Due to digitalization, computer systems have become integral to every aspect of oursociety. Not all the software and systems behind the wave of digitalization are securelydeveloped, tested, or properly configured and are, therefore, vulnerable to attacks. Thebest way to protect ourselves is through increased awareness about these threats, wherelaboratory exercises are an excellent way to teach about the practical aspects of thesethings. To better understand what makes an excellent cyber security exercise, this thesisaims to develop a CTF-based laboratory exercise for the course Ethical Hacking atKarlstad University and analyze requirements and how different factors influence thedevelopment and user experience. To do this, we set up an environment for hosting,designed and implemented the exercises, and created questionnaires to gather partici-pant data. As a result, we have created a list of 3 requirements and 4 critical factorstogether with an analysis of how they influence the development and user experience ofthe exercise. The most important results were that a correlation between difficulty andhow much the participants liked the lab was found, questionnaire options should not betoo broad since that makes the analysis of them less accurate, and distributing flags inweb environments is more complex than we first assessed.

Capture the Flag (CTF) is a common and popular type of event in the cyber security space with audiences ranging from large security conference participants to even those in middle or high school. Event participants bring their favorite set of tools and any level of knowledge they have to compete against other teams in solving cyber security related challenges. These types of challenges can range anywhere from reverse engineering programs and hacking WiFi to utilizing interesting command line commands and messing with browser developer consoles. There are plenty of general CTF events that happen throughout every month, as well as plenty of resources for those. However, CTFs focused on wireless technologies are not as prevalent. Just this last year a Wireless themed CTF, named Wireless CTF (WCTF), became publicly available to participate in. With this CTF as the target, a tool set will be put together in this thesis to help introduce some of WCTF's topics: WiFi penetration testing, POCSAG radio signal decoding, and Morse Code Signal Decoding. Tools will be chosen based on the BEAR scoring rubric, created in this thesis, to assess a given tools usability, and chosen tools will be used against challenge topics found in WCTF to test the validity of the scoring rubric and evaluate changes in a participants knowledge of each topic.

Les membranes à transport d’oxygène (OTM) sont des membranes céramiques denses qui sont capables de transporter l’oxygène de manière totalement sélective à travers un gradient de pression partielle d’oxygène. Elles peuvent être utilisées pour diminuer les émissions de gaz à effet de serre dans le cadre de la capture et du stockage du CO2 ou pour augmenter l’efficacité de l’oxydation partielle du méthane. La semi-perméabilité de l’oxygène est proportionnelle à la conductivité ambipolaire du matériau. Cependant, les OTM avec des conductivités ambipolaires élevées sont plus susceptibles de se dégrader rapidement dans les conditions d’utilisation. Pour être compétitives, les OTMs doivent donc remplir plusieurs critères, notamment avoir un flux élevé mais être aussi stables chimiquement, thermiquement, mécaniquement et être peu chères. CaTi0.9Fe0.1O3−δ (CTF) a été récemment présenté comme étant un matériau prometteur pouvant remplir ces critères et mérite d’être étudié plus en détail.Cette thèse se focalise sur les performances (mesurées par le flux d’oxygène) et la stabilité chimique et thermique du CTF. Pour améliorer les performances d’une membrane, il est nécessaire de savoir si la semi-perméation est limitée par les réactions en surface ou par la diffusion en volume. Les premiers résultats de ces travaux détaillent les étapes limitantes du transport de l’oxygène dans le CTF. En particulier, grâce à un montage expérimental spécifique et des expériences complémentaires, il a été montré que le CTF est limité à la fois par la diffusion en volume et les réactions de surfaces pour T < 750°C mais est majoritairement limité par la diffusion en volume à plus