca summarized below 12 OH MgCl H O autoclave 230 C 2 h B C Mass spectrum m z 234 p IR Nujol 1870 sh 1940 m and 1780 s cm 1H NMR CDC13 8 0 98 d J 6 8 Hz 3H 1 08 d J 6 8 Hz 3H 1 36 m 4H 1 46 s 3H 2 60 septet J 6 8 Hz 1H 2 80 d J 9 Hz 1H 3 20 d J 9 Hz IH 6 01 d J 8 5 Hz 1H 6 10 d J 8 5 Hz IH

48 Y Answer the following by appropriately matching the lists based on the information given in paragraph Consider the compounds given in List I and the number of monohalogenated products in List LIST I P 1 P 11 R CH3 H C CH CH CH CH3 CH3 H C C C CH3 CH3 CH3 III CH3 T H C CHCH3 IV 5 H CCH2CH2CH A 1 P C II S Q R A II P C IV T S T 4 6 1 2 3 5 Which of the following options has the correct combination considering List I and List 11 Options B 1 Q D IV R LIST II Which of the following options has the correct combination considering List I and List II Options B III R D II Q

Which one is a right statement for the isomerism Choose every one Geometrical isomers are the same as the stereoisomers Structural isomers is different from the constitutional isomers There are two major groups in isomerism structural and stereo isomers One of condition for being isomers between two compounds is having the same molecular formul

a b c d 2 Only a c d 3 Only c d 4 Only b c d Correct order of heat of hydrogenation a CH CH b N c CH C CH CH d CH CH CH 1 b c d a 2 b c a d 3 a b d c c b a d 6 3 a b c d c d a CH CH b N c CH C CH CH d CH CH CH 2 1 b c d a 2 b c a d 3 a b d c 4 c b a d 2 da c d 4 b c d

11 Boiling point order of isomeric amine is 1 Primary Secondary Tertiary 2 Primary Secondary Tertiary 3 Primary Secondary Tertiary 4 Primary Secondary Tertiary

38 Select the chain propagation steps in the free radical chlorination of methane 1 Cl 2C1 2 Cl CH CH Cl H 4 3 Cl CH 4 H Cl HCl Cl 5 CH3 Cl a 2 3 5 e 3 5 CH CH3 HCl CH3Cl Cl b 1 3 6 d 2 3 4

2 Three isomeric compounds M N and P CsH 00 give the following tests i M and P react with sodium bisulfite to form an adduct ii N consumes 1 mol of bromine and also gives turbidity with conc HCl anhydrous ZnCl after prolong heating iii M reacts with excess of iodine in alkaline solution to give yellow crystalline compound with a characteristic smell iv p Rosaniline treated with sulphur dioxide develops pink colour on shaking with P The structures of M N and P respectively are A B C D M OH OH N OH e e OH P H ito D

38 When 2 Bromooctane of specific rotation 34 6 is converted into the alcohol under the conditions of first order kinetics 2 octanol of specific rotation 3 6 is obtained The conversion can be explained by 1 Free radical mechanism 2 carbonium ion mechanism 3 carbanion mechanism 4 chain reaction

CH C a CH3 2 3 dimethyl 2 butarie 0 025 mole CH3 CH3 TMAO CH3 0 034 moles TMAO trimethyl amine N oxide Product A is OsO 10 mole CH3 3 N 0 H O CH3 CH3 c CHg C CH A CH 3 N CH3 CH3 b CH C C CH3 OH OH O 11 d CH3 C C CH3 3

4 Which of the following is alkyne b C H a C H c C H d C H 2 5 Which of the following is NOT true about delocalized molecular orbitals in benzene a interaction of the unhybridized 2p orbitals in benzene leads to the formation of delocalized molecular orbital b delocalized molecular orbitals are confined between two adjacent bonding atoms c delocalized molecular orbitals actually extend over three or more atoms d electrons residing in any of these orbitals are free to move around the benzene ring 6 What is the product of the reaction of 1 mol bromine with 1 mol benzene Br CH 1 2 dibromocyclohaxa 3 5 diene 5 6 dibromocyclohaxa 1 3 diene a b c Bromobenzene d 1 1 dibromobenzene

When carbon dioxide gas is dissolved in water increasing the temperature will solubility to a increase Ob decrease

What is are the major product s of this reaction H CN O H CN CN CN CN CN CN CN ON Heat Enantiomer

What are the products of this reaction O O O OH OH H H H H ia H enantiomer enantiomer enantiomer enantiomer

Which structure is antiaromatic O H

HO p p O HO HO CH3 NH NH CH3 p HO NH

What is the product of this reaction H H H H SO4 H O HgSO4 CO

Which is are the product s of the following reaction Olonly OI and III II and IV O III only Br OCH3 CH OH II OH OCH3 IV Oli OH

