Experiment 7

Pleas explain how this process occurs. Identify SN1, SN2, E2, E1, nucleophiles and electrophiles.

1. aq. NaOH reflux NaCI H20 OH 2. HI a = Proton transfer d = Radical chain addition g = E2 Elimination b = Lewis acid/base e = Electrophilic addition h = SN1 Nucleophilic substitution C = Radical chain substitution f = E1 Elimination i = SN2 Nucleophilic substitution Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - i for your answers. 1. 2. Submit Answer Retry Entire Group 9 more group attempts remaining

H3C-C O: H ethanal :CN: and the electrophile is cyanide ion In the step you have just written, the nucleophile is slow rate-determining Ö—0—1 H3C-C-C=N; adduct

Q13

Decide which compounds from the list below are best suited for nucleophilic addition reactions and which ones are more appropriate for nucleophilic substitution reactions.

What is the nucleophile in the following reaction? 2H2 0 + CH3! → CH3OH +F + H3O* 12 O CH3I O CH3OH O H3O*

Rank the attached compounds in order of increasing reactivity in asubstitution reaction with −CN as nucleophile.

For SN1 Explain the order in which 1o (primary) alkyl halides reacted (fastest to slowest) and explain why. The 1o primary alkyl halides are: (see picture below) 1-chlorobutane 1-bromobutane 1-chloro-2butene benzylchloride

Is this an Sn2 reaction? what is the mechanism?

Rank the following reactions in order of increasing nucleophile strength: Cl-, H2O, CH3-, H2S, HS-, I-

A set of three nucleophilic displacement reactions is shown below: Br CH3 BRCH,CHCH,CH,CH,CH3 Br CH3CHCH,CH,CH,CH3 CH3CCH,CH2CH,CH3 CH3 A B H20, CH;CH,OH SN1 reaction Which reaction (A, B, or C) proceeds the fastest? Which reaction (A, B, or C) proceeds the slowest?

11

Consider the series of the trans effect: CO, CN-, C2H4 > PR3, H-, CH3- > C6H5- > NO2-, SCN-, I- > Br- >Cl- > py > NH3 > H20  What would be the major product of the following reaction? Select one:

estion 8 nydrogen and the leaving group have to be antiperiplanar in which reaction? E2 Oinversion O SN1 O SN2 Question 9 The nucleophile approaches from the opposite side of the carbon with the leaving group in which reaction mechanism? SN1 O E2 O SN1 and SN2 O SN2 17 16 A- 14 5. OO O O

Which of the following nucleophilic substitution reaction will not likely to happen? NH2 + NH2 CH3 SCH3 + CI .CI + CHSCH, H,ö: OH + HI Na* -CN CN + Nal

Draw the products to each of the following reactions and then indicate if it is sn1 sn2 E2 or E2

Choose the best reagents to complete the following reaction.

xxii

In both examples below the reactants shown are combined to bring about a nucleophilic substitution (S1, Sy2) and'or elimination (EI, E2) reaction What is the major reaction that takes place in each case? CH, CH, CH,CH,CHCCH, H20 Br NaNg CH,OH CH,CH,CHCH,CH, SN2

3. Assuming that the following reaction occurs under SN1 /E1 conditions, draw the structures of the products (there will be more than one isomer formed in each case) Page 15 of 16 CHEMISTRY 2400 EXPERIMENT 8: PRIMARY HALOALKANE: NUCLEOPHILIC SUBSTITUTION WINTER 2022 Substitution product(s) Но HBr HBr 15 Elimination product(s)

C15T09Q9684 Give the major product of the following reaction. NaOH H+ F- -NO, heat O,N HO- O,N N- H OMe F- N. Meo NO2 There is no reaction under these conditions or the correct product is not listed here.

Step 4a: Classify step. The target product is present, but the reaction is not over. The ethoxide ion has been regenerated. :0: :0: What is the key process in the next step of the mechanism? proton transfer formation of a o bond between nucleophile and electrophile loss of a leaving group carbocation rearrangement (e.g., methyl or hydride shift)