haute température. Les chapitres suivant détaillent la diffusion dans le volume et la conductivité électrique en fonction de la pression partielle d’oxygène et de la température, au vu de la chimie des défauts du CTF. Dans les conditions de fonctionnement, le CTF doit être considéré comme étant un conducteur mixte, avec une conductivité ionique qui devient prédominante pour des températures supérieures à 800°C.La seconde partie est consacrée à l’étude de la stabilité du CTF sous des atmosphères réactives, spécifiques aux OTM, qui sont connues comme provoquant des dégradations pour certains matériaux. Des tests de vieillissement sous atmosphères de CO2, CO, H2 n’ont montré aucune dégradation du flux de semi-perméation sur plusieurs centaines d’heures. Seulement une légère diminution du flux (- 25%) a été observée en présence de CO2 et de vapeur d’eau mais après cent heures sous hélium, le flux initial a été retrouvé. Des analyses DRX, MEB et Raman post-mortem n’ont révélé aucun signe notable de dégradation en surface et dans le volume. Un test sous CH4 a également été effectué, et la formation de CO, CO2, H2 et H2O a été suivie pendant des centaines d’heures. Malgré la présence de ces gaz réactifs, la même valeur du flux de semi-perméation a été retrouvée après 1000 heures de test sous méthane, témoignant d’une très bonne stabilité du CTF dans ces conditions réductrices. En conséquence, malgré des valeurs de flux relativement faibles (5×10-3 mL.min-1.cm-1 à 900°C), ce matériau est plein de promesse et son excellente stabilité sous méthane notamment peut être très intéressante pour certaines applications. / Oxygen transport membranes (OTM) are dense ceramic membranes that allow oxygen diffusion along a chemical potential gradient. OTMs can increase the efficiency of oxycombustion processes or partial oxidation of methane, resulting in lower CO2 emissions overall. The oxygen transport is proportional to the ambipolar conductivity of the OTM material. However, OTM materials with the highest ambipolar conductivity are more prone to fast degradation under operation conditions. To be competitive, OTMs must associate high oxygen transport properties but also must be chemically, thermally, and mechanically stable, and preferably not expensive. CaTi0.9Fe0.1O3−δ (CTF) has recently been shown to match these demands, appearing as a promising OTM material that is worth studying in further detail.This PhD is therefore dedicated to study the performance and stability of CTF in typical operation conditions of an OTM. To improve the performance of a membrane, it is necessary to determine if the semi-permeation is limited by surface exchange reactions or by bulk diffusion. The first results of this work will detail the nature of the limiting reaction step for oxygen transport in CTF. Specifically, CTF is co-limited by bulk diffusion and surface exchange reactions at T < 750 °C, but is mainly limited by bulk diffusion at higher temperatures. The following chapter details the bulk diffusion process and electrical conductivity in light of the defect chemistry of CTF, as a function of oxygen partial pressure and temperature. Under typical operation conditions, CTF must be regarded as a mixed ionic and electronic conductor, with increasing predominance of ionic conductivity at T > 800°C. The second part is dedicated to the stability of the CTF under atmospheric compositions typically found in standard operating conditions, known to degrade the performance of usual membrane materials. The oxygen transport of CTF is shown to remain extremely stable under CO2, CO, and H2 atmospheres over several hundred hours. Some degradation (- 25% of oxygen semi permeation flux) was observed when exposed to humidified CO2, but returning to initial values when exposed to dry helium for a hundred hour. Post-mortem XRD, SEM and Raman analyses did not show any obvious signs of surface or bulk degradation. CTF was tested for CH4 oxidation for a thousand hours and the formation of CO, CO2 and H2O was followed. Despite this reactive environment, the oxygen transport CTF membrane fully regenerates upon returning to helium atmosphere. Therefore, despite relatively low performance (5×10-3 mL.min-1.cm-1 at 900°C), this material is full of promises and especially its outstanding stability under methane can be very interesting for some applications.