Calculate the atomic mass of element X if it has 2 naturally occurring isotopes with the following masses and natural abundances X 45 X 47 44 8776 amu 46 9443 amu OA 46 84 amu OB 46 34 amu C 45 91 amu OD 46 26 amu 32 88 67 12

Step 1 Draw Kekule structures of the reagents Step 2 Mark reacting atoms group or bonds Step 3 Indicate directions of the substitutions apply Markovnikov s rule Step 4 Write Kekule structure of the product Step 5 Write the complete equation using a Kekule structures b Condensed formula la formula

29 Write structures for the following bicyclic alkanes a Bicyclo 1 1 0 butane b Bicyclo 2 1 0 pentane c 2 Chlorobicyclo 3 d 7 Methylbicyclo

Calculate the number of tetraphosphorus hexoxide molecules in a 16 8 g sample

Which of the following is a precipitation reaction A NaCl aq Lil aq Nal aq LiCl aq OB HCl aq KOH aq KCl aq H O 1 OC Zn s 2 AgNO3 aq 2 Ag s Zn NO3 2 aq D 2 Lil aq Hg NO3 2 aq Hg2l2 s 2 LINO3 aq

One mole of A Na3PO4 B Al2 SO4 3 OC S8 OD C10H8 contains the largest number of atoms

What type of bonds are present in a triple covalent bond A 1 sigma bond and 2 pi bonds OB 3 pi bonds OC 3 sigma bonds D 2 sigma bonds and 1 pi bond

What species is represented by the following information pt 47 n 62 OA Ag OB Pd C Ag OD Nd e 46

What ion corresponds to the following electron configuration Ar 11 five 3d orbitals OA Ni OB Fe OC CO3 OD Rh 4s

N CH3 The molecule above can be classified as Select Nitrogen atom is Select D and th

3 Draw the reactants and products for the reaction below 4 marks a Consider how it is possible for two products to form in this reaction and identify the major product giving your reasons for both b What type of reaction is this classified as 2 methyl 2 heptene HOH 2 methyl 2 heptanol 2 methyl 3 heptanol

Choose the major product G D 18 Choose the minor product s No minor products expected 8

d 3 methylhexanal 12 58 Draw the condensed structural pr line angle formula if cyclic for each of the following 12 3 a formaldehyde b 2 chlorobutanal c 3 methyl 2 hexanone d 3 5 dimethylhexanal

3 The American Land Title Act title insurance protects against problems that a will occur in the future b the title holder selects in advance c have been discovered though a title search d could have been discovered through a search or inspection

Reaction of ethanolic NH3 acid EtBr excess results in the formation of a 1 amine 2 amine 3 amine No reaction

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

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

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

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

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

OA OB OC Which of the following compounds absorbs the longest wavelength of UV visible light OD B D B

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

How many allylic carbons are there in this structure 02 0 3 04 415 HO

Draw a reasonable resonance contributor of resonance structures A OA OB OC OD OE B 000 D C E

Which of the following dienes contain conjugated double bonds 1 O II III O I III O II IV O I II 11 IV

In the addition of HBr to 1 butyne the electrophile in the first step of the mechanism is O the Brion O the H atom in HBr O the C sp H1 s bond of 1 butyne O the C C triple bond of 1 butyne

During many organic syntheses it is a common practice to introduce a silyl ether protecting group to mask the activity of an OH group In this example the silyl group chosen is the tert butyldimethylsilyl group Draw the product of the following transformation assuming that the tert butyldimethylsilyl Cl reagent reacts only once with the starting material M OH MO Use the we hash bond tools to indicate stereochemistry where it exists For your convenience the starting material has been drawn for you in the sketchpad OH CH3 H C C CH3 H3C SI CH3 CI Imidazole base DMF CH Cl2 Sn F K

Given the following reactions 2NO N2 O2 2NO 022NO2 is the enthalpy of the reaction of nitrogen with oxygen to produce nitrogen dioxide 2N2 402 4NO2 AH 180 kJ AH 112 kJ kJ

A sample of a gas 5 0 mol at 1 0 atm is expanded at constant temperature from 15 L to 24 L The final pressure is atm

Acetylene C H gas is often used in welding torches because of the very high heat produced when it reacts with oxygen O gas producing carbo dioxide gas and water vapor Calculate the moles of acetylene needed to produce 0 075 mol of carbon dioxide Be sure your answer has a unit symbo necessary and round it to the correct number of significant digits 0 00 x10 0 0

12 35 Acid catalyzed hydration of 3 3 dimethyl 1 butene produces Show a mechanism for this reaction 2 3 dimethyl 2 butanol