Considerando-se a necessidade brasileira de se obterem fármacos a preços competitivos e usando tecnologia nacional, visamos sintetizar um fragmento do Indinavir empregando como material de partida a L-serina, um aminoácido natural de baixo custo. Desta maneira, desenvolvemos a seguinte rota, em 6 etapas: p-tosilação da serina, pelo uso de cloreto de p-tosila / NaOH; amidação da p-tosilserina, empregando-se o sal de terc-butilamônio da N-hidroxissuccinimida / DCC; ciclização da (S)-2-terc-butil-N-p-tosilserina, em condição de transferência de fase, com cloreto de p-tosila / carbonato de potássio / TEBAC; abertura regiosseletiva do anel da aziridina pela 3-picolilamina; N,N-bis-alquilação da resultante diamina, com triflato de vinildifenilsulfônio e destosilação da piperazina obtida, promovida por HBr 30%, em ácido acético. Deste modo, o fragmento (S)- N-terc-butil-4-(piridin-3-ilmetil)piperazina-2-carboxamida foi obtido em 7 % de rendimento global e pode ser usado em uma rota alternativa para a síntese do Indinavir. / Considering the Brazilian need to obtain drugs at competitive prices and using national technology, we aimed to synthesize a fragment of Indinavir using L-serine, an inexpensive natural amino acid. Thus, we developed the following route in 6 steps: p-tosylation of serine by using p-tosyl chloride / NaOH; amidation of p-tosylserine employing the N-hydroxisuccinimide terc-butylammonium salt / DCC; cyclization of (S)-2-terc-butyl-N-p-tosylserine under phase transfer catalysis with p-tosyl chloride / potassium carbonate / TEBAC; aziridine ring opening with 3-picolylamine; N,N-bisalkylation of the resulting diamine with vinyldiphenylsulfonium triflate and detosylation of the obtained piperazine promoted by HBr 30% in acetic acid. In this way, the (S)-N-terc-butyl-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide fragment was obtained in 7 % overall yield and can be used in an alternative route for the synthesis of Indinavir.

Considerando-se a necessidade brasileira de se obterem fármacos a preços competitivos e usando tecnologia nacional, visamos sintetizar um fragmento do Indinavir empregando como material de partida a L-serina, um aminoácido natural de baixo custo. Desta maneira, desenvolvemos a seguinte rota, em 6 etapas: p-tosilação da serina, pelo uso de cloreto de p-tosila / NaOH; amidação da p-tosilserina, empregando-se o sal de terc-butilamônio da N-hidroxissuccinimida / DCC; ciclização da (S)-2-terc-butil-N-p-tosilserina, em condição de transferência de fase, com cloreto de p-tosila / carbonato de potássio / TEBAC; abertura regiosseletiva do anel da aziridina pela 3-picolilamina; N,N-bis-alquilação da resultante diamina, com triflato de vinildifenilsulfônio e destosilação da piperazina obtida, promovida por HBr 30%, em ácido acético. Deste modo, o fragmento (S)- N-terc-butil-4-(piridin-3-ilmetil)piperazina-2-carboxamida foi obtido em 7 % de rendimento global e pode ser usado em uma rota alternativa para a síntese do Indinavir. / Considering the Brazilian need to obtain drugs at competitive prices and using national technology, we aimed to synthesize a fragment of Indinavir using L-serine, an inexpensive natural amino acid. Thus, we developed the following route in 6 steps: p-tosylation of serine by using p-tosyl chloride / NaOH; amidation of p-tosylserine employing the N-hydroxisuccinimide terc-butylammonium salt / DCC; cyclization of (S)-2-terc-butyl-N-p-tosylserine under phase transfer catalysis with p-tosyl chloride / potassium carbonate / TEBAC; aziridine ring opening with 3-picolylamine; N,N-bisalkylation of the resulting diamine with vinyldiphenylsulfonium triflate and detosylation of the obtained piperazine promoted by HBr 30% in acetic acid. In this way, the (S)-N-terc-butyl-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide fragment was obtained in 7 % overall yield and can be used in an alternative route for the synthesis of Indinavir.

The Compact Linear Collider (CLIC) study is a feasibility study for a new linear accelerator that aims to reach a center-of-mass collision energy of 3 TeV. To keep the length of the accelerator reasonable, a high accelerating gradient of 100 MeV/m is provided by a novel acceleration scheme, where power is extracted from a high-intensity drive beam to accelerate a high-energy main beam. The Test Beam Line (TBL) at the CLIC Test Facility 3 (CTF-3) is an experimental beamline constructed to test the technology for deceleration and power extraction of the drive beam. A Beam Loss Monitoring (BLM) system is currently under development to investigate the amount of beam loss at the TBL, with the aim of providing information about the stability of the beam under deceleration. These detectors are placed outside of the accelerator, and measure the secondary particle shower created by particles lost in the TBL. The amount of particles that can be detected by the BLM detectors was simulated using the Monte Carlo transport code FLUKA. Several different loss scenarios were simulated, in order to calculate the intensity and composition of the secondary particle shower at the detector locations. Various approximations for the sensitivity of the detectors were considered, and were combined with the simulated intensity of the shower to estimate the detector output signal per lost particle. These values were compared with data taken by the TBL BLM system, to estimate the amount of beam lost while the TBL is running.

O objetivo deste trabalho consiste na síntese de novos catalisadores quirais de transferência de fase, utilizando como matéria prima sais de piridínio derivados de &#945;-aminoálcoois ou de &#945;-aminoácidos quirais. Inicialmente, foram estudadas as reações de redução de tetrafluorboratos de 2,4,6-trimetil- e 2,4,6-trifenilpiridínio N-substituídos, que se mostraram viáveis para a obtenção de 1,2-di-hidropiridinas trifenílicas, mas conduziram a misturas de tetra-hidropiridinas no caso dos sais trimetílicos. As 1,2-di-hidropiridinas derivadas dos sais trifenílicos, em que o substituinte no átomo de nitrogênio era o grupo metila, benzila, 2-carbometoxictila ou 2-(t-butil-dimetilsilanóxi)-propila, foram submetidas a reações de Diels-Alder com anidrido maléico e / ou N-fenilmaleimida. Para as duas últimas l,2-di-hidropiridinas mencionadas, N-substituídas por grupos quirais, foram obtidos, em cada caso, dois adutos diastereoméricos, na proporção 1:1. A reação de N-alquilação dos adutos obtidos não produziu os produtos esperados, mas sim produtos de decomposição que foram atribuídos à ocorrência de reação de retro aza Diels-Alder, facilitada pela presença de uma dupla endocíclica residual. Para contornar este problema, efetuou-se a hidrogenação catalítica da referida dupla ligação, que mostrou ser estereosseletiva. No entanto, tentativas de N-alquilação dos adutos hidrogenados levaram à decomposição das isoquinuclidinas preparadas, como resultado de eliminação de Hofmann dos derivados quaternizados. / In order to synthesize a new chiral phase transfer catalyst we envisaged a synthetic route starting from pyridinium salts bearing a chiral N-substituted derived from &#945;- aminoacids or &#945;-aminoalcohols. As a first step 2,4,6-trimethyl and 2,4,6-triphenyl substituted pyridinium salts were submitted to the reduction with NaBH4. In the first case 1,2,5,6-tetrahydropyridines were obtained as main products. For the 2,4,6-triphenyl devivatives the reduction produts were 1,2-dihydropyridines. The latter compounds were reacted with two different dienophiles yielding, in each case, two diasteromeric adducts in equal proportions. Under N-alkylation conditions, these isoquinuclidenes were decomposed into the retro aza Diels-Alder produts. In order to circunvent such drawback, the Diels-Alder adducts were catalytically hydrogenated. These saturated adducts could not be N-alkylated due to the occurance of Hofmann elimination on the resulting salts.

O objetivo deste trabalho consiste na síntese de novos catalisadores quirais de transferência de fase, utilizando como matéria prima sais de piridínio derivados de &#945;-aminoálcoois ou de &#945;-aminoácidos quirais. Inicialmente, foram estudadas as reações de redução de tetrafluorboratos de 2,4,6-trimetil- e 2,4,6-trifenilpiridínio N-substituídos, que se mostraram viáveis para a obtenção de 1,2-di-hidropiridinas trifenílicas, mas conduziram a misturas de tetra-hidropiridinas no caso dos sais trimetílicos. As 1,2-di-hidropiridinas derivadas dos sais trifenílicos, em que o substituinte no átomo de nitrogênio era o grupo metila, benzila, 2-carbometoxictila ou 2-(t-butil-dimetilsilanóxi)-propila, foram submetidas a reações de Diels-Alder com anidrido maléico e / ou N-fenilmaleimida. Para as duas últimas l,2-di-hidropiridinas mencionadas, N-substituídas por grupos quirais, foram obtidos, em cada caso, dois adutos diastereoméricos, na proporção 1:1. A reação de N-alquilação dos adutos obtidos não produziu os produtos esperados, mas sim produtos de decomposição que foram atribuídos à ocorrência de reação de retro aza Diels-Alder, facilitada pela presença de uma dupla endocíclica residual. Para contornar este problema, efetuou-se a hidrogenação catalítica da referida dupla ligação, que mostrou ser estereosseletiva. No entanto, tentativas de N-alquilação dos adutos hidrogenados levaram à decomposição das isoquinuclidinas preparadas, como resultado de eliminação de Hofmann dos derivados quaternizados. / In order to synthesize a new chiral phase transfer catalyst we envisaged a synthetic route starting from pyridinium salts bearing a chiral N-substituted derived from &#945;- aminoacids or &#945;-aminoalcohols. As a first step 2,4,6-trimethyl and 2,4,6-triphenyl substituted pyridinium salts were submitted to the reduction with NaBH4. In the first case 1,2,5,6-tetrahydropyridines were obtained as main products. For the 2,4,6-triphenyl devivatives the reduction produts were 1,2-dihydropyridines. The latter compounds were reacted with two different dienophiles yielding, in each case, two diasteromeric adducts in equal proportions. Under N-alkylation conditions, these isoquinuclidenes were decomposed into the retro aza Diels-Alder produts. In order to circunvent such drawback, the Diels-Alder adducts were catalytically hydrogenated. These saturated adducts could not be N-alkylated due to the occurance of Hofmann elimination on the resulting salts.

The aim of this thesis is to evaluate the artificial intelligence model ChatGPT as a tool in the cybersecurity domain. With the purpose of analysing and facilitating understanding of the technology’s effects on possible threats. The development of AI models has a potential to alter the knowledge required to perform malicious activities. The method for evaluating ChatGPT effectiveness in aiding actors to breach a vulnerable system is a experimental capture the flag based approach. This is a type of cyber-security challenge, simulating a target system. The goal is to find and exploit vulnerabilities on the target and obtain a so-called flag to prove the breach. ChatGPT is used as an assistant and information gathering tool in the simulations. The responses collected from ChatGPT in the simulation challenges is analysed to fulfil the thesis purpose. The results shows that ChatGPT is useful as a tool. However, as with any tool, knowledge on how to use it is required. A potential threat actor do need profound comprehension and technical knowledge to make relevant queries. 41.3% of all 46 collected responses is categorised as partly usable in conjunction with previously obtained knowledge. Furthermore, to successfully breach the simulated targets the actor need to be able to modify and deploy any suggested exploit provided by ChatGPT. The findings show a correlation between more difficult capture the flag challenges and the importance of tester knowledge. The harder challenges had a higher degree of responses categorized as partly usable compared to responses deemed directly usable. In conclusion ChatGPT do not provide enough assistance at this time to increase the potential of malicious actors with limited technical knowledge. Future work in this area includes testing internet connected and newer versions of ChatGPT and further analyse the importance of prompt engineering. / Målbilden med denna avhandling är att utvärdera AI-modellen ChatGPT som ett verktyg i en cybersäkerhets-kontext. Detta syftar till att möjliggöra utökad förståelse för teknologins effekter på möjliga hot. Utvecklingen på AI-området har potentialen att förändra kunskapsbehovet hos en aktör att genomföra olika typer av cyberangrepp. Metoden för att utvärdera ChatGPT:s möjlighet till att underlätta intrång i sårbara system är ”capture the flag” baserad. Detta är en typ av cybersäkerhetsutmaning där sårbara system simuleras. Målet är att hitta och utnyttja sårbarheter i systemen för att få tag i så kallade flagor. Dessa flaggor används sedan för att bevisa ett lyckat intrång i systemet. ChatGPT kommer att användas som en assistent och för att inhämta information under dessa simuleringar. Utdata som ChatGPT genererar kommer att samlas in och analyseras för att uppnå syftet med avhandlingen. Resultaten visar att ChatGPT är ett användbart verktyg men ett verktyg som kräver långtgående förkunskaper från användaren för att uppnå effekt. En aktör behöver besitta specifika tekniska kunskaper för att ställa relevanta frågor till AI-assistenten. 41.3% av 46 insamlade svar är kategoriserade som delvis användbara tillsammans med förkunskaper hos testaren. För att lyckas genomföra de simulerade intrången behöver aktören även kunna modifiera och implementera de förslag och lösningar som ges av ChatGPT. Resultaten visar även en korrelation mellan svårare simuleringar och vikten av testarens förkunskaper. Sammanfattningsvis ger inte ChatGPT tillräckligt hög grad av assistans för att utgöra ett hot i sig. Aktörer med begränsad teknisk kännedom kan därmed i nuläget inte utöka sin potential genom att nyttja detta verktyg. Framtida arbete innefattar liknande tester av senare, internetanslutna, versioner av ChatGPT och vidare analys av så kallad ”prompt engineering”

Neste trabalho foram estudadas reações de substituição nucleofílica alifática de seis substratos halogenados, na presença de sais quaternários de amônio quirais (catalisadores por transferência de fase), derivados de alcalóides naturais. O sistema usado durante os trabalhos foi o sólido-líquido, sendo utilizado o tolueno como solvente do substrato halogenado. Os eletrófilos escolhidos para este trabalho foram, em sua grande maioria, compostos halogenados na posição alfa à carbonila e o nucleófilo foi o fenilmercapteto de sódio. A estrutura do substratos, as condições de reação e o tipo de catalisador foram variados visando-se avaliar qual a melhor condição de interação entre o catalisador e o substrato, usando-se como parâmetro comparativo o excesso enantiomérico obtido em cada caso. Os substratos foram também colocados para reagir na ausência de catalisador (\"branco de reação\") para avaliar a possibilidade de haver reações não catalisadas competindo com a reação enantiosseletiva. Tais reações diminuiriam a enantiosseletividade do processo, o que tomou imprescindível determinar sua extensão. Métodos de análise do excesso enantiomérico dos produtos de reação obtidos, por CLAE utilizando fase estacionária quiral e/ou RMN de 1H na presença de reagentes de deslocamento quirais, foram desenvolvidos para cada caso. Os resultados experimentais permitiram propor e discutir um modelo de associação catalisador/tiolato/eletrófilo, baseado em interações do tipo &#960;-&#960; e ligação de hidrogênio. / The main focus of the present work was the investigation of some aliphatic nucleofilic substitution reactions of halogenated compounds in the presence of chiral phase transfer catalyst, in a solid-liquid two phase system, using toluene as solvent. Most electrophiles were carbonylic or carboxylic derivatives bearing a halogen atom in the a-position to the carbonyl group. As for the nucleophile, sodium thiophenolate was employed in all reactions. Factors such as molecular structure of the electrophile, reaction conditions and catalyst were varied in order to optimize product enantiomeric excesses, and to gain an insight into the mode of action of the chiral catalyst in the kinetic resolution. In all cases blank experiments in the absence of the catalyst were performed, considering the possibility of a competitive uncatalyzed reaction as being responsible for lower enantiomeric excesses. Methods for determining the enantiomeric excess, based on HPLC and/or 1H-NMR, were developed for each specific product. The mechanistic and geometrical factors responsible for the kinetic resolution are analyzed in each case. The structure of the catalyst/thiolate/electrofile is discussed in terms of hydrogen bonding and &#960;-&#960; interactions.